Vacation Home Rentals By Owner In Siesta Key, FL

Sandy Cabana | Heated Pool + Walk to Crescent Beachbrbr Why You'll Love This HomebrTucked away on a quiet South Siesta Key street, Sandy Cabana is your laid-back coastal escape—just a 2-minute walk to Crescent Beach. With a private lanai, access to a heated pool, and a freshly renovated interior, this home was designed for both relaxation and reconnecting.brbr ‍ ‍ Perfect ForbrCouples, small families, or multi-gen travelers seeking walkability to the beach with the option to rent the full duplex for more space.brbr ️ Imagine ThisbrWake up to soft sunlight filtering through the palms and enjoy your morning coffee on the private screened lanai as a salty breeze drifts by. Slide open the doors to a bright, coastal-inspired living space—where pancakes sizzle in the kitchen and the promise of a poolside afternoon awaits. After a sun-filled day, rinse off the sand, pour a drink, and step back outside to catch the golden hues of a Siesta Key sunset—just two minutes from your door.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, TVbr• Bedroom 2: Queen Bed, Shared Bath, TVbr• Bedroom 3: Two Twin Beds, Shared Bathbr• Bonus: Queen Air Mattressbrbr Explore the Areabr• 0.2 Miles (2-Min Walk) to Crescent Beach Accessbr• 0.4 Miles to South Village, 1.2 Miles to Siesta Key Village – Dining, Ice Cream, Live Musicbr• 2.4 Miles to Siesta Key Public Beach Pavilionbr• 15 Minutes to Downtown Sarasota – Restaurants, Museums & Bayfrontbr• Restaurants, Cafés & Shops Within 0.5 Milesbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: This home is part of a duplex unit and includes access to the left side of the building and the shared backyard pool area. The pool is heated seasonally from November 15–April 15. Shared elements may include walls, ceilings, outdoor space, and/or amenities. Please contact us for details about shared access or to inquire about booking the entire duplex.

Sandy Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$454.8

Seahorse Cabana | Heated Pool + 2-Min Walk to Crescent Beachbrbr Why You'll Love This HomebrJust steps from the powdery sands of Crescent Beach, Seahorse Cabana is a stylish, island-inspired retreat nestled on peaceful South Siesta Key. With a newly renovated interior, screened lanai, and access to a heated pool, this home offers laid-back luxury in one of the island's most walkable beach neighborhoods.brbr ‍ ‍ Perfect Forbr Families, couples, or small friend groups seeking a relaxed Siesta Key experience with beach access just minutes away and indoor-outdoor living at its best.brbr ️ Imagine ThisbrYou start your morning in the breezy screened lanai, coffee in hand and palm fronds whispering above. A short walk leads you straight to the soft quartz sands of Crescent Beach—only two minutes from your door. After soaking up the sun and salt air, you return to your coastal-cool home, where the open layout makes it easy to prep lunch, relax in the living room, or unwind in the cool comfort of your bedroom. As twilight falls, the heated pool sparkles, laughter fills the air and you realize this is the kind of escape you'll never forget.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, Single Level, TVbr• Bedroom 2: Queen Bed, Shared Bath, Single Level, TVbr• Bedroom 3: Two Twin Beds, Shared Bath, Single Levelbr• Bonus: Queen Air Bed – Stored in Unitbrbr Explore the Areabr• 0.1 Miles (2-Min Walk) to Crescent Beach Accessbr• 0.4 Miles to South Village, 1.2 Miles to Siesta Key Village – Dining, Shopping, Ice Creambr• Walkable to Point of Rocks Snorkeling Areabr• Steps to Island Boutiques, Local Cafés & Restaurantsbr• 15 Minutes to Downtown Sarasota – Arts, Dining & Bayfrontbrbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: This home is part of a duplex unit and includes access to the right side of the building and the shared backyard pool area. The pool is heated seasonally from November 15–April 15. Shared elements may include walls, ceilings, outdoor space, and/or amenities. Please contact us for details about shared access or to inquire about booking the entire duplex.

Seahorse Cabana | Pet Friendly Home on Siesta Key w/ Heated Pool, Short Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$485.3

Casita Morning Star | A Coastal Charm with Private Pool, Walk to Crescent Beach + Villagebrbr Why You'll Love This HomebrWelcome to Casita Morning Star, a cheerful Siesta Key hideaway with its own private heated pool, tropical outdoor space, and a 3-minute walk to Crescent Beach and Point of Rocks. One half of a charming duplex, this home gives you privacy and comfort in an unbeatable beachside location.brbr ‍ ‍ Perfect ForbrIdeal for families, couples, or small groups seeking a peaceful, pet-friendly retreat with modern comforts, walkable beach access, and a private pool—not shared with the other unit.brbr ️ Imagine ThisbrWake to the sound of waves just blocks away and enjoy coffee on your screened front porch, soaking in the quiet coastal morning. After a stroll to Crescent Beach or exploring Point of Rocks, head back for a dip in your private heated pool, surrounded by lush tropical greenery and a fenced yard for total relaxation. Fire up the gas grill for dinner and unwind inside with open living space, smart TVs, and a fully equipped kitchen for home-cooked meals. With 3 spacious bedrooms and 3 full baths, everyone enjoys space and comfort in this light-filled island escape.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, TVbr• Bedroom 2: King Bed, Shared Ensuite Bath, TVbr• Bedroom 3: Full Beds, Shared Hall Bath, TVlbr• Queen Sleeper Sofa: Located in Living Room – Sleeps 2brbr Explore the Areabr• 0.2 Miles to Crescent Beach Access #13br• 0.3 Miles to Point of Rocks snorkeling spotbr• 0.2 Miles to Crescent Village (restaurants, shops, coffee)br• 1.2 Miles to Siesta Key Beach public accessbr• 1.8 Miles to Siesta Key Villagebr• Walk to Boat Rentals, Ice Cream Shops, Local Markets, and Barsbr• Quiet, Walkable Street on Southern Siesta Keybrbr⌛ Don't WaitbrCasita Morning Star offers everything you need for a beachside escape—private pool, pet-friendly policy, beach proximity, and space to sleep up to 8 guests. Your reservation includes our CottageClean™ program with a 6-hour deep clean and 35-point inspection. The pool is heated between November 15 – April 15.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free high-speed WiFi included. This is a single-level duplex unit with a shared wall but no shared amenities. Dog-friendly with a 25-pound limit and pet fee. Access to the home from Midnight Pass Rd. pool is heated between November 15 – April 15.

