Vacation Home Rentals By Owner In Siesta Key, FL

$453.97

Beautiful 2 Bedroom Lake View Home on Siesta Key!

Siesta Key, Florida, United States

Beautiful lake view, 2-bedroom, 2-bath home on Siesta Key! This home is a spacious unit, featuring a king bed in the master and 2 twin beds in the second bedroom. This home sleep up to 6 guests. Outside your living room is a 20 ft long deck with a stunning full-length view of the lake! A brief walk from the condo to sand, is the beautiful Siesta Key Beach! This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. Relax on our world-famous Siesta Beach, or take a trip to Siesta Key Village, which offers endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1: KingbrBedroom 2: 2 TwinsbrLiving Room: Sleeper SofabrbrAdded 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: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $1,000

2

Bed

2

Bath

6

Sleeps

$623.39

/ Nightly

Private Vacation Home

New and Rare Waterfront Gem: 4-Bedroom Pool Home Walk to Beach & Village

Siesta Key, Florida, United States

Discover the ideal seasonal retreat at this beautifully appointed 4-bedroom waterfront home, perfectly situated on a waterfront corner lot just a 10-minute walk (or 5-minute bike ride) to Siesta Key Village. Vibrant restaurants, lively bars, and charming boutique shopping are all within easy reach. The world-renowned Siesta Key Beach is also just minutes away, making this location unbeatable for both relaxation and adventure.brbrThis contemporary home features an extra-large pool, perfect for soaking up the Florida sunshine. Inside, you'll find a spacious, well-equipped kitchen ideal for the novice to experienced chef. The modern finishes and ample accommodations include a king bed and three queen beds, as well as 4 bathrooms. brbrAdditional amenities include air conditioning, heating, WiFi, a washing machine, dryer, an iron, a hair dryer, and smart TVs throughout for your entertainment. There’s also a grill for outdoor dining.brbrWith a 30-day minimum rental requirement, this home provides the perfect setting for an extended stay on Siesta Key. The owners (hi!) work in hospitality so they will be there if you need them, and won't be if you don't! brbrDon’t miss your chance to enjoy the best of Siesta Key in this brand-new listing—book your getaway today!

4

Bed

4

Bath

8

Sleeps

$741.52

/ Nightly

Private Vacation Home

Double King Suites Bike to Beach, Pool & Mini Golf

Siesta Key, Florida, United States

Summary:brbrBike to world-class Siesta Key beach in minutes. Private pool, mini-golf course, hammock & game room make this home the perfect “fun, chill, repeat” base for families or friends.brbrbrbrEscape to the Salt & Sol House- your ultimate beach getaway on Siesta Key. A tastefully designed luxe coastal boho space just minutes from the white sands crystal quartz sand of Siesta Key Beach. This newly designed vacation rental offers everything for your perfect Florida escape. Enjoy indoor outdoor living, a heated pool, private putting green, bikes for exploring, hammocks in the shade, and twinkling string lights that create unforgettable evenings. Experience pure relaxation with resort-style amenities and luxury in paradise.brbrbrbrThe Space:brbrSalt & Sol is the place to be if you’re looking to experience true Southwest Florida coastal living. Whether you’re here for a family getaway, couples retreat, or to explore the best of Siesta Key, this vacation getaway offers the ultimate blend of style, comfort, and convenient location. We thought about every detail that would make your stay truly memorable. brbrbrbr☆ Luxury Coastal Home Minutes from Siesta Key Beach & Villagebrbr☆ 3 Bedrooms (Includes Private Guest Suite)brbr☆ 3 Full Bathrooms + 1/2 Bathbrbr☆ Full Indoor/outdoor Living Experiencebrbr☆ Heated Pool & Lounge Areabrbr☆ Private Putting Greenbrbr☆ Turf Yard for Kids to Playbrbr☆ Essential Amenities for Babiesbrbr☆ Sandbox with Sandtoys for Kidsbrbr☆ Hammocks in the Shadebrbr☆ Entertainment Room in the Garagebrbr☆ String Lights for Magical Eveningsbrbr☆ Fully Stocked Kitchenbrbr☆ Tesla Chargerbrbr☆ Bikes for Guest Usebrbr☆ High-Speed Wi-Fibrbr☆ Smart TVsbrbr☆ Free On-Site Parkingbrbrbrbr Why It’s Great & Who It’s ForbrbrbrbrThis home is ideal for:brbrbrbrFamilies - kids will love the mini-golf, pool, sandbox and game roombrbrCouples - Double master king suites perfect for two couples traveling togetherbrbrGroups of friends - plenty of space, plenty to do, and just a short ride to the beach brbrBeach lovers & day-trippers - bike to America's #1 beachbrbrVacationers who want “everything in one place” - no need to choose between comfort, fun, and location.brbrbrbr★ Living Room ★brbrbrbrRelax in style in the bright, open-concept living area with coastal-inspired décor.brbrbrbr☆ Open Layout with Pool Viewsbrbr☆ The Sliding doors open up so you can experience the true Siesta Key lifestyle with indoor outdoor livingbrbr☆ Smart TV with Streaming Appsbrbr☆ Large Sectional Sofabrbr☆ Coffee Table brbr☆ Toy bins for kids brbr☆ Board Games & Puzzlesbrbrbrbrbrbr★ Kitchen & Dining ★brbrbrbrCook, dine, and connect in a modern, fully stocked kitchen. Featuring quartz countertops, stainless steel appliances, and an elegant dining space perfect for entertaining or family meals.brbrbrbr☆ Fully Equipped Kitchenbrbr☆ Large Dining Table for 8brbr☆ Coffee Bar with Keurig Coffee Maker & K-Cupsbrbr☆ Cookware, Bullet Blender, Utensils & Dishesbrbrbrbr★ Bedrooms ★brbrbrbr♛ Primary Suite - Sleeps up to 3 guestsbrbr☆ King Bed with Luxury Cotton Linensbrbr☆ Murphy Bedbrbr☆ Walk In Closet w/ His/Her Bath Robesbrbr☆ En-Suite Double Vanity Bathroombrbr☆ Pool Accessbrbr☆ Dedicated Work Spacebrbrbrbr♛ Guest Bedroom - Sleeps up to 6 guestsbrbr☆ Queen Bunk Bed for 3 w/ USB Charging Nightstand brbr☆ Twin bunk bed with pull out trundle for 3 brbrCloset for Storagebrbrbrbr♛ Guest Suite - Sleeps up to 3 guests brbr☆ Custom Flamingo Designbrbr☆ Private Entrancebrbr☆ French doors with pool accessbrbr☆ King Bedbrbr☆ Trundle with Twin XL mattressbrbr☆ Kitchenette w/ Coffee Barbrbr☆ En-suite bathroom w/ custom tile work brbrbrbr★ Bathrooms ★brbrbrbrAll bathrooms are beautifully designed with modern finishes, plush towels, and essential toiletries for your comfort.brbrbrbr☆ 3 Full Bathroomsbrbr☆ Walk-In Showersbrbr☆ Vanity Mirrors w/ Heat/Light Adjustments brbr☆ Toiletries & Fresh Towelsbrbrbrbr★ Outdoor Oasis ★brbrbrbrYour private paradise awaits — soak in the heated pool, tee off on the backyard putting green, or unwind under the glowing string lights as the sun sets.brbrbrbr☆ Heated Pool with Lounge Areabrbr☆ Private Putting Greenbrbr☆ Turf Yard for Kidsbrbr☆ Sandbox with sand toys for kids brbr☆ Hammocks Under the Palmsbrbr☆ Beverage Fridge brbr☆ Comfortable Outdoor Cushioned Lounges with Firepitbrbr☆ String Lights for Eveningsbrbr☆ Outdoor Grillbrbrbrbr★ Entertainment Room ★brbrbrbr☆ PacMan Arcade Centerbrbr☆ Ping Pong Tablebrbr☆ Dart Board brbrbrbrGuest AccessbrbrbrbrGuests have access to the entire property, including the main home, guest suite, and all outdoor amenities.brbrbrbrOther Things to NotebrbrbrbrEarly check-in or late check-out may be available upon request (fees apply).brbrbrbr Please Respect the NeighborhoodbrbrWe are located in a peaceful, quiet, family friend neighborhood full of great neighbors who help make this community special. To keep it that way, we ask that all guests be considerate and respectful during their stay.brbrbrbr Please Respect Our Quiet Hours: 10:00 PM – 8:00 AMbrbr• Please keep voices, music, and outdoor noise to a minimum.brbr• No loud gatherings or parties are permitted at any time.brbr• If spending time outdoors at night, please keep noise low and lights minimal.brbr• Failure to comply with the city’s noise ordinance can result in fines to the occupants.brbr• Be Mindful when arriving early or latebrbrbrbr★ Additional Rules ★brbrbrbr☆ All inventory is accounted for. Guests are responsible for any damages during their stay.brbr☆ Smoking of any kind is prohibited inside; a $250 cleaning fee applies if found.brbr☆ No parties or unregistered overnight guests.brbrbrbr★ Security Cameras ★brbrExterior cameras are located at the driveway and front door for safety — no interior cameras.brbrbrbr★ Pet Policy ★brbrPets are not allowed. If an undisclosed pet is found, a $500 cleaning fee applies.brbrbrbrGuest Access:brbrThe house is exclusively for you to enjoy during your stay, so relax, unwind, and make yourself at home. You'll have access to the entire home, backyard and garage.brbrbrbrThe Neighborhood:brbrLocated in a quiet neighborhood under a canopy road only minutes away from Siesta Key Beach and Siesta Key Village.brbrbrbrGetting Around:brbr4 Minute Drive to Siesta Key Beach brbr4 Minute Drive to Siesta Key Village brbr(Traffic permitted) brbr20 minutes from Sarasota/Bradenton Airportbrbr18 minutes from Downtown SarasotabrbrbrbrOther Things to Note:brbr Book your stay at Salt & Sol — your coastal paradise awaits! brbrbrbrInteraction with Guests:brbrWe won't be available in person, and prefer to keep all communication through the app. However, a phone number is provided in the case of non-911 emergencies.

