Vacation Rentals By Owner In Siesta Key, FL

$484.92

Island House Beach Resort 15S

Siesta Key, Florida, United States

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, a guest bedroom offering two queen size beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

2

Bed

2

Bath

6

Sleeps

$293.1

/ Nightly

Private Vacation Home

Seaside Fun Awaits in This Bright & Breezy Coastal Escape - Aloha Kai #47 - Roelens

Siesta Key, Florida, United States

Aloha Kai #47brbrTime for Some Ocean Bliss!br brEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #47. This charming beach villa is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Fresh and inviting with colorful coastal comfort, Aloha Kai #47 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special: br brBedding Arrangement: br1 Bedroom: brMaster Suite: King-size bed and Smart TV brTop Features: brSleeps 2brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation. brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort. brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun. brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #47 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this villa offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #47 today and create memories that will last a lifetime! brbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future! brDISCLAIMERS: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.

Bed

Bath

Sleeps

$209.39

/ Nightly

Condo

Bay Oaks E-92

Siesta Key, Florida, United States

Summary:brbrCome relax in this quiet bayside complex that is surrounded by whispering oaks. 2nd floor unit is a 2 bedroom/2 bath remodeled unit. Complex offers tennis courts, community pool and pier for fishing. Unit has tile in main traffic areas with carpet in bedrooms. Leather sofa, open kitchen wit granite countertops. 3 LCD TVs and washer/dryer located inside unit. WIFI offered. Sleeps 6 (2 Queen, sleeper sofa). 1-week minimum.

Bed

Bath

Sleeps

$190.37

/ Nightly

Private Vacation Home

Everything is New! Immaculate Beach Front Condo with Stunning Views at Island Reef, 304A

Siesta Key, Florida, United States

The distance to the beach indicated on this website is incorrect. The condo is located ON the beach with a private beach area exclusively for Island Reef guests.brbrEverything is New in this Fabulous Beach Front condo with Stunning Gulf Views, Private Beach, 2 Heated Pools, Fitness Room, Tennis Courts and more!brbrImmaculate 3rd floor beach front condo overlooking the beautiful Gulf of Mexico! This condo has just been listed for rent and everything is new. Located in the desirable Island Reef complex on Siesta Key. This spacious condo features extraordinary views of the beach and sunsets from the front room, the lanai, the kitchen, and the master bedroom. Features a formal dining area and well-stocked kitchen with new appliances. Sleeps 4 comfortably with a king bed in the primary bedroom and a queen bed in the guest bedroom. Walk-in closet in the primary bedroom. Washer and dryer are in the unit, and free cable & WiFi are provided. Located at the quieter end of the island near Turtle Beach.brbrIsland Reef's Amenities include many social events, a private beach, tennis & pickleball courts, 2 heated swimming pools, fitness center, shuffle board, billiard and card rooms, barbeque areas, sauna, boat docks, kayak launch, and a large club house with kitchen facilities.brbrLocated just minutes from some of the area’s finest restaurants, shopping, golf courses, arts and entertainment. Hop on the Free Siesta Key Breeze Trolley and ride to Siesta Beach Pavilion and Siesta Key Village.brbrRENTAL POLICY: One month minimum is required.

Bed

Bath

Sleeps

$442.82

/ Nightly

Condo

Updated 2 Bedroom, 2 Bath Gulf View with 2 Lanais!

Siesta Key, Florida, United States

OCEAN VIEWS and ON THE BEACH!! This newly furnished and redecorated 3rd floor end unit, with 2 lanais, is perfectly situated, overlooking the Gulf of Mexico, the pool area, and of course Siesta Key’s incredible beach. Relax on the enclosed lanai or the end balcony with a glass of wine, a good book or just take in the spectacular ocean views as you enjoy the tropical breeze. Of course the perfect condo would not be complete without ocean views from the master bedroom as well. With 2 bedrooms (1 King & 1 Queen), 2 baths, a sofa sleeper and a fully equipped kitchen…just show up with your suitcase and enjoy all that Siesta Key has to offer.