Casita Morning Star | Pet Friendly Home on Siesta Key, Heated Pool, Walk to Beach & South Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$914.24

Summary:brbrWelcome to coastal elegance in Sarasota! brbr- Stunning 4-bed, 4-bath pool home brbr- Gourmet kitchen with Italian Fulgor cooktop brbr- Ground-floor master suite for privacy brbr- Sun-filled flex room for versatile use brbr- Private dock access for boating enthusiasts brbr- Newly renovated outdoor space with pool brbr- Just 2 blocks to Siesta Key Beach brbr- Enjoy the best of Sarasota, from stunning beaches to cultural landmarks, all within a short drive!brbrbrbrThe Space:brbrWelcome to coastal elegance in Sarasota! This stunning 4-bed, 4-bath pool home on the coveted Palm Island offers the ultimate waterfront lifestyle with private dock access. Just 2 blocks to the beach and 10.5 blocks from Siesta Village, enjoy a prime location on a spacious, boating-friendly lot. Recently renovated, the home features a gourmet kitchen with an Italian Fulgor cooktop, a ground-floor master suite, a sun-filled flex room, and gorgeous outdoor space. Experience luxury living in Sarasota!brbrbrbrThis exquisite property promises the best of both luxury and convenience. Nestled on a large lot, it offers ample space for outdoor living, including a newly renovated pool area, full yard irrigation, and fresh sod. The home has been meticulously redesigned with a modern, open-concept layout, creating a light-filled and inviting atmosphere.brbrbrbrComfortable Accommodation:brbr- 4 spacious bedroomsbrbr- 4 modern bathroomsbrbr- Ground-floor master suite for privacybrbr- Guest room and pool bath on the main levelbrbrbrbrInterior Feeling:brbr- Gourmet kitchen with Italian Fulgor cooktopbrbr- Massive marble islandbrbr- Sleek cabinetrybrbr- Expansive living and dining areasbrbr- Sun-filled flex room for various usesbrbrbrbrOutdoor Bliss:brbr- Newly renovated pool areabrbr- Private dock access to serene canal watersbrbr- Ample outdoor space for relaxation and entertainmentbrbrbrbrDelightful Dining:brbr- Open-concept layout perfect for entertainingbrbr- Seamless flow between kitchen, dining, and living spacesbrbrbrbrProfessional Cleaning:brbr- Meticulously maintained and recently renovatedbrbr- Fresh sod and full yard irrigation for a pristine appearancebrbrbrbrJust minutes from top attractions:brbr- Siesta Key Beach – 15 minute walk drivebrbr- Siesta Key Village – 5-minute drivebrbr- St. Armands Circle – 15-minute drivebrbr- Marie Selby Botanical Gardens – 15-minute drivebrbr- Downtown Sarasota – 16-minute drivebrbr- The Ringling Museum of Art – 24-minute drivebrbrbrbrEnjoy the best of Sarasota, from stunning beaches to cultural landmarks, all within a short drive! Live the dream in Sarasota, where world-renowned Siesta Key is just a stone’s throw away.brbrbrbrGuest Access:brbrFor both short-term and long-term guest access, this beautiful Sarasota property offers the perfect blend of privacy, comfort, and convenience. Guests will have full access to the entire home, including the spacious living areas, gourmet kitchen, sun-filled flex room, and the serene pool area. The private dock along the canal is available for guests to enjoy boating or other waterfront activities. Whether you're staying for a few days or several months, this home provides everything needed for a relaxing and enjoyable stay.brbrbrbrWith beach access just two blocks away and Siesta Key Village only a short distance from the property, guests can easily explore the island, whether for a weekend getaway or an extended stay. For long-term guests, the spacious layout and modern amenities offer the comfort of home, with the added bonus of a tranquil island lifestyle. Whether you're lounging by the pool, enjoying the waterfront views, or exploring the area, this home provides an exceptional experience for both short-term and long-term stays.brbrbrbrThe Neighborhood:brbrIsland Circle is located on Siesta Key, which is known for its laid-back vibe, beautiful beaches, and upscale residences. Siesta Key is a barrier island off the coast of Sarasota, Florida, and is famous for its powdery, white sand beaches, particularly Siesta Beach, which has been ranked as one of the best in the United States.brbrbrbrThe neighborhood around Island Circle offers a mix of luxury homes, condos, and vacation rentals. It has a serene, tropical atmosphere with lush greenery, palm trees, and stunning waterfront views, which attract both full-time residents and vacationers. Many homes in this area are waterfront or have easy access to the bay and the Gulf of Mexico.brbrbrbrSiesta Key Village is also nearby, offering a variety of dining, shopping, and entertainment options, with a charming, relaxed atmosphere. The island has a strong sense of community and is known for its peaceful lifestyle while still being close to Sarasota’s cultural attractions, including museums, theaters, and fine dining.brbrbrbrIt’s a great area for outdoor activities like kayaking, paddleboarding, and biking, and it’s also renowned for its vibrant sunsets. Residents can enjoy a mix of quiet relaxation and easy access to lively local spots.brbrbrbrGetting Around:brbrGetting around Siesta Key is pretty straightforward, but since the island is relatively small, it’s important to know your options to make the most of your time there.brbrbrbrWalking & Biking:brbrbrbrMany residents and visitors prefer to walk or bike around Siesta Key. The island has a pedestrian-friendly atmosphere, and biking is a popular way to explore the area. You can find rental shops for bikes, electric bikes, and scooters. Many streets also have bike lanes, and biking to the beach or Siesta Key Village is a breeze.brbrbrbrPublic Transportation:brbrbrbrSarasota County offers a public bus service, but it might not be as frequent or convenient as other options for getting around the island. The Siesta Key Breeze is a free trolley service that runs along the main roads of the island, particularly around the busy areas like Siesta Beach and the Village. It’s a nice, eco-friendly way to travel around without the hassle of parking.brbrbrbrTaxis and Ride-Sharing (Uber/Lyft):brbrbrbrFor more flexibility or if you're looking to go off the island, taxis, Uber, and Lyft are all available in the Siesta Key area. However, during peak tourist seasons, wait times for ride-sharing services can increase.brbrbrbrCar Rentals:brbrbrbrIf you plan to explore the Sarasota area beyond Siesta Key, renting a car is a good option. There are several car rental agencies located in Sarasota, and driving to places like St. Armands Circle or downtown Sarasota is fairly easy from the island.brbrbrbrBoats and Water Transportation:brbrbrbrSince Siesta Key is surrounded by water, many residents and visitors take advantage of boating to get around, whether it’s private boats or water taxis. Siesta Key has access to the Intracoastal Waterway and the Gulf of Mexico, making it a popular spot for boating enthusiasts.brbrbrbrParking:brbrbrbrIf you’re driving, parking is generally available, but during busy seasons or peak times, spots can be limited near Siesta Beach and Siesta Key Village. It’s always best to plan ahead or use public transit/trolleys when possible.brbrbrbrIn short, getting around Siesta Key is easy, whether you prefer walking, biking, using public transit, or taking a car or boat. It really depends on your preference and how far you plan to go.brbrbrbrOther Things to Note:brbrHere are the important policies and guidelines to note for your stay:brbrbrbrCheck-in: We facilitate self-check-in, and guests are welcome to check in any time after 4 pmbrbrbrbrCheck-out: We kindly ask that you check out on or before 10:00 AM on your departure date. This allows us enough time to clean and prepare the property for the next guests.brbrbrbrNo Smoking: Smoking is strictly prohibited inside the house and within any common areas of the complex. Please respect this policy to maintain a clean and smoke-free environment.brbrbrbrNo Parties: The house is intended for quiet and peaceful stays, and hosting parties or large gatherings is not allowed. Please be considerate of the neighbors and keep noise levels to a minimum, especially during nighttime hours.brbrbrbrPets allowed: Please inform us in advance if you plan to bring pets.brbrbrbrPet Policy:brbrbrbrWe are delighted to welcome your pets to our property. To ensure a comfortable experience for both you and your furry companions, please review our policy and fees:brbrbrbrPlease ensure that your pet is well-behaved and cleaned up both indoors and outdoors. A pet fee of $50 per pet and a $200 refundable deposit is required.brbrbrbrThese policies are in place to ensure a comfortable and enjoyable experience for all guests and to maintain the integrity of the property. brbrbrbrWe offer early check-in or late check-out for an additional fee of $50brbrEarly check-in: 2pmbrbrLate check-out: 12 pmbrbrbrbrIf you have any questions or need further clarification about these policies, please contact us. We want to ensure that your stay is pleasant and in accordance with these guidelines.