Bed

Bath

Sleeps

$1280.58

/ Nightly

Private Vacation Home

Waterfront Home w/ Dock, Heated Pool/Spa, Rooftop w/ Gulf Views

Siesta Key, Florida, United States

Dry Dock by Siesta Key Luxury Rental Properties brbrWelcome to Dry Dock, a refined canal-front Siesta Key luxury rental offering the perfect blend of waterfront adventure and relaxed island living. This six bedroom, six and a half bath house is located just a three-minute walk to Siesta Key Beach and within easy walking distance of Siesta Key Village. With a private pool and hot tub, shared dock access, elevator, and rooftop deck with Gulf views, Dry Dock is ideal for large families, multifamily groups, and extended stays seeking effortless coastal comfort near the best of Sarasota’s beach attractions. brbrHighlights br- 3-minute walk to Siesta Key Beach br- Canal-front home with shared dock access br- 6 bedrooms / 6.5 bathrooms br- 4 king beds, 6 twin beds (bunk beds) br- Private pool and hot tub br- Rooftop deck with Gulf views br- Elevator access to all living levels br- Ping pong table br- Two kayaks and beach wagon br- Outdoor dining area with BBQ grill br- Washer and dryer in unit br- Dog friendly with approval br- Four parking spaces br- Professional Linen Program brbrThis canal front retreat offers resort style outdoor living designed for both relaxation and play. The backyard features a private pool and hot tub surrounded by lounge seating, perfect for cooling off after a day at the beach. Guests can enjoy direct access to the shared dock for kayaking, paddleboarding, boating, or fishing, with two kayaks included for easy water exploration. The rooftop deck provides an elevated island experience, offering sweeping views toward the Gulf. The covered patio adds another layer of outdoor comfort with a bar, seating for five, outdoor television, and ping pong table. brbrDry Dock offers two levels of spacious living above the garage, easily accessed by an elevator. The open concept living area is designed for gathering, featuring an oversized sectional sofa where guests can relax after beach days or enjoy movie nights together. Sliding doors lead to a second level balcony overlooking the canal. The fully equipped kitchen features stainless steel appliances, generous counter space, and an island with seating for six, making it ideal for preparing group meals. The dining area comfortably seats twelve, allowing all eighteen guests to dine together in one shared space, perfect for family meals, takeout nights, or board games. brbrThe primary bedroom offers a serene retreat with calming coastal tones, generous closet space, and an ensuite bathroom with a shower and tub combination. Additional bedrooms feature king beds with ensuite bathrooms, many offering walk-in showers and private or shared balcony access overlooking the canal. Younger guests will love the thoughtfully designed bunk rooms, each offering a bright, beachy atmosphere and plenty of space to relax. These rooms are ideal for kids or teens traveling together and maintaining the same level of comfort and quality found throughout the home. Each bunk room includes its own ensuite bathroom, providing privacy and convenience for larger groups. brbrRoom Details br- Primary Bedroom (Second Level): King bed, ensuite bathroom with shower and tub combination br- Second Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, private balcony br- Third Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, shared balcony br- Fourth Bedroom (Third Level): King bed, ensuite bathroom with walk-in shower, shared balcony br- Fifth Bedroom (Third Level): Twin over twin bunk bed, ensuite bathroom with shower and tub combination br- Sixth Bedroom (Second Level: Two twin bunk beds, ensuite bathroom with shower and tub combination brbrDry Dock is dog friendly with prior approval and an additional non-refundable pet fee. This home is located near popular island favorites including Daiquiri Deck and Gilligan’s Island Bar. Guests will also appreciate the option to rent the neighboring unit, Salty Dog, which shares a mirrored layout, ideal for doubling accommodations for larger groups. brbrWith canal front access, a private pool and hot tub, rooftop Gulf views, and a walk to beach location, Dry Dock by Siesta Key Luxury Rental Properties offers an elevated beach getaway designed for unforgettable group vacations. Book your stay today and experience the best of Siesta Key waterfront rentals and luxury coastal living! brbr- brSiesta Key Luxury Rental Properties Pet Policy: Dogs are allowed under certain conditions and ALL animals, including service animals, must be disclosed and approved before arrival. We cannot accept cats. Please note that an additional non-refundable pet fee will be charged upon approval by Siesta Key Luxury Rental Properties. Weight limit of 50 lbs max total for 1 or 2 dogs combined. No dangerous breeds are allowed. Please see our Siesta Key Luxury Rental Properties Rental Policies for complete details. brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment. 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. brbrIf you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry. One of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon.