2

Bed

2

Bath

4

Sleeps

$478.55

/ Nightly

Villa

Villa 20 - Premium Plus - Aloha Kai Vacation Villas

Siesta Key, Florida, United States

Escape to the beach and enjoy your own private slice of paradise in the beautifully renovated Villa 20 at Aloha Kai. This charming villa features an updated kitchen with granite countertops and a modern bath with a walk-in shower, offering both style and comfort. The inviting coastal décor creates a light, relaxing atmosphere throughout the space, making it the perfect retreat after a day in the sun. For added convenience, the villa also includes a washer and dryer. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family-friendly, gated resort community nestled in the heart of Crescent Beach—consistently ranked the number one beach in the continental United States. Renowned for its powdery white quartz sand and emerald-green waters, Siesta Key is one of Florida’s premier vacation destinations. The breathtaking three-mile stretch of Crescent Beach and the crystal-clear waters of the Gulf of Mexico offer the ideal backdrop for peaceful walks and unforgettable sunsets. Aloha Kai completes the experience with shaded beach pavilions and the largest pool on Siesta Key, creating the perfect setting for a laid-back, sun-soaked getaway.

Bed

Bath

Sleeps

$533.82

/ Nightly

Private Vacation Home

Fiesta Playa - Stunning Siesta Key Retreat

Siesta Key, Florida, United States

Welcome to Fiesta Playa, your perfect retreat on Siesta Key. This stunning 3-bedroom, 3-bathroom villa offers a luxurious escape for up to 8 guests. Upon entering, you'll be greeted by an open-concept living area with a fully equipped kitchen. The living room features a cozy sofa bed, ideal for additional guests. The villa is also conveniently located near popular attractions like the Siesta Key Village shops and restaurants, and the pristine Siesta Key Beach, perfect for swimming, snorkeling, and sunbathing. Whether you're looking for a family vacation, a romantic getaway, or an adventure-filled trip, Fiesta Playa offers the perfect blend of comfort, luxury, and convenience. Book your stay today and create unforgettable memories on the beautiful Siesta Key.br*This property is stairs only. All guests must have the ability to use stairs.brbrBedroom 1 – KingbrBedroom 2 – KingbrBedroom 3 – King brLiving 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

Bed

Bath

Sleeps

$484.92

/ Nightly

Apartment

Island House Beach Resort 15N

Siesta Key, Florida, United States

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, along with a guest bedroom offering two twin size beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key

Bed

Bath

Sleeps

$573.2

/ Nightly

Private Vacation Home

Coral Breeze | Pet Friendly Home, Heated Pool & Spa, Minutes to Village and Siesta Beach!

Siesta Key, Florida, United States

Coral Breeze | Private Pool + Walk to Siesta Key Villagebrbr Why You'll Love This Homebr Sunshine, swaying palms, and your own private pool—Coral Breeze offers the ideal island retreat just minutes from the heart of Siesta Key. With inviting indoor-outdoor living, lush tropical landscaping, and space for the whole family (including your pup!), this home sets the stage for effortless beach days and laid-back evenings.brbr ‍ ‍ Perfect Forbr Families, couples, or work-from-home guests seeking comfort, privacy, and easy access to Siesta Key Village and beaches.brbr ️ Imagine Thisbr Wake to the gentle glow of Florida sunshine as you sip coffee in the bright sunroom. The open-concept living area invites everyone to gather—whether you're whipping up breakfast in the fully equipped kitchen or planning your beach day. Step outside to your private backyard oasis, where the heated pool and hot tub are framed by tropical greenery. Spend afternoons soaking up the sun, dining al fresco under the covered patio, or grilling fresh seafood on the gas BBQ. When it's time to explore, Siesta Key Village is just a short stroll away, filled with boutiques, beachy cafes, and local flavor. After sunset, sink into crisp linens in your spacious bedrooms and drift off to sleep, dreaming of tomorrow's island adventures.brbr Where You'll Sleepbr - Bedroom 1: King bed, ensuite bathroom with walk-in shower, first floor, TVbr - Bedroom 2: Queen bed, shared hall bath, first floor, TVbr - Bedroom 3: Two full beds, shared hall bath, first floor, TVbrbr Explore the Areabr - 0.7 miles to Siesta Key Village – shopping, dining, and nightlifebr - 1.5 miles to Siesta Key Beach – world-famous white sand and turquoise watersbr - Easy access to mainland Sarasota for dining, arts, and entertainmentbrbr Don't Wait—Coral Breeze is a Guest Favorite!br Enjoy peace of mind with our CottageClean™ program: a professional 6-hour deep clean and 35-point inspection before every stay. Your Siesta Key escape starts here.brbr⚠️ Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. Free High-Speed WiFi. This pool is heated between November 15 - April 15 and comes equipped with a handrail for added convenience and ease of access. This property is registered as a vacation rental with the City of Sarasota with Registration Number VR2X-XXXXX. Due to City of Sarasota vacation rental code, this property must be rented once during a seven (7) day period and has a maximum occupancy of 8 guests.