Coastal Elegance Pool Home in Sarasota

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$493.25

Looking for the ultimate Siesta Key experience You’ve found it! Perfectly located just South of Morton’s in Siesta Key Village, this beautiful retreat is only a 10-minute walk to the beach and steps from everything the Key has to offer. Heated pool, smart TVs, Strong Wi-Fi, Comfy beds, sleeps up to 6 guests. Walk to top restaurants, bars, seafood spots, nightclubs, bike rentals, and live music. Free Trolley stops at Morton's every 30 min. Sun, Sand, Dining and nightlife - it's all here!brbrNEW, NEW, NEW! brThe entire building — inside and out — has been completely repainted and remodeled with brand-new furniture, a new kitchen, and all-new finishes throughout. Everything is fresh, modern, and ready for guests.brbrBe among the very first to stay — you won’t be disappointed!brbrPerfect Siesta Key Retreat – Sleeps 6, Heated Pool & All New!brbrThis newly remodeled apartment comfortably accommodates up to 6 guests with the following bedding configuration:brbr-Master Bedroom: King Bed (1)br-Guest Bedroom: Twin Bed (2)br-Living Room: Pull-Out Sofa Bed (1)brbrExclusive Amenities:brbrHeated poolbrLaundry room inside the unitbrFully stocked gourmet kitchenbrTwo parking spacesbrHigh-speed Wi-Fi & Smart TVsbrbrApproximate Drive Times to Key Locations:br5–15 min: Theater, restaurants, shopping, and morebr30 min: Sarasota-Bradenton (SRQ) Airportbr35 min: Outlet mallbr50 min: St. Petersburgbr60 min: Tampa (TPA) Airport / Port of Tampabr2 hr: Disney WorldbrbrPerfectly located just south of Morton’s Siesta Market in Siesta Key Village and only a 10-minute walk to Siesta Key Beach, this apartment combines comfort, convenience, and style for an unforgettable stay!brbrGuest accessbrOnce parked, Walk to all the Village has to offer. Beach is about a 10 min walk as well. Look for the Trolley in front of Morton's Market...comes every 30 minutes and will take you up and down the key for FREE!brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrOther things to notebrRental age restrictions:br-This property has a minimum primary renter age requirement of 25.br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- Pets are welcome, however, we do charge a $150.00 non-refundable fee per pet*.br- Smart TV system does not offer paid account services. Guest must use their account information to access.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.br-Pool/Spa Heat: Pool temperature is set to 86 degrees, however, if air temps drop below 70 degrees, pool temperature may drop significantly. Temperatures cannot be guaranteed.br-This unit is part of a Duplex. You are renting the first floor.br-Pool is shared between BOTH units.br-Snorkeling gear is not available this time.br-Quiet Hours are from 11pm to 6am. No loud noise, music, etc during these hours.br-Stays in excess of three weeks shall incur an additional cleaning fee.

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$508.6

This centrally located condo is just steps from Siesta Key Village and beautiful Siesta Key Beach! Enjoy time with the family by the heated community pool or catch some sun at the beach just 1 block away. This 2 bedroom 2 bath condo is a great space for you and your family with a king bed in the master room an en-suite bath and two twin beds in the second room with separate bath across the hallway. When entering this condo you are greeted with and open kitchen and living room with tall ceilings. Stairs must be navigated to enter this condo and also once inside as the bedrooms are on a split level.

Villa Marina (1 block from beach with pool)

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$738.64

Experience the epitome of relaxation and adventure at this canal-front haven nestled in Siesta Key. Perfect for a family getaway, this charming retreat offers everything you need for an unforgettable holiday. As you arrive at this private oasis, you will be delighted by the sight of a heated saltwater pool, inviting you to take a refreshing dip or bask in the warm Florida sun. The expansive deck provides ample space for lounging, while a cozy firepit beckons for evenings spent under the stars.

Tide's End (Pool home on canal)

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$367.21

Morning coffee on the screened balcony, afternoons in the pool surrounded by lush greenery, and evenings relaxing canal-side on the dock all await at this beautiful Siesta Key vacation rental. Whether you’re looking for outdoor adventures or city exploration, this bright and beachy 4-bedroom, 3-bathroom home is the perfect place for a coastal getaway. Walk the beach wagon down to Sarasota Beach for some fun in the sun, take the kayak out for a ride, or plan a shopping day at St. Armands Circle.brbr-- THE PROPERTY --brbrBoat Dock w/ Canal Access | Hot Tub | 0.6 Mi to Sarasota Beach | Beach Wagon & Coolers | Long-Term Rentals Welcome | Pet Friendly w/ Fee (1 Pet Max)brbrBedroom 1: Queen Bed | Bedroom 2: Full Bed, Twin Bed, Twin Daybed | Bedroom 3: California King Bed | Bedroom 4: Full Bed | Upper Living Room: Full Daybed w/ Twin TrundlebrbrINDOOR LIVING: Smart TVs, board games, books, fitness equipment, desk, printer, wine cooler, fireplaces (decorative only), dining tables, breakfast bar, en-suite bathrooms, walk-in closet, 2,300 sq ftbrOUTDOOR LIVING: Private yard, private saltwater pool, screened porch, screened balcony, deck, patio, gas grill, dining area, pool toys, outdoor shower, kayak, 2 bicyclesbrKITCHENS: Cooking basics, dishware/flatware, dishwasher, refrigerator, stove, 2-burner cooktop, microwave, drip & Keurig coffee makers, coffee grinder, blender, toaster, water filterbrGENERAL: Free WiFi, keyless entry, central heating & air conditioning, ceiling fans, linens/towels, washer/dryer, hangers, hair dryer, trash bags/paper towelsbrFAQ: Quiet hours (10:00 PM-7:00 AM), 2 exterior security cameras (facing out), optional nightly pool heat fee (paid pre-trip, applied to entire stay)brSUITABILITY: 1 step required to access, bedrooms/full bathrooms on 1st floorbrPARKING: Gravel driveway (2 vehicles), additional street parking (first-come, first-served)brbr-- THE LOCATION --brbrCOASTAL LIVING: Canal access (on-site), Sarasota Beach (0.6 miles), Siesta Beach (1 mile), Crescent Beach (3 miles), Turtle Beach (6 miles), Mote Marine Laboratory & Aquarium (10 miles)brOUTDOOR FUN: Marie Selby Botanical Gardens Downtown Sarasota Campus (6 miles), Bayfront Park (6 miles), Sarasota Jungle Gardens (9 miles), Oscar Scherer State Park (11 miles)brLOCAL HIGHLIGHTS: Sarasota Art Museum (6 miles), Sarasota Opera House (7 miles), Van Wezel Performing Arts Hall (8 miles), Ed Smith Stadium (8 miles), St. Armands Circle (9 miles), The John and Mable Ringling Museum of Art (10 miles)brAIRPORT: Sarasota Bradenton International Airport (11 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $145 fee (+fees & taxes, 1 pet max)br- No events, parties, or large gatheringsbr- Must be at least 30 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires 1 step to accessbr- NOTE: Please observe quiet hours from 10:00 PM to 7:00 AMbr- NOTE: The fireplaces are not available for guest usebr- NOTE: Your safety matters. This property features 2 exterior security cameras. Camera 1 is near the front door facing the driveway and camera 2 is on the back of the house facing the pool area. They do not look into interior spaces. The cameras will be turned off and will not record video and sound while guests are in residencebr- NOTE: There is an optional pool heat fee of $20/night (+ fees & taxes, paid pre-trip, applied to entire stay)

Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!