Bed

Bath

Sleeps

$926.68

/ Nightly

Private Vacation Home

Spacious Siesta Key Paradise-Canal front, private pool, walk to SK Beach/Village

Siesta Key, Florida, United States

Beaches, Boating and Bistros! Live the island lifestyle in this spacious 5 bedroom, 4 bathroom house located on desirable Palm Island on Siesta Key. Lounge in the heated pool and spa or enjoy your favorite libation at your private Waterfront Tiki Bar. brbrThe best location on Siesta Key. 7 minute walk to Siesta Key Beach, 9 minute walk to Siesta Key Village. Large private heated pool with hot tub.brbrHouse is located on the Grand Canal with access to the Intercostal Waterway, with private dock. Large private deck right on the canal for relaxing or entertaining. Also has Tiki Bar adjacent to pool and dock, with large fire pit area. Large heated pool has ample chase lounges, chairs and dinning area that seats 10. Pool area also has large spa whirlpool.brbrThe 5 bedrooms will accommodate 10 people. Master suite and 3 other bedrooms on main(second) floor, along with 3 full bathrooms. Master suite is equipped with Spa/Hydro Massage Tub. The lower floor has a bonus area with large bar room and large rec room with high quality ping pong table. Ground floor also has one bedroom and full bathroom. brbrHuge open living space, with massive kitchen and dinning area that seats 10 or more. Dinning area leads right into family area with two full couches and 70' TV. This area is connected to a bar top table area for drinks/eats over looking the pool and canal area. On the other side is a large sitting area for reading or just relaxing and admiring the views of pool and canal area. Both family area and sitting area lead to very large deck by way of large sliding glass doors that open completely up.brbrThe large second floor deck overlooks the pool, the canal and the Tiki area. Deck has large six seat table, with patio couch and coffee table, in addition to a sitting area with Adirondacks chairs.brbrLocation is a quick walk to Siesta Key Beach. Beach cart, beach chairs and umbrella provided. Also, just a few minute walk to the Siesta Key Village, filled with tons of fun restaurants, bars, and shopping.brbr

Bed

Bath

Sleeps

$582.31

/ Nightly

Private Vacation Home

Siesta Key Waterfront House + Pool & Boat Dock!

Siesta Key, Florida, United States

Summary:brbrWaterfront luxury in the heart of Siesta Key. This 3-bed, 2-bath private pool home offers a rare combination of canal-front serenity and walk-to-beach convenience. Enjoy a private boat dock with direct Gulf access, kayaks you can drop in your backyard, relax on the sunlit lanai, and unwind with tranquil water views (spot manatees!). Just minutes from Siesta Key Beach, dining, and village shops—this is coastal Florida living done right. Bikes, Kayaks, Golf Clubs, and Beach Supplies all provided!brbrbrbrThe Space:brbrWATERFRONT | PRIVATE POOL | PRIVATE DOCK | BIKES & KAYAKS | MINUTES TO SIESTA KEY BEACH brbrbrbrWelcome to one of the most sought-after setups on Siesta Key—a canal-front, 3-bedroom pool home where you can walk to the #1 beach in the U.S., launch kayaks from your backyard, and park your boat at the house with direct access to Sarasota Bay and the Gulf.brbrbrbrThis 3-bed, 2-bath waterfront retreat sleeps up to 8 guests and combines the relaxed luxury of island living with unbeatable access to boating, beaches, dining, and Siesta Key Village.brbrbrbr PLEASE NOTE: There may still be ongoing construction at the neighbors house. As a result, there may be construction noise and materials. It can sometimes get very loud. We also cannot control whether neighbors choose to initiate construction/renovation projects. As a result - we do not issue refunds due to construction, construction noise, or amenity closures. brbrbrbrWhat Guests Love (from our reviews!):brbrbrbr⭐ “Beautiful home that felt like home”brbr⭐ “Even better than expected”brbr⭐ “Fished off the back dock and kayaked right from the house”brbr⭐ “Super clean, amazing pool, and incredible scenery”brbr⭐ “The team was responsive and went above and beyond”brbrbrbr✅ Why Book Our Home:brbrbrbr✔ RARE walk-to-beach + PRIVATE BOAT DOCK combination (no cost to park) brbr✔ Private pool with covered lanai overlooking the canalbrbr✔ Direct boating access—bring your boat or enjoy the kayaks (we provide kayaks!)brbr✔ Quiet WATERFRONT neighborhood, minutes from Siesta Key Villagebrbr✔ Bikes, kayaks, pool, dock—everything included, no add-onsbrbrbrbrSLEEPING & COMFORT brbrbrbr✓ 3 bedrooms: 2 King beds + 1 Queen bunk bedbrbr✓ Sleeps up to 8 guests comfortablybrbr✓ Hotel-quality linens, extra pillows, and hangersbrbr✓ Central air conditioning and heating throughoutbrbrbrbrBATHROOMSbrbrbrbr✓ Primary ensuite with dual sinks and walk-in shower (no tub)brbr✓ Second bathroom with Jack & Jill layout and tub/shower combobrbr✓ Towels, toiletries, and hair dryer providedbrbrbrbrKITCHEN & DININGbrbrbrbr✓ Fully equipped kitchen with dishwasher, oven, range, microwave, refrigerator, freezer, and kettlebrbr✓ Cookware, utensils, and dining essentials includedbrbr✓ Indoor dining plus outdoor grill for poolside mealsbrbr✓ Keurig & Coffee provided brbrbrbrENTERTAINMENT & AMENITIESbrbrbrbr✓ Comfortable living area with TV and high-speed Wi-Fibrbr✓ Private large screened POOL with solar heating brbr ‍♀️Guests are not permitted to access or adjust the pool heater themselves. If you would like the pool heated, please request it at least 72 hours in advance. Pool heating is available for an additional fee of $45 per day, and the owner will activate it remotely. Unauthorized use or activation of the pool heater without advanced notification will result in additional fees.brbr✓ Covered lanai with seating and canal viewsbrbr✓ Private dock with lift, plus kayaks ready to launchbrbr✓ Ideal for boating, fishing, swimming, and relaxing outdoorsbrbr✓ Bikes provided FREE for guests! brbrbrbrPARKING & LOCATIONbrbrbrbr✓ 2-car garage plus driveway parkingbrbr✓ Short walk to Siesta Key’s world-famous white-sand beachbrbr✓ Minutes to restaurants, cafes, bars, and shops in Siesta Key Villagebrbr✓ Peaceful canal-front setting with quick access to open waterbrbrbrbrGuest Access:brbrGuests have full access to the entire home , including the private pool , lanai ☀️, boat dock, outdoor seating , kitchen , laundry , and 2-car garage — all just minutes from Siesta Key’s beaches ️ and village shops ️brbrbrbrThe Neighborhood:brbrLocated in the desirable Siesta Key area, just steps from the island’s famous white-sand beaches ️. Explore charming local shops ️, cafés ☕, and restaurants ️ in Siesta Key Village. Perfect for boating , fishing , or paddleboarding in the calm canals. Relax and enjoy a safe, friendly, and vibrant waterfront community.brbrbrbrGetting Around:brbrEasily explore Siesta Key and Sarasota by bike , car , or on foot . Beach trolley service is nearby for quick trips to Siesta Key Village and local beaches ️. Free parking is available for guests, and the home’s private dock makes boating and water adventures simple and convenient.brbrbrbrOther Things to Note:brbr⏰ Check-in / Check-out:brbrStandard check-in and check-out times are in place to allow our cleaning team to prepare every unit to our 5-star standard. Early check-in may be available upon request—just send us a message! Note, there is a per hour fee!brbrbrbr⚠️ A digital rental agreement MUST be signed prior to arrival, and you will need to provide a copy of a legal ID with a verification selfie. This cannot be done in person.brbrbrbr⚠️ Damage Waiver: Every reservation includes our Damage Waiver Program — you’re covered for up to $500 in accidental damage during your stay. Just relax and enjoy your trip, knowing little mishaps are taken care of. (Note, this is not insurance and does not replace travel or liability insurance; this self-funded protection covers up to $500 in accidental damage to contents only. Examples included linens, towels, and winebrbrbrbr Pest Note: We treat regularly, but Florida may have occasional pests. No refunds are issued for pest sightings, though we’re always happy to address concerns.brbrbrbr⚠️ Please be aware that certain situations beyond our control may occur, including construction or noise outside the unit, temporary closure of amenities, utility or city repairs, or other issues on neighboring properties or units. As these circumstances are beyond our control, we are unable to provide refunds for any relatedbrbrbrbr Pack ’n Plays must be requested in advance and are subject to availability. As these items are shared across our units, we kindly ask that you request one at the time of booking to confirm availability.brbrInteraction with guestsbrbrbrbrPLEASE NOTE:brbr- Additional supplies may be available conditionally, but we cannot guarantee anything. If you run short, there are plenty of nearby stores to purchase more supplies! The towels provided are intended for approximately the first 3 days of your stay. If you need to refresh them, you’re welcome to use the in-unit washer and dryer, or the laundry facilities available on the property (please note that laundry fees may apply). For stays of 5 nights or longer, you may request replacement towels, and we’ll do our best to provide them based on availability.brbrbrbr✓ ITEMS LEFT BEHIND. If a guest leaves personal items behind and requests their return, they are responsible for a $25 service fee plus packaging and shipping costs. We are not responsible for any loss or damage to left items once the guest has departed.brbrbrbrInteraction with Guests:brbrWe respect your privacy but are just a message or phone call away if you need anything during your stay. Whether it’s questions about the condo, local recommendations, or assistance with check-in/check-out, we’re happy to help. Our goal is to make your stay as comfortable and enjoyable as possible!