3

Bed

2

Bath

8

Sleeps

$326.73

/ Nightly

Condo

Anchorage 610

Siesta Key, Florida, United States

We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAs you enter the condo, you are greeted by an open concept space which features cozy seating areas, ...TV and a dining room table. The openness of the floor plan allows for entertaining, family dinners and a sense of togetherness. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of palm trees swaying in the breeze (Siesta Key and the Gulf of Mexico). Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: 2 GASbrbr- Beach Access: PRIVATEbrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: QUEEN ONLYbrbr- Beds Pull-out: Yesbrbr- Elevator: 2brbr- Exercise Facility: Yesbrbr- Floor No.: KITCHEN TILE, CARPETbrbr- Internet Access: Yesbrbr- Parking: CARPORTbrbr- Parking Space Type: 38brbr- Electric Stove: Yesbrbr- View: BAYbrbr- PICKLEBALL: Yesbrbr- Bay View: BAYbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Bed

Bath

Sleeps

$765.02

/ Nightly

Private Vacation Home

Completely Renovated Beach House on Siesta

Siesta Key, Florida, United States

Welcome to island life! Enjoy your own private resort in the heart of the #1 beach in America, Siesta Key! brbrIndulge in the pinnacle of island living at this pristine waterfront home on Siesta Key—a haven where luxury meets natural beauty. In the heart of a picturesque landscape, nestled amidst lush greenery and framed by breathtaking views, lies this extraordinary property where luxury and nature's tranquility meet.brbrThis luxurious 3-bedroom, 2-bathroom retreat and additional detached ADU bedroom-is not just a home; it's your own private resort, seamlessly blending coastal elegance with the convenience of being within walking distance to the #1 Siesta Key Beach and the charming village. brbrCompletely updated February of 2025, the residence exudes coastal elegance with tasteful decor and high-end finishes. As you step into this luxurious retreat, you will be greeted by a spacious and open concept living room and kitchen, where beautiful views of the canal unfold before you. Almost everything in this home is brand new, including Sealy Posturepedic mattresses and Pottery Barn furniture—ensuring a level of comfort that exceeds expectations. brbrDrop your bags and say, Wow!brbrThe open concept living room and kitchen are bathed in natural light, creating a warm and inviting atmosphere. brbrThe well-appointed kitchen is a haven for culinary enthusiasts, featuring modern appliances and a layout that encourages socializing. A costal bar with drink fridge and ice maker are perfect for your morning coffee or evening cocktail. brbrThe 3-bedroom, 2-bath ranch-style layout offers privacy and convenience. br-The primary bedroom with a king bed boasts long views of the canal. Wake up in our heavenly bed to the beauty of the water and enjoy your morning coffee from the private dock. The luxurious en-suite bathroom and home office makes the primary bedroom a peaceful retreat. br- Two additional bedrooms offer serene retreats creating a soothing sanctuary for restful nights. One bedroom offers a luxurious king bed. The other bedroom has two queen beds. br- A detached Auxiliary Dwelling Unit with a full bed and office can function as the perfect workspace or teenager bungalow.brbrThe lush surroundings, featuring tropical palms, plants, and beautiful flowering landscape, create a magical setting—a true nature preserve for the soul. brbrYour private resort amenities include a heated pool, fire pit, and a private dock overlooking an endless canal. The focal point is the private dock, inviting you to explore the waterways or savor the breathtaking views. Fishing from your dock becomes a serene pastime, where you can witness