Siesta Key, Florida, United States

4

Bed

3

Bath

12

Sleeps

$627.13

brExclusive Amenities Include:br• Semi Private Heated Poolbr• 5 Minute Walk to Siesta Key Villagebr• 2 Minute Walk to Siesta Key Beachbr• 3 Bedrooms, 2 Full Baths (1 Master Bedroom)br• 1 King Bed, 3 Queen Beds, 1 Queen Sleeper Sofa (Sleeps 10)br• Private Balconybr• Outdoor Dining Spacebr• Putting green with 3 holesbr• Free WiFi & 4 HDTV’s with Streaming Capabilitiesbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, & Kitchen Essentialsbr• Gas Grillbr• Pet-Friendly with a Feebr• Pack & Play, sheets, and booster seat availablebrbrSea Esta | Steps to Beach + Heated Pool + Walk to VillagebrbrWhy You’ll Love This HomebrJust two minutes to the powder-soft sands of Siesta Key Beach, Sea Esta is a breezy island escape tucked into a duplex villa—walkable to all the charm of Siesta Key Village. Relax in your own private section of the home with balcony breezes, two living levels, and a semi-private heated pool in a lush outdoor space.brbrIdeal for families, couples, or friends seeking a peaceful, walkable island retreat with shared amenities but full interior privacy.brbrStart your day with a cup of coffee on the balcony, where palm trees sway in the background and you can hear the waves from just down the block. Head to the beach—just 2 minutes away—with provided chairs and a cooler. After soaking in the Gulf, return to Sea Esta’s shared heated pool, where plush loungers and a BBQ grill await. Inside, the open-concept living and dining area is perfect for unwinding, while a fully stocked kitchen makes meals a breeze. In the evenings, stream your favorite shows on any of the 4 HDTVs, or take a sunset stroll to Siesta Key Village for live music, dinner, and drinks.brbrWhere You’ll SleepbrAll bedrooms are located on the second floor (interior stairs required).br• Bedroom 1: King Bed · Shared Hall Bath · 2nd Floor, TVbr• Bedroom 2: Queen Bed · Shared Hall Bath · 2nd Floor, TVbr• Bedroom 3: Two Queen Beds · Ensuite Bath · 2nd Floor, TVbr• Living room: Queen Sleeper SofabrbrExplore the Areabr• 0.1 miles to Siesta Key Beachbr• 0.3 miles to Siesta Key Villagebr• Walkable to Dining, Drinks, Shops, Ice Cream, and Morebr• Quiet Street with Island Shuttle Access Nearby.brOther things to notebrNeed to Know: Free high-speed WiFi is included. This home is part of a duplex and shares a pool and outdoor space. All rooms are accessible only by stairs. This pool is heated between November 15 – April 15. The house is pet-friendly with fee. An exterior security camera monitors the front door.

Walking distance to Siesta Key Beach & Village w/Heated Pool & Outdoor Dining

Siesta Key, Florida, United States

3

Bed

Bath

10

Sleeps

$379.84

Enjoy a stylish stay in this fully furnished, updated 2‑bed, 2‑bath Siesta Key villa with a modern open layout, renovated kitchen, king suites, contemporary baths, 2 outdoor patios, an outdoor shower, off‑street parking, grill area, and community pool. You can take a short walk to Crescent Beach or take the free shuttle to beaches, dining, shops, and local attractions—a bright turnkey coastal retreat.brbr*** 30 day minimum for January-March required ***br*** 1 week minimum the rest of the year ***brbrOther Details:brMinimum Age to Rent: In compliance with community rules and regulations, all reservations must be made and accompanied by an adult aged 25 or older.brbrIndividuals under the age of 25 may not occupy the house unless a parent or guardian is present. Grade school or preschool-age children should not be left alone in the house or at the pool at any time.brbrMaximum Overnight Guests: The maximum occupancy is five (5) persons, including children under the age of 18.brbrTo process your rental request and issue a guest parking pass for your stay, our community association requires some basic information about all overnight guests. This includes details from your profile, such as names and phone numbers, as well as additional information like the names and ages of all guests and vehicle details. We highly encourage all guests to complete this information request to help maintain the safety and security of our community, which is especially important in case of emergencies. brbrNo Pets Allowed.brbrSiesta Key Beach consistently ranks as one of the top coastlines in the world, renowned for its 99% pure quartz-crystal sand that remains cool to the touch. In 2026, it was named the #1 Best Beach in the U.S. by U.S. News & World Report.brbrPrior Awards:br#1 Beach in the US & #4 Beach in the World - TripAdvisor 2025br#2 Beach in the US - TripAdvisor 2024br#1 Best Beach in the US - TripAdvisor 2017br#1 Best Coastal Place to Live in FL - Coastal Living Magazine 2017brFamily Beach Award - Family Vacation Critic 2013brTop Ten Beaches in the World - National Geographic 2011brbrLifestyle & LocationbrThis turnkey villa offers the perfect blend of comfort, convenience, and coastal living. Whether you're seeking a seasonal retreat or a longer‑term stay, this community provides a serene island environment with quick access to Siesta Key’s award‑winning beaches and vibrant local scene. Our fully furnished, beautifully updated 2‑bedroom, 2‑bath villa is located in the highly desirable community on Siesta Key - just minutes from the world‑famous Siesta Beach and the island’s best dining, shopping, and entertainment. Surrounded by lush tropical landscaping, this single‑story villa offers a bright, modern coastal feel with thoughtful upgrades throughout.brbr Interior Features br o Open‑concept living area with abundant natural br light, modern finishes, and comfortable furnishings br ideal for relaxing or entertainingbr o Fully renovated kitchen featuring quartz br countertops, stainless steel appliances, br contemporary cabinetry, and a seamless flow br into the dining and living spacesbr o In‑unit washer and dryer br o Two spacious bedrooms, each with a king‑size bed, br generous closet space, and west‑facing windows br perfect for capturing evening sunsetsbr o Guest bathroom with a stand‑up shower, floating br vanity, and frameless LED anti‑fog mirrorbr o Primary suite with a private en‑suite bathroom, br glass‑enclosed shower, and matching br modern finishesbrbr Outdoor & Community Amenities br o Private outdoor shower - ideal after a day at br the beachbr o Dedicated grill area for outdoor dining br and entertainingbr o Community pool just a short walk from the villabr o Free Siesta Key Breeze trolley offering easy access br to beaches, restaurants, Crescent Beach Market, br Captain Curt’s, and Siesta Key Village (driving br optional)br o Quiet, well‑maintained community known for br its tropical ambiance brbr Rental details br o Thoughtfully stocked with full kitchenware, br plush linens, soft towels, and all essential br household items to ensure a comfortable staybr o Bicycles, beach chairs, beach cart and beach br umbrella includedbr o Off street parkingbrbr---Frequently Asked Questions----brbrWe are always available to assist you with any questions you may have. To provide some immediate guidance, here are a few frequently asked questions:brbrQuestion: How far is the closest beach access from the property brbrAnswer: The nearest beach access, Public Beach Access 12, is just a short 11-minute walk (0.6 miles) away. You can find it shortly after crossing the South Bridge, opposite Captain Curt's.brbrQuestion: What is the distance to Siesta Key Village brbrAnswer: Siesta Key Village is approximately 2 miles away from the house. It offers a variety of restaurants, ATMs, a grocery store, liquor store, drug store, gift shops, ice cream shops, bars, nightclubs, salons, and coffee shops. You can also rent bikes, e-bikes, boats, scooters, snorkeling gear, fishing equipment, dive gear, and enjoy activities such as parasailing.brbrQuestion: Is a car necessary on Siesta Key brbrAnswer: In short, no! Siesta Key offers convenient transportation options, including the FREE public Siesta Key Trolley and shared ride services like Frog Hop (tips) and Jonny's Original Free Ride (tips). Walking or biking to stores, restaurants, and bars is also a viable option. However, if you wish to explore more of the greater Sarasota area, including Saint Armand's Circle, Lido Key, Long Boat Key, Venice, and Downtown Sarasota, having a personal vehicle is recommended.brbrQuestion: Can I find restaurants and bars within walking distance brbrAnswer: Yes, there are bars and restaurants located just a short ½-mile walk from the house. South Village, an area nearby, offers a convenience store, post office, drugstore, restaurants, and bars. Some of our favorite walking-distance establishments include Captain Kurt's, Sniki Tiki, and The Crescent Club.brbrQuestion: Are beach supplies provided at the property brbrAnswer: Absolutely! Our home is equipped with beach essentials, including four Tommy Bahama beach chairs, umbrella, coolers, beach towels and a beach cart.