Bed

Bath

Sleeps

$944.49

/ Nightly

Private Vacation Home

Private Heated Pool, Steps to Siesta Key Village/Beach, Family/Pet Friendly

Siesta Key, Florida, United States

Bimini Breeze by Siesta Key Luxury Rental Properties brbrWelcome to Bimini Breeze, a fully remodeled 2-bedroom, 2-bath ground floor home in the heart of Siesta Key, less than a block away from Siesta Key Village and Siesta Key Beach! This vacation rental has a resort style pool that is inviting and perfect for relaxing while enjoying the warm sun. Walk less than five minutes to the shimmery white sands of the best Gulf beach on Siesta Key or Siesta Key Village for dining and shopping. This Siesta Key vacation rental is ideal for couples, small families, or friends seeking easy beach access and island nightlife. brbrHighlights br• 4-minute walk to Siesta Key Beach br• 2 Bedroom / 2 Bathroom br• 1 King, 1 Full/full bunk, 1 Queen sleeper sofa – sleeps 8 br• Private resort style pool with sun shelves br• 3-minute walk to Siesta Key Village shops and dining br• Dog friendly with host approval br• Beach chairs and beach towels included br• Professional linen programbr• Private backyard seating and outdoor dining for six br• 3 Parking spaces brbrEnjoy your private pool with generous space and sun shelves for lounging, while the provided beach gear allows for easy days on the sand. Relax outside and enjoy the warm Florida sunshine or explore delicious local dining and shopping with Siesta Key Village nearby. brbrThe bright open living room includes blue hues, comfortable seating, and large TV opens through sliding glass doors to the backyard and pool. Fully equipped kitchen stainless steel appliances, large island seating for four, and coastal decor makes meal prep effortless. Dining and living areas designed for relaxed island living. brbrThe primary bedroom features a king bed, TV, ample closet space, and an ensuite with a walk-in shower. The second bedroom offers a full over full bunk ideal for kids or extra guests with access to the hall bathroom providing a shower/tub combination. The queen sleeper sofa in the living room provides additional sleeping space. brbrRoom Details br• Primary Bedroom: King with ensuite bathroom with walk-in shower br• Second Bedroom: Full over full bunk bed br• Living room: Queen sleeper sofa brbrA washer and dryer are provided in the house. Bike rentals or the free island trolley will help you explore the key. Siesta Key Village is steps from your doorstep, with local shops, cafes, restaurants, and nightclubs for live music and drinks. Whatever your vacation speed is, this home makes island living a breeze. brbrBook now and experience an effortless island living at Bimini Breeze by Siesta Key Luxury Rental Properties, walk to the beach and Siesta Key Village, relax by your private pool, and enjoy coastal comforts. Reserve your dates today! br brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. 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. brbr3 cars 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.