dolphins, manatees, and pelicans enjoying the warm canal waters or boats passing by. The home is thoughtfully equipped with kayaks, allowing you to embark on water adventures right from your doorstep. Bring your own boat and tie it to our dock to explore all Siesta has to offer. Take a dip in the heated glistening pool. After a day of exploring the island beaches and sinking your toes into the powdery sand, enjoy the evening gathering around a cozy fire pit. This home is designed for ultimate relaxation and outdoor enjoyment.brbrLocated in the heart of Siesta Key, this home is perfectly positioned for easy access to multiple public beach access points and the dining and shopping delights of Siesta Key Village. The village at the end of our street offers a combination of family, brunch, sports bars, and fancy restaurants. Also lots of shopping at the end of the street which includes Lily Pulitzer, Southern Tide, Tommy Bahama and souvenir shops like Beach Bazaar and Alvin’s Island. Also, the Siesta Key market, liquor store, ice cream shops, and so much more are at the end of the street. Leave the car behind and explore the island using the provided bikes. Biking is a convenient way to explore the island effortlessly. The village is less than a 10-minute walk, and all beach access points are within a 15-minute stroll.brbrThis hidden gem invites you to escape to your own private island paradise—an easy-living retreat that combines luxury, privacy, and the natural beauty of Siesta Key. Indulge in the privacy and comfort of an unparalleled family getaway. Whether gathering on the dock for evening drinks or exploring Siesta Key Village's vibrant dining and shopping, this home's location offers the perfect balance of tranquility and entertainment. This classic Florida home offers a private dock, heated pool, bikes and kayaks at your disposal, every day becomes an opportunity for coastal adventures. brbrBook your stay today and experience the enchantment of this coastal sanctuary. Your private island paradise awaits—enjoy coastal lifestyle at its finest.brbrAdditionally, we would like to highlight our pool amenities for your enjoyment: The pool is heated from November 1st to April 1st, to a comfortable 85 degrees, providing a delightful experience during the cooler months. brbrCanal Access,brPrivate dock,brHeated Private Pool, brFire Pit,br4 Kayaks (2 single, 2 tandem)br4 Adult/3 kid bikes,br2 Car Garage,brDetached Air Conditioned Office,brAdditional Parking for up to 4 vehicles and 30 foot boat trailer or rv.brbrGetting aroundbrStay on the key and save yourself the headaches of traffic, bridge crossing, and parking. Walk, ride our bike, or rent a golf cart and enjoy island vacation mode your entire stay. brbrNo car needed but you are welcome to park four cars in the driveway during your stay.brbrWALKING-To reach the beach and town, just start walking west down Avenida de Mayo. The town is only .04 mile. Beach access points 2-8 are all less than .08 mile.brTROLLEY- The Siesta Key trolly picks up at the end of our street in front of Morton's Market. The Siesta Key Breeze Trolley is free for all riders. Additionally, it operates seven days a week making getting around convenient. The Trolley route follows Ocean Boulevard to Beach Road and down Midnight Pass Road. Trolley hours: Daily 8 a.m. to 10 p.m. Download the Trolley app.brBICYCLES-We provide a family set of bicycles during your stay. Please use the bike locks provided when leaving the bikes unattended in town or at the beach.brAIRPORT-There are several ride share options for easy access to nearby airports. Sarasota (20 minutes), Punta Gorda (58 minutes), St. Pete (1 hour and 15 minutes), and Tampa (1 hour and 15 minutes) airports are all with in an hour or so of the house.