Private Siesta Key Escape — Updated 2‑Bedroom Home Just Minutes from the Sand

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1265.31

Las VentanasbrResort-like setting with semi-private pool, rooftop deck, in-house elevator, and 5 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Terraces and Rooftop –beautiful views from five balconies and rooftop terracebr∙ Semi-private Pool – heated pool and sun shelves shared with just one other unitbr∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear waterbr∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Villagebr∙ Gulf Breezes –Ventanas means “Windows” and 3000 ft.² of windows catch sea breezes day and nightbr∙ Relaxing – 5 baths and a balcony off every bedroombr∙ Sunsets –walk 1-minute to best sunsets or just enjoy from your rooftop deckbr∙ Activities – a few free bikes and paddleboards provided, but scooter and golf cart rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for allbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy a semi private pool (shared with just one other unit), as well as private features including - four private gathering areas for your bonding enjoyment including a poolside swim-out room with wet bar, and a rooftop sundeck with ocean views and wet bar. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.brbrBedroom DetailsbrThis is a huge 4BR, you can sleep up to 13 family style. The master suite (large) has two queen beds with bath en-suite, a twin bed in the alcove and a large terrace. Bedroom #2 has a king bed and terrace. Bedroom #3 has a queen bed with bath en-suite and a terrace. Bedroom #4 is a swimout apt with a queen bed, living room, TV, full bath en suite, and private lanai poolside.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$492.34

Looking for the ultimate Siesta Key experience You’ve found it! Perfectly located just South of Morton’s in Siesta Key Village, this beautiful retreat is only a 10-minute walk to the beach and steps from everything the Key has to offer. Heated pool, smart TVs, Strong Wi-Fi, Comfy beds, sleeps up to 6 guests. Walk to top restaurants, bars, seafood spots, nightclubs, bike rentals, and live music. Free Trolley stops at Morton's every 30 min. Sun, Sand, Dining and nightlife - it's all here!brbrNEW, NEW, NEW! brThe entire building — inside and out — has been completely repainted and remodeled with brand-new furniture, a new kitchen, and all-new finishes throughout. Everything is fresh, modern, and ready for guests.brbrUpdated photos coming soon — and yes, it looks even better in person.brbrBe among the very first to stay — you won’t be disappointed!brbrPerfect Siesta Key Retreat – Sleeps 6, Heated Pool & All New!brbrThis newly remodeled apartment comfortably accommodates up to 6 guests with the following bedding configuration:brbr-Master Bedroom: King Bed (1)br-Guest Bedroom: Twin Bed (2)br-Living Room: Pull-Out Sofa Bed (1)brbrExclusive Amenities:brbrHeated poolbrLaundry room inside the unitbrFully stocked gourmet kitchenbrTwo parking spacesbrHigh-speed Wi-Fi & Smart TVsbrbrApproximate Drive Times to Key Locations:br5–15 min: Theater, restaurants, shopping, and morebr30 min: Sarasota-Bradenton (SRQ) Airportbr35 min: Outlet mallbr50 min: St. Petersburgbr60 min: Tampa (TPA) Airport / Port of Tampabr2 hr: Disney WorldbrbrPerfectly located just south of Morton’s Siesta Market in Siesta Key Village and only a 10-minute walk to Siesta Key Beach, this apartment combines comfort, convenience, and style for an unforgettable stay!brbrGuest accessbrOnce parked, Walk to all the Village has to offer. Beach is about a 10 min walk as well. Look for the Trolley in front of Morton's Market...comes every 30 minutes and will take you up and down the key for FREE!brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrOther things to notebrRental age restrictions:br-This property has a minimum primary renter age requirement of 25.br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- Pets are welcome, however, we do charge a $150.00 non-refundable fee per pet*.br- Smart TV system does not offer paid account services. Guest must use their account information to access.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.br-Pool/Spa Heat: Pool temperature is set to 86 degrees, however, if air temps drop below 70 degrees, pool temperature may drop significantly. Temperatures cannot be guaranteed.br- Island Sewer System: Our Island sewer system is very fragile. Please do not flush anything except toilet paper. No Wipes! Please discard in the trash.br-This unit is part of a Duplex. You are renting the first floor.br-Pool is shared between BOTH units.br-Snorkeling gear is not available this time.br-Quiet Hours are from 11pm to 6am. No loud noise, music, etc during these hours.br-Stays in excess of three weeks shall incur an additional cleaning fee.brbrGuest accessbrOnce parked, Walk to all the Village has to offer. Beach is about a 10 min walk as well. Look for the Trolley in front of Morton's Market...comes every 30 minutes and will take you up and down the key for FREE!brbrOther things to notebrRental age restrictions:br-This property has a minimum primary renter age requirement of 25.br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- Pets are welcome, however, we do charge a $150.00 non-refundable fee per pet*.br- Smart TV system does not offer paid account services. Guest must use their account information to access.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.br- Island Sewer System: Our Island sewer system is very fragile. Please do not flush anything except toilet paper. No Wipes! Please discard in the trash.br-Pool is shared between BOTH units.br-Snorkeling gear is not available this time.br-Quiet Hours are from 11pm to 6am. No loud noise, music, etc during these hours.br-This unit is part of a Duplex. You are renting the second floor.br-311 is located on the 2nd floor, please be mindful of noise when moving around inside the unit as guests below can hear heavy footsteps.br-Stays in excess of three weeks shall incur an additional cleaning fee.