Bed

Bath

Sleeps

$1436.08

/ Nightly

Private Vacation Home

Huge Yard with Heated Pool, Steps to Beach - The Pool House

Siesta Key, Florida, United States

The Pool House by Siesta Key Luxury Rental Properties brbrThe Pool House by Siesta Key Luxury Rental Properties is a refined five bedroom, four bath vacation home designed for families and friends seeking effortless coastal living near the beach and village. Located in the desirable Sunset Pointe neighborhood, this Siesta Key luxury rental is just a three-minute walk to Sunset Beach and a short stroll to Siesta Key Village restaurants and shops. With a private heated pool and spa, stylish outdoor living spaces, and airy coastal interiors, this home delivers the perfect balance of relaxation and island fun. brbrHighlights br• 3-minute walk to Sunset Beach br• 5-minute walk to Siesta Key Village dining and shopping br• 5 Bedrooms / 4 Bathrooms br• 4 King beds, 1 Twin over Full bunk bed with Twin trundle, 2 Queen sleeper sofas br• Private heated pool with spa br• Outdoor dining and seating area with TV br• Poolside loungers and BBQ grill br• Beach chairs and beach wagon br• Dog friendly with host approval br• Washer and dryer brbrStep outside to a private tropical oasis designed for year round enjoyment. The sparkling pool and spa are surrounded by comfortable loungers, creating a resort style setting perfect for sunny afternoons or relaxed evenings. The covered outdoor seating and dining area with TV and BBQ grill invites guests to gather for meals, movie nights, or post beach relaxation. brbrInside, The Pool House features an open concept layout with upscale coastal decor and a bright, airy feel throughout. The living area offers plush seating and a welcoming space for movie nights or downtime after a day at the beach. The chef’s kitchen is fully equipped with stainless steel appliances, generous counter space, and a large island with seating, making it ideal for preparing meals together. Next, it's a formal dining area featuring a spacious wood dining table with woven coastal-style seating and warm pendant lighting, creating a relaxed and inviting setting for memorable group dinners. brbrThe home offers a thoughtful bedroom layout that works well for multifamily stays. On the first floor, three primary bedrooms each feature king beds, with select rooms offering ensuite bathrooms with walk-in showers for added privacy and convenience. Upstairs, two additional bedrooms create a flexible retreat with a loft-style feel. One bedroom features a twin over full bunk bed with a twin trundle, perfect for younger guests, while the other offers a king bed and access to a furnished private balcony. These bedrooms share a full bathroom with a walk-in shower. brbrRoom Details br• First Bedroom (1st Floor): King bed, ensuite bathroom with walk-in shower br• Second Bedroom (1st Floor): King bed, ensuite bathroom with walk-in shower br• Third Bedroom (1st Floor): King bed br• Fourth Bedroom (2nd Floor): Twin over Full bunk bed with Twin trundle br• Fifth Bedroom (2nd Floor): King bed, furnished balcony br• Living Area: Two Queen sleeper sofas brbrThe Pool House is ideally situated on Avenida Messina, placing guests just a few homes from the shoreline and within easy walking distance of Siesta Key Village. This Siesta Key vacation home includes an in home washer and dryer, beach chairs and a wagon for easy beach days, and a private pool area perfect for relaxing when not exploring the island. With host approval prior to arrival, dogs are welcome, making this a pet-friendly option for guests traveling with furry companions. brbrCombining a prime Sunset Pointe location, private poolside living, and spacious coastal interiors, The Pool House by Siesta Key Luxury Rental Properties is an ideal choice for families and groups looking to experience the best of Siesta Key. From beach walks at sunset to poolside afternoons and village dining just steps away, this home sets the stage for an unforgettable island escape. Book your stay at The Pool House today and experience luxury coastal living on Siesta Key! brbr- br*Please note- the fireplace is not a working fireplace and is for decorative purposes only. brbrThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell, active video surveillance on the exterior public approach areas, and the pool equipment and gate. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. 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.

Bed

Bath

Sleeps

$1467.61

/ Nightly

Private Vacation Home

Heated Pool/Spa w/ Waterslide. Rooftop Deck w/ Gulf Views. Water/Dock Access

Siesta Key, Florida, United States

Aloft on Canal by Siesta Key Luxury Rental Properties brbrWelcome to Aloft on Canal, an upscale eight bedroom, six and a half bath Siesta Key luxury rental designed for effortless coastal living and memorable group getaways. Located just a four-minute walk to Siesta Key Beach and directly across from the canal with dock access, this refined beach house blends island-inspired interiors with resort style outdoor living. With a private heated pool and spa, waterslide, rooftop deck, elevator, and generous parking, this home is ideal for large families, multifamily groups, and extended stays near Siesta Key Village and local favorites along Midnight Pass Road. brbrHighlights br- 4-minute walk to Siesta Key Beach br- 8 bedrooms and 6.5 bathrooms br- 6 king beds, 1 full bed, 6 twin beds br- Private heated pool with waterslide and spa br- Canal and dock access across the street br- Rooftop deck and multiple balconies br- Elevator access to all levels br- Game room with ping pong table br- Dog friendly with approval br- 4 parking spaces brbrStep outside to your tropical outdoor oasis, where a private heated pool takes center stage with a rock waterslide, sun shelf, and inviting spa. The backyard is designed for relaxed island days and lively evenings, complete with outdoor seating and a BBQ grill for casual meals after the beach. Canal access across the street opens the door to kayaking, paddleboarding, and boating adventures, adding a waterfront element that elevates this Siesta Key vacation home with pool. The rooftop deck offers a peaceful retreat above it all, perfect for sunset moments after a day spent enjoying the Gulf Coast. brbrInside, this home showcases modern coastal decor and a bright, open concept layout ideal for gathering. The living area features ample seating and a large TV, creating a comfortable space for movie nights or downtime between beach outings. Sliding glass doors bring natural light and connect seamlessly to outdoor living areas. The gourmet kitchen is fully equipped with high end appliances and two large islands, making it easy for multiple cooks to prepare meals together. Whether hosting family dinners or casual breakfasts before heading to the beach, this kitchen supports effortless entertainment. brbrThe primary suite on the third floor offers a king bed, private balcony, and a spa inspired ensuite bathroom with a walk-in shower and a soaking tub, creating a serene retreat. Additional bedrooms feature king beds with ensuite or shared bathrooms, many with balcony access, maintaining a refined and restful atmosphere throughout. The home also includes bunk accommodations designed with younger guests in mind, offering flexibility without sacrificing comfort. Bathrooms are thoughtfully appointed with walk-in showers and polished finishes, ensuring convenience for larger groups. brbrRoom Details br- Primary Bedroom (Third Floor): King bed, private balcony, ensuite bathroom with walk-in shower and stand-alone tub br- Second Bedroom (Third Floor): King bed, balcony access, ensuite bathroom with walk-in shower br- Third Bedroom, Third Floor): King bed, ensuite bathroom with walk-in shower, connects to fourth bedroom br- Fourth Bedroom (Third Floor): Twin over full bunk bed with twin trundle br- Fifth Bedroom (Second Floor): King bed, balcony access, ensuite bathroom with walk-in shower br- Sixth Bedroom (Second Floor): King bed, balcony access, jack-and-jill bathroom with walk-in shower br- Seventh Bedroom (Second Floor): King bed, jack and jill bathroom with walk-in shower br- Eighth Bedroom: Two twin bunk beds brbrThis home participates in our Professional Linen Program, providing hotel quality linens and towels that are freshly laundered for every stay. Dog-friendly accommodations are available with prior approval and an additional fee. Guests will enjoy being close to Siesta Key Village, with shops and restaurants for a one of kind entrainment. With easy access to attractions and the Gulf, this location offers both relaxation and adventure. brbrFrom its private pool and canal access to its spacious layout and walk-to-beach location, Aloft on Canal by Siesta Key Luxury Rental Properties delivers coastal comfort with elevated style. Book your stay today and experience the best of Siesta Key luxury rentals for your next beach getaway! brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. 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. brbrIf you have any questions concerning our home, rates, amenities, policies, or anything else, please send us an inquiry, and one of our professional reservationists and property managers would be happy to help answer your questions. You are a couple of clicks away from paradise, and we look forward to seeing you soon.