SKV 311 - Pool, Walk to Village, Beach, Bars, Restaurants !!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$500.13

Looking for the ultimate Siesta Key experience You’ve found it! Perfectly located just South of Morton’s in Siesta Key Village, this beautiful retreat is only a 10-minute walk to the beach and steps from everything the Key has to offer. Heated pool, smart TVs, Strong Wi-Fi, Comfy beds, sleeps up to 6 guests. Walk to top restaurants, bars, seafood spots, nightclubs, bike rentals, and live music. Free Trolley stops at Morton's every 30 min. Sun, Sand, Dining and nightlife - it's all here!brbrThe spacebr NEW, NEW, NEW! brThe entire building — inside and out — has been completely repainted and remodeled with brand-new furniture, a new kitchen, and all-new finishes throughout. Everything is fresh, modern, and ready for guests.brbrUpdated photos coming soon — and yes, it looks even better in person.brbrBe among the very first to stay — you won’t be disappointed!brbrPerfect Siesta Key Retreat – Sleeps 6, Heated Pool & All New!brbrThis newly remodeled apartment comfortably accommodates up to 6 guests with the following bedding configuration:brbr-Master Bedroom: King Bed (1)br-Guest Bedroom: Twin Bed (2)br-Living Room: Pull-Out Sofa Bed (1)brbrExclusive Amenities:brHeated poolbrLaundry room inside the unitbrFully stocked gourmet kitchenbrTwo parking spacesbrHigh-speed Wi-Fi & Smart TVsbrbrApproximate Drive Times to Key Locations:br5–15 min: Theater, restaurants, shopping, and morebr30 min: Sarasota-Bradenton (SRQ) Airportbr35 min: Outlet mallbr50 min: St. Petersburgbr60 min: Tampa (TPA) Airport / Port of Tampabr2 hr: Disney WorldbrbrPerfectly located just south of Morton’s Siesta Market in Siesta Key Village and only a 10-minute walk to Siesta Key Beach, this apartment combines comfort, convenience, and style for an unforgettable stay!brbrGuest accessbrOnce parked, Walk to all the Village has to offer. Beach is about a 10 min walk as well. Look for the Trolley in front of Morton's Market...comes every 30 minutes and will take you up and down the key for FREE!brbrStarter Supplies Provided:brTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrOther things to notebrRental age restrictions:br-This property has a minimum primary renter age requirement of 25.br- Upon booking, a signed rental agreement and government issued photo identification are required prior to receiving an electronic access code to the property.br- Pets are welcome, however, we do charge a $150.00 non-refundable fee per pet*.br- Smart TV system does not offer paid account services. Guest must use their account information to access.br*Due to online booking policies, some payments may need to be submitted after the booking is reserved and confirmed. Please let us know if you have questions about the policies prior to booking.br-Pool/Spa Heat: Pool temperature is set to 86 degrees, however, if air temps drop below 70 degrees, pool temperature may drop significantly. Temperatures cannot be guaranteed.br- Island Sewer System: Our Island sewer system is very fragile. Please do not flush anything except toilet paper. No Wipes! Please discard in the trash.br-This unit is part of a Duplex. You are renting the first floor.br-Pool is shared between BOTH units.br-Snorkeling gear is not available this time.br-Quiet Hours are from 11pm to 6am. No loud noise, music, etc during these hours.br-Stays in excess of three weeks shall incur an additional cleaning fee.

SKV 309 - Heated ❤ Pool, Close to Beach, Village, Restaurants, Bars, Shopping!!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1248.7

The whole group will enjoy the easy walking access to everything Siesta Key has to offer, from its iconic beach to its vibrant restaurants and shops. Or just relax at home with a game of ping pong, a swim in the private heated pool, and outdoor dining that’s perfect for everyone.brThe spacebrExclusive Amenities Include:br• Private Heated Poolbr• 5 Minute Walk to Siesta Key Villagebr• 2 Minute Walk to Siesta Key Beachbr• 6 Bedrooms, 4 Full Bathsbr• 2 King Bed, 6 Queen Beds, 2 Queen sleeper sofas (Sleeps 20)br• 2 Screened Balconies With Seating Areasbr• 2 Full Kitchensbr• Spacious Outdoor Lounge & Dining Spacebr• Putting Green with 3 holesbr• 2 Regular & Keurig Coffee Makers, 2 Dishwashers, 2 Washers & Dryers, and Kitchen Essentialsbr• Pet Friendly with a Feebr• Pack & Play, sheets, and booster seat availablebrbrStep into island serenity at Siesta Sea Life, a spacious duplex retreat just 2 minutes to Siesta Key Beach and 5 minutes to Siesta Key Village. With dual living spaces, a private heated pool, and room for up to 20 guests, this two-story tropical haven is perfect for families and groups who crave both comfort and coastal adventure.brbrIdeal for multi-family vacations, groups traveling together, or guests seeking privacy with shared outdoor spaces—especially when booking both sides together.brbrWake up to the sound of swaying palms from one of six second-floor bedrooms, then step onto your private screened balcony with a morning coffee in hand. After breakfast in your fully equipped kitchen, load up the beach caddy and head to the powdery sands just a minute away. Afternoons are made for lounging by your heated private pool, grilling in the tropical breeze, or rinsing off in the outdoor shower before heading into the Village for dinner. End your night streaming a movie on one of 8 HDTVs, or gather outside under the stars in the spacious lounge area.brbrWhere You’ll SleepbrAll bedrooms are located on the second floor. Each side of the duplex includes:brSea Esta (Left):br• Bedroom 1: King Bed, Shared Hall Bath, TVbr• Bedroom 2: Queen Bed, Shared Hall Bath, TVbr• Bedroom 3: Two Queen Beds, Ensuite Bath, TVbr•Living room: Queen Sleeper SofabrSea La Vie (Right):br• Bedroom 4: King Bed,Shared Hall Bath, TVbr• Bedroom 5: Queen Bed, Shared Hall Bath, TVbr• Bedroom 6: Two Queen Beds, Ensuite Bath, TVbr•Living room: Queen Sleeper Sofabrbr• 0.1 Miles to Siesta Key Beachbr• 0.3 Miles to Siesta Key Villagebr• Surrounded by Casual Eateries, Ice Cream Shops, Live Music, Boutiques, and Beach Gear Storesbr• Free Island Shuttle Access NearbybrbrThis duplex home offers the flexibility of booking both sides—with separate entrances and no shared interior space.brbrOther things to notebrNeed To Know: Pool is Heated November 15 – April 15. All rooms accessible via interior stairs only. Pet-friendly with fee. An exterior security camera monitors the front door.

Perfect for large groups, Steps to the Beach. Private Pool & Putting Green.

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$601.46

Enjoy a relaxed stay at this peaceful, centrally located home just 2 minute from the beach and 5 minutes from Siesta Key Village. A heated pool and inviting outdoor space are ready for you to unwind and enjoy.brbrThe spacebrExclusive Amenities Include:br• Semi Private Heated Poolbr• 5 Minute Walk to Siesta Key Villagebr• 2 Minute Walk to Siesta Key Beachbr• 3 Bedrooms, 2 Full Baths (1 Master Bedroom)br• 1 King Bed, 3 Queen Beds, 1 Queen sleeper sofa (Sleeps 10)br• Private Balconybr• Putting green with 3 holesbr• Outdoor Dining Spacebr• Free WiFi & 4 HDTV’s with Streaming Capabilitiesbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, & Kitchen Essentialsbr• Gas Grillbr• Pet-Friendly with a Feebr• Pack & Play, sheets, and booster seat availablebrbrSea La Vie | Steps to Beach + Heated Pool + Walk to VillagebrbrbrJust two minutes to the powder-soft sands of Siesta Key Beach, Sea La Vie is a breezy island escape tucked into a duplex villa—walkable to all the charm of Siesta Key Village. Relax in your own private section of the home with balcony breezes, two living levels, and a semi-private heated pool in a lush outdoor space.brbrIdeal for families, couples, or friends seeking a peaceful, walkable island retreat with shared amenities but full interior privacy.brbrStart your day with a cup of coffee on the balcony, where palm trees sway in the background and you can hear the waves from just down the block. Head to the beach—just a minute away—with provided chairs and a cooler. After soaking in the Gulf, return to Sea Esta’s shared heated pool, where plush loungers and a BBQ grill await. Inside, the open-concept living and dining area is perfect for unwinding, while a fully stocked kitchen makes meals a breeze. In the evenings, stream your favorite shows on any of the 4 HDTVs, or take a sunset stroll to Siesta Key Village for live music, dinner, and drinks.brbrWhere You’ll SleepbrAll bedrooms are located on the second floor (interior stairs required).br• Bedroom 1: King Bed · Shared Hall Bath · 2nd Floor, TVbr• Bedroom 2: Queen Bed · Shared Hall Bath · 2nd Floor, TVbr• Bedroom 3: Two Queen Beds · Ensuite Bath · 2nd Floor, TVbr• Living Room: Queen Sleeper Sofabrbr• 0.1 miles to Siesta Key Beachbr• 0.3 miles to Siesta Key Villagebr• Walkable to Dining, Drinks, Shops, Ice Cream, and Morebr• Quiet Street with Island Shuttle Access Nearby.brOther things to notebrNeed to Know: Free high-speed WiFi is included. This home is part of a duplex and shares a pool and outdoor space. All rooms are accessible only by stairs. This pool is heated between November 15 – April 15. The house is Pet-friendly with fee. An exterior security camera monitors the front door.

Sea La Vie- Steps to the beach and Siesta Key Village w/pool and putting green

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$454.59

pThe whole group will enjoy easy access to everything from this centrally located place./pbrbrpRelax and recharge in this elevated two bedroom home. The high ceilings bring in plentiful natural sunlight with direct access to a private oversized deck. /pbrbrpThe bright and spacious layout provides plenty of space for families or couples traveling to the beach. /pbrbrpBoth Siesta Key village and Beach access 7 are less than 1/2 mile from the home. /pbrbrp2 bikes are available onsite ($40 each rental charge by Venmo) /pbrbrpThe interior is tastefully designed with functional decor. /pbrbrpPlease note this home is not suitable for young children due to the steep stairs at the entrance./pbrbrpAlso there is a separate air Bnb unit below, there are no shared spaces./pbrbrplaundry room is shared with unit below and is located in garage available daily 4-9 pm ./pbrbrpThrough air Bnb messenger or in person./pbrbrpSiesta key village/pbrbrpBike/ walk /car/ Uber/pbrbrpPlease park in front of the garage on the RIGHT side leaving room for a car to the left. /p

[lounge like locals] walk to siesta beach +bikes

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$237.88

Casita West by Siesta Key Luxury Rental Properties brbrWelcome to Casita West, a charming two-bedroom, one-bathroom Siesta Key beach bungalow located just one block from Siesta Key Beach with private beach access. This single story vacation rental offers relaxed coastal living with access to the Calini Beach Club Resort community pool, a shared patio with grill, and walkable proximity to iconic island dining. Perfect for couples, small families, or friends looking for an easy beach getaway, Casita West also includes parking for one vehicle and is dog friendly with approval. brbrHighlights br- 1-block walk to Siesta Key Beach with private beach access br- 2 bedrooms / 1 bathroom br- 1 queen bed, 2 twin beds br- Access to Calini Beach Club Resort community pool br- Shared patio with BBQ grill and outdoor dining table br- Shared washer and dryer br- Walk to restaurants including Daiquiri Deck and Captain Curt’s br- Free Siesta Key trolley nearby br- 1 parking space brbrGuests at Casita West enjoy exclusive private beach access just steps away, making beach days effortless. The community pool at Calini Beach Club Resort provides a refreshing alternative to the Gulf, with lounge chairs surrounding the deck area. The shared patio includes a grill and outdoor dining table, ideal for casual meals after a day in the sun. brbrInside, the bungalow features a comfortable living area with two sofas and a TV, creating a cozy space to relax after island adventures. The updated kitchen includes stainless steel appliances, essential cookware, and a dining area with seating for up to four guests. The open layout makes the home feel welcoming and easy to enjoy. brbrThe primary bedroom offers a queen bed and ample space for luggage and storage. The second bedroom includes two twin beds and a TV, making it a great option for children or additional guests. The bathroom is conveniently located and easily accessible from both bedrooms and the main living area. brbrRoom Details br-Primary Bedroom: Queen bed br-Second Bedroom: Two twin beds brbrCasita West is ideally located near Siesta Key Village, where guests can enjoy restaurants, ice cream shops, boutiques, and nightlife. The free island trolley provides easy access to explore more of Siesta Key without a car. Bike, kayak, and paddleboard rentals are also nearby for guests looking to enjoy the island lifestyle. brbrWith private beach access, a community pool, and walkable proximity to dining and attractions, Casita West by Siesta Key Luxury Rental Properties offers a relaxed and convenient Siesta Key vacation experience. Book your stay today and enjoy effortless island living just steps from the Gulf of Mexico!brbr- brThis property allows ONE dog with a Max weight of 35lbs with host approval prior to arrival. Please note there will be an additional pet fee associated. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund. brbr1 car maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

FRESHLY RENOVATED Adorable Bungalow Near the Beach! - Casita West

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$782.5

Peace and Relaxation! Enjoy your vacation in a spacious 5 bedroom 3.5 bathroom home on Siesta Key with a private pool and a fenced in yard. This home features 2 livings rooms, a full kitchen, and plenty of space for the whole family. Perfectly located for a trip to the beach or a short walking into the Siesta Key Village, this lovely vacation home is sure to provide plenty of wonderful memories that will have you coming back year after year!brbrMaster Bedroom: KingbrBedroom 2: KingbrBedroom 3: QueenbrBedroom 4: QueenbrBedroom 5: 2 QueensbrLiving Room: Sofa BedbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 27br*Security authorization Hold taken upon check-in. Amount: $1,500

5 bed Home W/ Private Pool on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$399.26