Bed

Bath

Sleeps

$655.74

/ Nightly

Private Vacation Home

Dog Friendly, Private Heated Pool, Steps to the Beach and Shops! -Aruba

Siesta Key, Florida, United States

Aruba by Siesta Key Luxury Rental Properties brbrWelcome to Aruba! A fully refreshed 3-bedroom, 2.5-bath home located in the heart of Siesta key, just a short 4-minute stroll from Siesta Key Beach and within easy walking distance of Siesta Key Village! Walk less than five minutes to the shimmery white sands of the best Gulf beach on Siesta Key or Siesta Key Village for dining and shopping. With a beautifully large, private pool, BBQ grill, and dog friendly accommodations, Aruba is ideal for families or friends who want effortless beach days and relaxed island entertainment. brbrHighlights br• 4-minute walk to Siesta Key Beach br• 3 Bedroom / 3 Bathroom br• 2 Kings, 1 twin/twin bunk with twin trundle, 1 queen sleeper sofabr• Short walk to Siesta Key Village shops and restaurants br• Private pool with covered outdoor dining area br• BBQ grill br• Dog friendly (with approval and fee) br• Washer and dryer on site br• 3 parking spaces br• Near free island trolley brbrPrivate backyard pool for swimming and lounging, including a covered patio with table and grill for alfresco meals and entertaining. With a dog friendly policy, enjoy the tropical atmosphere with your furry friends. Stroll to the beach and bring the provided beach chairs or head to Siesta Key Village and explore the nearby attractions. brbrThe bright living area offers multiple sofas, side chairs, a TV, and a bar top for casual snacks and games. The fully equipped kitchen features stainless steel appliances, plenty of cabinets, and an adjacent dining room with pool views, perfect for group meals and easy flow to the outdoor space. brbrThe primary bedroom includes a king bed, premium mattress, TV, and ample storage. The second bedroom also has a king bed, premium mattress, and TV. The third bedroom is a nautical themed bunk room with two twin over twin bunks plus a twin trundle and an ensuite with a walk-in shower, ideal for children. The hall bath includes shower/tub combination, easily accessible from both the primary and second bedrooms. The living room queen sleeper sofa adds extra sleeping space, with access to the hall bath and half bath which includes a washer and dryer. brbrRoom Details br• Primary Bedroom: King bed br• Second Bedroom: King bed br• Third Bedroom: Twin-over-twin bunk with twin trundle, ensuite bathroom with walk-in shower br• Living room: Queen sleeper sofa brbrThis home includes a washer and dryer, hair dryer, iron and ironing board, as well as 3 parking spaces. Walk to beach activities like snorkeling, paddleboarding, and kayaking. Stroll to Siesta Key Village for shopping, dining, and nightlife, or hop the free trolley or rent a golf cart. brbrBook Aruba by Siesta Key Luxury Rental Properties for a private pool Siesta Key vacation, sunny beach days, easy access to Siesta Key Village, and comfortable coastal living await. Reserve your dates today.br brbr-brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis property has active video surveillance on the pool equipment only. brbr3 cars 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. 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. 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.

Bed

Bath

Sleeps

$1209.13

/ Nightly

Private Vacation Home

Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

Casa De Siesta | Private Heated Pool + Walk to Siesta Key Villagebrbr Why You'll Love This HomebrStep into tropical elegance just steps from the village. You'll enjoy sunlit interiors, a private heated pool & hot tub, and seamless indoor‑outdoor living designed for connection and rejuvenation.brbr ‍ ‍ Perfect ForbrFamily groups, multi‑gen travel, or couples seeking privacy with shared amenities.brbr ️ Imagine ThisbrWake up to golden light filtering through palms, hit the pool for a morning dip, then wander down the block to sip coffee at a café in Siesta Key Village. Midday, stretch out on the sand at Siesta Key Beach (a quick 0.3 mile stroll), then return for a BBQ by the pool. As evening falls, gather with friends in the hot tub, and enjoy the sunset. You'll feel relaxed, refreshed, and like you're exactly where you want to be.brbr Where You'll SleepbrVilla Fiesta:br• Bedroom 1: King Bed, Ensuite Full Bath, First Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, First Floor, TVbr• Living Room: Queen Sleeper SofabrbrVilla Margarita:br• Bedroom 3: King Bed, Ensuite Full Bath, Second Floor, TVbr• Bedroom 4: Queen Bed, Shared Bath, Second Floor, TVbr• Living Room: Queen Sleeper Sofabrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, Nightlifebrbr⌛ Don't wait—this home books quickly. Your reservation includes peace of mind with our CottageClean™ program: a 6‑hour deep clean and 35‑point inspection so you arrive to perfection.brbr Need to Know - This home is a combination of 2 units - Villa Fiesta - 312R and Villa Margarita - 314L that are accessed by different entrances and do not share common space indoors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pups stay just as wonderful as yours.

Bed

Bath

Sleeps

$611.32

/ Nightly

Private Vacation Home

Villa Fiesta | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

Villa Fiesta | Pet Friendly Home In Siesta Village, Shared Heated Pool and Hot Tub, Walk to the Beach!brbr Why You'll Love This HomebrLive like a local in the heart of Siesta Key Village, just a 5-minute walk to the island's world-famous beach. Villa Fiesta blends vibrant charm with relaxed coastal style—complete with a shared heated pool, dog-friendly policy, and the freedom to walk to everything. This colorful island retreat is made for morning strolls, beach days, and sunset BBQs.brbr ‍ ‍ Perfect ForbrSmall families, couples, or friend groups looking for a lively, walkable Siesta Key experience—plus one well-behaved pup (under 25 lbs) is welcome too!brbr ️ Imagine ThisbrThe village is alive with energy as you arrive—bike bells, café chatter, and the scent of coconut sunscreen in the air. You step inside Villa Fiesta and instantly feel at ease. The coastal-inspired living room invites you to kick off your flip-flops and stretch out on the sofa. Upstairs, sun-drenched bedrooms await, each designed for rest and recharge. After a lazy afternoon on Siesta Key's powder-white beach—just 0.3 miles away—you return to the shared backyard oasis. The grill sizzles, the hot tub bubbles, and laughter echoes as the sun dips below the palms. Every moment here feels light, bright, and unforgettable.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Full Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Full Bath, Third Floor, TVbr• Living Room: Queen Sleeper Sofa – Main Living Area, Half Bath Nearbybrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Fiesta places you in the perfect spot to enjoy it all.brbr⌛ Don't wait—Homes this close to Siesta Key Village go fast—lock in your stay now. Your reservation includes full access to our CottageClean™ program: a 6-hour deep clean and 35-point inspection that ensures a pristine, worry-free arrival.brbr NEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This home has stairs, if you or someone in your party has trouble with stairs, please contact us for more details. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours.