Immerse yourself in the magnificent Siesta Key lifestyle by staying in our modern 2BR 2.5Bath gem on a private street with gated beach access, perfect for escaping big-city crowds. Explore the city's landmarks, attractions, and pristine Siesta Key Beach. Our fantastic oasis will be waiting for you whenever you want to recharge.brbr✔ 2 Comfortable BRsbr✔ Open Design Livingbr✔ Full Kitchenbr✔ Patiobr✔ Smart TVsbr✔ High-Speed Wi-Fibr✔ Community Amenities (Pool, Beach Access, Parking)brbrSee more below!brbrThe space:brbrThe charming Siesta Key two-floor townhouse is built to provide a comfortable getaway to all visitors looking for a perfect stay. Its modern setting and outstanding facilities will offer the levels of relaxation and convenience you are looking for in a vacation home.brbrEach room has an abundance of amenities and beautiful furnishing enriched by plenty of natural light accenting the bright floors and tastefully picked decor. Every inch of space is well-used, which is best visible in the cozy living room leading into the fully equipped kitchen.brbrTwo highly comfortable bedrooms will provide all the relaxation you need after a thrilling day of Siesta Key adventures.brbrFinally, you’ll be able to catch a breath of fresh sea air on the patio or stroll to the community swimming pool and the gated beach, just a couple of steps away.brbr ★ LIVING ROOMS ★brThe living room is perfect for enjoying fun and memorable moments after an eventful day. Find your place on the comfy sofa, grab some snacks and drinks, and enjoy watching your favorite movie.brbr✔ Comfortable Sofa with Pillows (can be converted into an extra Double Bed)br✔ Smart TV with Rokubr✔ Board Gamesbr✔ Comfy Sofa Chairsbr✔ Stylish Coffee Tables & Reading Lampsbr✔ Bar Seating for 4br✔ Access to the Patiobrbr★ KITCHEN & DINING ★brCome to the fully equipped kitchen and use its many modern cooking appliances, spacious granite countertops, and ample cabinetry to create tasty homemade meals worthy of the most praised restaurants.brbr✔ Microwavebr✔ Stovebr✔ Ovenbr✔ Toasterbr✔ Blenderbr✔ Hot Water Kettlebr✔ Refrigerator/Freezer br✔ Dishwasherbr✔ Coffee Makerbr✔ Sink - Hot & Cold Waterbr✔ Platesbr✔ Glassesbr✔ Silverwarebr✔ Pots & PansbrbrEnjoy a refreshing drink on the patio while the designated family chef works their magic in the kitchen. The smells will invite you to the dining table for a tasty homemade meal.brbr✔ Dining Table brbr★ SLEEPING ARRANGEMENTS - 2 BEDROOMS + LIVING ROOM ★brRetreat to these comfortable bedrooms, designed and furnished to provide all the rest needed after a day of adventuring throughout Siesta Key, FL.brbr♛ Master Bedroom: King-Size Bed, Cozy Sofabr♛ Bedroom 2: Queen Size-Bed + Bunk Bed (Twin over Twin)br♛ Living Room: Double Sofa Bedbrbr✔ Premium Pillows, Linens, and Sheetsbr✔ Smart TVsbr✔ Closets with Hangers and Shelvesbr✔ Dressers with Spacious Drawersbr✔ Night Stands with Reading Lampsbr✔ Full-Size Mirrorsbrbr★ BATHROOMS ★brThe home offers two full relaxing baths and a convenient half bath stocked with essential toiletries and fresh towels for maximum comfort and convenience.brbr✔ Walk-In Showerbr✔ Bathtub with a Showerbr✔ Vanitybr✔ Mirrorbr✔ Toiletbr✔ Towelsbr✔ Hair Dryerbr✔ Essential Toiletriesbrbr★ PATIO ★brThe gorgeous patio offers a relaxing outdoor setting to soak up the sun and feel the neighborhood's pulse, enjoying complete privacy and the great company of your loved ones.brbr✔ Cozy Seating Area with a ParasolbrbrLook no further than our charming home for your memorable Siesta Key, FL, visit. We look forward to you experiencing its complete comfort and coziness.brbrGuest access:brbrThe townhouse is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself at home. brbrOther than the already mentioned amenities, our home also comes with the following:brbr✔ High-Speed Wi-Fibr✔ Self Check-In (Smart Lock)br✔ Travel Crib (available upon request)br✔ Air Conditioningbr✔ Washer/Dryer + DetergentbrbrThe home is part of an upscale community with private access to the swimming pool area and the gated beach that you can freely use throughout your stay.brbr✔ Swimming Pool with Sun Loungesbr✔ Private Beach Access (Chairs provided by HOA)br✔ Free Parking for ONE carbrbrOther things to note:brbr★ ADDITIONAL ACCOMMODATION ★brTraveling in a larger group, or your preferred dates are already taken You'll be happy to know that we offer additional accommodation in the community and the area. Feel free to browse our profile for a detailed list of fantastic stays.brbr★ CLEANING & SANITIZATION ★brHealth, safety, and well-being of our guests are of utmost importance. For this reason, we use a thorough cleaning process after each check-out.brbr★ NO PETS ALLOWED ★brWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable to accommodate them, nor are they permitted by our HOA.brbr★ NO SMOKING INSIDE ★brPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbr★ NO PARTIES/EVENTS ★brWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visits.brbrThank you very much for your understanding.brbrInteraction with guests:brbrWe will be accessible 24/7 for our guests via phone, text, or the VRBO app. brExpect a quick and prompt response. We give our guests space but are available for every inquiry. brbrContact us now so we can begin arranging your perfect vacation!brbrThe neighborhood:brbrThe townhouse is nestled on a private street with a gated beach access point in Siesta Key, a tropical haven on the west coast of Florida that embodies the essence of paradise—known for its powdery white sands, crystal-clear waters, and laid-back atmosphere.brbrSiesta Key is renowned for having some of the most breathtaking beaches in the United States. Siesta Beach, in particular, has earned acclaim for its powdery, quartz-crystal sands, which stay cool even on the warmest days. Sunset at Siesta Beach is a spectacle not to be missed, with hues of orange and pink painting the sky as the sun dips below the horizon.brbrBeyond the beaches, Siesta Key offers a wide range of outdoor activities. Kayak through the calm waters of the mangrove tunnels at South Lido County Park, paddleboarding in the Gulf of Mexico, or embark on a fishing charter to catch your dinner. Nature enthusiasts will appreciate the lush landscapes and wildlife in the nearby Myakka River State Park.brbrSiesta Key Village is the heart of the island's dining, shopping, and entertainment scene. Stroll along quaint streets with boutiques, surf shops, and art galleries. Savor fresh seafood at beachfront restaurants, sip tropical cocktails at vibrant bars, and enjoy live music under the stars.brbrThe warm waters surrounding Siesta Key beckon adventure seekers to explore. Try windsurfing, jet skiing, or parasailing for an adrenaline rush. Scuba diving and snorkeling enthusiasts will be delighted by the vibrant underwater world of the Gulf. For a more leisurely experience, rent a boat, explore the Intracoastal Waterway, or take a dolphin-watching tour.brbrCome and discover the beauty and tranquility of this coastal gem, where every day feels like a beach day in paradise.brbrHere are some places of interest you'll be looking to visit during your stay.brbr✔ Siesta Key Beach (3 min away)br✔ Crescent Beach (3 min away)br✔ PARASAIL SIESTA (4 min away)br✔ Siesta Key Watersports (5 min away)br✔ Siesta Key Village (5 min away)br✔ Marie Selby Botanical Gardens (15 min away)br✔ Sarasota Jungle Gardens (24 min away)br✔ Lido Key Beach (25 min away)br✔ South Lido County Park (25 min away)br✔ Mote Marine Laboratory & Aquarium (25 min away)br✔ St. Petersburg (55 min away)br✔ Tampa (1h 5 min away)br✔ Fort Myers (1h 15 min away)brbr***Distance times are calculated if traveling by car.brbrGetting around:brbrIf you arrive by car, you will be happy to know that we offer one free parking spot in the back of the townhouse. However, if you would like to avoid driving during your stay, there are many convenient, easily accessible transportation options close to our home.brbr✔ Siesta Key Breeze Trolley (stop on top of the street leads you to Siesta Key Village for free). This service runs continual loops around the island from 8AM - 10PM.br✔ Taxibr✔ Lyft & UberbrbrIf you are flying in/out of the area, the best way would be at the below airport:brbr✔ Sarasota Bradenton International Airport (25 min away)

Sunny & Comfy ~ Steps to Siesta Key Beach ~ Pool!

Siesta Key, Florida, United States

Bed