Bed

Bath

Sleeps

$593.02

/ Nightly

Private Vacation Home

Palm Island Estate: Mediterranean Luxury w/ Pool & Private Canal Access

Siesta Key, Florida, United States

Enjoy automatic discounts based on your stay length, no codes needed, and the price you see already includes your savingsbrbrWelcome to Palm Island Canal Estate! brbr brbrIndulge in the ultimate Siesta Key lifestyle at this breathtaking Spanish Mediterranean custom estate. Nestled in a prestigious, quiet enclave, this 3,500 sq. ft. masterpiece offers a rare combination of canal-front serenity and beachside convenience. Whether you’re launching a kayak from your private backyard or taking a 5-minute stroll to the powdery sands of Beach Access #10, this home is the pinnacle of coastal luxury. brbr brbrTHE OUTDOOR OASIS brbr- Private Splash Pool: Refresh in your heated pool (maintained at a perfect 86°F year-round at no extra cost). brbr- Canal-Side Living: Launch your kayaks directly from your backyard and explore the scenic waterways of Siesta Key. brbr- Outdoor Lounging: Multiple screened lanais and seating areas offer the perfect vantage point for morning coffee or sunset cocktails. brbr brbrDESIGNER INTERIORS brbr- Mediterranean Elegance: Custom architecture featuring dark cherry cabinetry, granite countertops, and soaring ceilings. brbr- Coastal Sophistication: Professionally decorated with Tommy Bahama-inspired furnishings and a dedicated wet bar for evening entertaining. brbr- Dining for the Whole Group: Features a formal dining room, a side café nook, and a convenient main-floor powder room for guests. brbr brbrHOME LAYOUT & BEDROOMS brbr- Suite Privacy: The 4-bedroom layout is spread across multiple levels, offering maximum privacy for large groups. brbr- Master Sanctuary (Upper Level): A King suite with private lanai access and a spa-like ensuite featuring a jetted tub and walk-in shower. brbr- King Guest Suite (Mid-Level): A spacious King room with a private ensuite bathroom. brbr- Additional Guest Rooms (Upper Level): One Queen bedroom with balcony access and one Twin bedroom - perfect for kids or extra guests. brbr- Remote Work Den: A dedicated workspace with a desk for those who need to stay connected. brbr brbrPROPERTY FEATURES brbr- Climate & Comfort: Central AC and ceiling fans throughout. brbr- Tech-Ready: Dedicated high-speed WiFi and YouTube TV included. brbr- Parking & Extras: Spacious garage/driveway parking and complimentary beach gear provided. brbr brbrIMPORTANT INFO brbr- Layout Note: This custom home features multiple staircases, which adds to the architectural charm but may not be suitable for those with limited mobility. brbr- Pristine Environment: Located in a quiet residential area. Strictly no pets, smoking, or parties. brbr brbrYOUR LUXURY BEACH VACATION STARTS THE MOMENT YOU RESERVE. BOOK PALM ISLAND ESTATE TODAY!brbrIMPORTANT: The min age to rent is 25 years old. No parties, large gatherings. Please reach out if you have any questions.

4

Bed

3

Bath

8

Sleeps

$208.11

/ Nightly

Private Vacation Home

1255-501 Bayside Retreat with Coastal Charm

Siesta Key, Florida, United States

Welcome to this beautifully remodeled Bayside Mid-rise unit. This spacious 2-bedroom, 2-bathroom condo is situated on the 5th floor, brbrAs you step inside, you'll be greeted by a tastefully decorated living area with modern furnishings and a serene coastal color palette. The open-concept design seamlessly connects the living, dining, and kitchen areas, creating a perfect space for relaxation and entertainment. The living room features comfortable seating, a flat-screen TV, and large sliding doors that lead to a private, enclosed balcony.brbrThe dining area, adjacent to the kitchen, is well-appointed with a stylish dining table that seats four, making it ideal for family meals or entertaining guests. The fully equipped kitchen boasts contemporary appliances, ample counter space, and all the essentials needed to prepare delicious meals.brbrThe master bedroom is a tranquil retreat, complete with a king-size bed, en suite bathroom, and plenty of storage space. The guest bedroom is equally inviting, offering a queen-sized bed and easy access to the second bathroom located in the hallway. brbrAdditional amenities include hardwood floors throughout, a full-size washer and dryer for your convenience, and a covered parking space. Guests will also have access to high-speed internet, beach access, tennis courts, exercise facilities, and two swimming pools.brbrThis unit is perfect for those seeking a luxurious and comfortable stay with all the conveniences of home. Please note that there is a 30-night minimum stay requirement, and pets are not permitted on the property.

Bed

Bath

Sleeps

$559.29

/ Nightly

Private Vacation Home

Sunnyside Up Cottage - Walk to Siesta Beach, Waterfront Home by Gulf Coast Holiday Homes

Siesta Key, Florida, United States

Welcome to your dream getaway on Siesta Key! This beautifully appointed, fully renoavted 3-bedroom, 3-bathroom waterfront home offers the perfect blend of comfort, luxury, and island living. Nestled on a quiet canal just minutes from the world-renowned Siesta Beach, this private retreat is ideal for families, couples, or boating enthusiasts. Pet Friendly - all pets must be approved by management. Pet Fee $250.brbrKey Features:br3 Spacious Bedrooms – Comfortably accommodates families, couples, or small groupsbrPet Friendly - All pets must be approved by management. Pet Fee $250.brPrivate Heated Pool – Soak up the sun or take a refreshing dip any time of yearbrCanal Access with Private Boat Dock – Bring your boat or rent one locally to explore Sarasota Bay and the GulfbrJust Minutes from Siesta Key Beach – Walk, bike, or drive to one of America’s top-rated beaches with powdery white sandbrFully Stocked with Beach Gear – Includes chairs, umbrellas, towels, and coolers for hassle-free beach daysbrGourmet Kitchen – Equipped with everything you need to prepare meals at homebrUnbeatable Siesta Key Location – Close to Siesta Village shops, restaurants, and the vibrant nightlife of downtown SarasotabrModern Comforts Throughout – High-speed Wi-Fi, smart TVs, laundry, and stylish furnishings for a relaxing staybrSpacious Outdoor Entertaining Area – Perfect for grilling, dining al fresco, or lounging by the pool with tropical viewsbrbrWelcome to Siesta Key, a sun-drenched barrier island on Florida’s Gulf Coast, known for its laid-back charm, vibrant beach village, and the world-famous Siesta Beach, consistently ranked among the best in the U.S. thanks to its soft, powdery white quartz sand.brbrWhether you're seeking a relaxing retreat or an adventure-filled escape, Siesta Key offers something for everyone. Spend your days swimming in crystal-clear turquoise waters, paddleboarding along gentle bays, or exploring the lush mangrove tunnels by kayak. In the evening, stroll through the lively Siesta Key Village, where you'll find open-air dining, boutique shopping, and live music under the stars.brbrWith easy access to downtown Sarasota, top-notch golf courses, art galleries, and nature preserves, Siesta Key is the perfect blend of tropical tranquility and cultural sophistication.brbrThis island paradise is a beloved destination for families, couples, and snowbirds alike—and once you visit, you’ll understand why guests return year after year.brbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you. brbrGulf Coast Holiday Homes offer a wide range of services including: br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations. br- 'Preferred Vendors' menaing you can trust the company you use for rentals.brbrAll properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrStep inside to discover an open-concept living area filled with natural light, coastal-inspired décor, and all the modern amenities you need. The fully equipped kitchen features quartez countertops, stainless steel appliances, and a breakfast bar, perfect for morning coffee or evening cocktails.brbrEach of the three spacious bedrooms offers a serene escape with plush bedding and en-suite or nearby bathrooms. The master suite includes direct access to the pool deck and a spa-like bathroom with walk-in shower.brbrOutdoors, your own private heated pool awaits, surrounded by tropical landscaping and a sun-soaked patio complete with lounge chairs and a BBQ grill. Just steps away, the private boat dock gives you direct access to the waterway, bring your boat or rent one nearby and explore Sarasota Bay or head out to the Gulf.brbrBeach chairs, towels, and bikes for your conveniencebrbrWhether you're relaxing by the pool, launching off for a day on the water, or strolling the charming shops and restaurants of Siesta Village, this exceptional home is your gateway to the ultimate Florida vacation.brbrProperty can be accessed via electronic door code, sent to allow guests on day of arrival. brbrDirections: Take I-75 South to Exit 205 for FL-72 W toward Sarasota. Continue on FL-72 W, which becomes Stickney Point Rd. Turn right onto Midnight Pass Rd, heading south. Turn left onto Avenida De Paradisio; the destination will be on your left just before the cul-de-sac.brbrParking is available on site for a maximum of 3 cars in the driveway. Parking is available on the street. The garage is not available to guests.brbrThis property must be rented for a minimum of 30 nights. If the travel dates you are looking for don’t appear to be available, please contact our reservations team directly and we will see if we can accommodate your request at your property of choice, or another comparable home in our portfolio.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrAccidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at Gulfcoast Holiday Homes. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71. brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.

Bed

Bath

Sleeps

$1258.02

/ Nightly

Private Vacation Home

Resort Style Backyard! Private Dock and Beach Views! - Sea Spray

Siesta Key, Florida, United States

Sea Spray by Siesta Key Luxury Rental PropertiesbrbrWelcome to Sea Spray! This eight-bedroom and six-and-a-half-bathroom home will check off all the boxes for your desired Siesta Key rental. It is a short walk to Siesta Key Beach and within walking distance to Downtown Siesta Key Village Area. So, catch some sunshine at the beach or enjoy great live music, dining, or shopping in the village. brbrHighlightsbr• Private Dock br• Rooftop Deckbr• Beach Viewsbr• Less than a 5-minute walk to the beachbr• Private Pool with Waterslide and In-ground Spabr• Ping Pongbr• Foosball tablebr• Convenient location near dining and shoppingbr• Dog friendly with approval and additional feebrbrThe spectacular backyard is built like a private waterpark with a Private Resort Style Heated Pool featuring a Rock Water Slide, Waterfall, Grotto, Swim-up bar, Sun Shelf, and Spa. You’ll love the lounge chairs, dining options, and BBQ grill. brbrJust across the street is your own private dock on the canal So, throw in a line and try your luck at fishing, or explore the bay by boat, kayaks, or paddleboards! brbrTake the elevator up to the main living floor, where you’ll find a lovely living area with plenty of seating for all your guests and large sliding doors leading to the furnished balcony; this is where you can access the rooftop deck. The kitchen highlights stainless steel appliances, cookware essentials, and two island seating options; the dining table and nook seating are adjacent, great for large parties. brbrThe game room is located just off the pool area with a ping pong table, a foosball table, and a refrigerator. brbrThe primary bedroom is a dream! It’s spacious with a walk-in closet, a private balcony with Adirondack chairs, an ensuite bathroom with a delightful baby blue double vanity, a large walk-in shower, and a premium standalone tub. The second/third bedroom has a unique setup with a King bed and a bunk bed with a curtain to separate the two, an ensuite bathroom with a walk-in shower, making it a perfect room for parents and kids! There are two King bedrooms with ensuite bathrooms and two King bedrooms that share a Jack-n-Jill bathroom with a walk-in shower. The last bedroom is the bunk room with easy access to the hall bath with a walk-in shower. The living room has a sleeper sofa and a laundry room on the second floor. brbrRoom Details br-Primary Bedroom, 3rd floor: King bed, private balcony, and ensuite bathroom with walk-in shower and standalone tub br-Second Bedroom, 3rd floor: King bed and shared ensuite bathroom with the third bedroom br-Third Bedroom, 3rd floor: Twin over Full Bunk Bed with a Twin Pull Out Trundle and shared ensuite bathroom with the second bedroom br-Fourth Bedroom, 3rd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower br-Fifth Bedroom, 2nd floor: King bed, balcony access, and an ensuite bathroom with a walk-in shower br-Sixth Bedroom, 2nd floor: King bed, balcony access, and Jack-n-Jill bathroom with walk-in shower br-Seventh Bedroom, 2nd floor: King bed and Jack-n-Jill bathroom with walk-in shower br-Eighth Bedroom, 2nd floor: Two Twin bunk beds and ensuite bathroom with walk-in shower brbrBook your dream vacation today! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 cars 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. 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.

Bed

Bath

Sleeps

$527.35

/ Nightly

Private Vacation Home

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!

Siesta Key, Florida, United States

Villa Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!brbr Why You'll Love This HomebrTucked above the lively village streets, Villa Margarita offers a breezy, light-filled retreat with elevated privacy, designer comfort, and shared access to a heated pool and spa—just 0.3 miles from world-famous Siesta Key Beach.brbr ‍ ‍ Perfect ForbrCouples, small families, or beach lovers craving a stylish escape with village convenience.brbr ️ Imagine ThisbrWake to a soft breeze drifting through upstairs windows. Get the day going by brewing coffee in the bright kitchen, step onto the balcony, and watch the village below slowly wake up. By late morning, you're walking to the beach—cooler packed, flip-flops on. After a sun-soaked afternoon, it's back to the villa to dip into the shared hot tub, grill fresh seafood, and toast to another unforgettable day on the Key.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Shared Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Second Floor, TVbr• Bonus Room: Queen Sleeper Sofa – Main Living Areabrbr Explore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Margarita places you in the perfect spot to enjoy it all.brbr⌛ Don't Wait - This sought-after upper unit fills fast—reserve now and travel worry-free with our CottageClean™ program: a 6-hour deep clean followed by a 35-point inspection before every stay.brbr NEED TO KNOW: This home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. We happily welcome one small dog (up to 25 lbs) with a $250 per week pet fee—breed guidelines apply to ensure a safe and comfortable stay for everyone. Please reach out prior to booking so we can help make your pup's stay just as wonderful as yours.

2

Bed

1

Bath

6

Sleeps

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