Bed

Bath

Sleeps

$482.3

/ Nightly

Apartment

Gertrude's Siesta | Oceanview Penthouse | 1 min walk to Beach Path + Huge Terrace

Siesta Key, Florida, United States

Now available New Years (had cancellation)...Penthouse AqualinabrOcean view luxury penthouse. Breathtaking views from private 400sqft terrace! 20 steps from grounds to Americas best beach. Impeccably and fully renovated in 2023. 4-minute golf cart or free trolley ride to shopping dining and entertainment in Siesta Key Village. Travelers agree, this is the top ocean-view rental on Siesta Key! Book an escape today! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Breathtaking Ocean and Siesta Key Beach Views - from every room except the laundry and bathbr∙ Beachside - located only 20 steps from grounds to Siesta Key's award-winning beachesbr∙ The Terrace - 400sqft private terrace open airy, high above everything belowbr∙ Sunsets - walk 1-min to beach or watch the world's best sunsets from the terracebr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - 3-min free trolley ride to Village and live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ Activities - bikes, paddleboards, scooter and golf cart rentals nearbybr∙ Island Trolleys - stops right out front, free of charge to all Siesta Key pointsbr∙ Memories - walk to all the island's top attractions and guaranteed fun for allbrbrThe BeachbrOur beach has a quieter beach in front and to the right plus a lively popular crowd 50 yards south. It is a top spot on Siesta Key for sunsets and on Sundays the world-famous Siesta Key Drum Circle happens 100 yards down the beach. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. brbrThe HomebrLarge 1BR home 1000 square feet and fully remodeled in 2023. Beautiful décor and thoughtful amenities throughout. Its level is unmatched on Siesta Key. Set on the Southern edge of Siesta Village. Just 30 steps to top beaches, and 3-minute golf cart or trolly ride (15-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island. brbrBedroom DetailsbrThis ocean view property it's on the 4th floor with an elevator. There is one large king bedroom, and a queen sleeper in the living room. Some say the views in the living room make it the best sleeping area in the apartment. You can sleep up to 4 family style. brbrBeach Gear ProvidedbrWe provide beach towels, chairs, and umbrellas. 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.

Bed

Bath

Sleeps

$327.77

/ Nightly

Condo

Updated and clean, two heated pool, tennis, and beach access

Siesta Key, Florida, United States

Enjoy this updated townhome within walking distance to Siesta Key's main beach. The property is located within a resort style gated community offering two heated swimming pools, tennis courts, fitness room, gas BBQ grills, and fishing dock. All this nestled among lush tropical landscape and lakes. brbrArrive by car and utilize the garage or driveway for parking. Taking the stairs up to the second floor of the townhome, you enter through the front door into the home. Right away you will notice the updated eat-in style kitchen equipped with stove, fridge, microwave, and dishwasher. The kitchen also offers a breakfast bar opening out to the main living area. The living area is spacious and furnished with comfortable lounge seating for family and guests enjoying the 55 flat screen smart TV with HD programming and streaming services available. Just off the living area is the screened balcony overlooking a serine water feature and lake. The patio is furnished with outdoor dining set with seating for 6. Back inside you will also find the master suite on the main living floor. The master bedroom is furnished with king-size bed and TV. The ensuite bathroom features a shower and dual sink vanity. brbrFollow the stairs from the living room up to the loft area along with two additional guest bedrooms which share a bathroom. The one guest bedroom is furnished with queen-size bedroom set and TV while the other is furnished with a double and a twin with twin trundle and TV. brbrMinimum Stay Requirements: 1 week minimum Saturday to Saturday.

Bed

Bath

Sleeps

$239.84

/ Nightly

Condo

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Siesta Key, Florida, United States

There's nothing more refreshing than knowing you get to spend time in sunny Siesta Key. When you have a trip on the calendar and can't wait to make the most of every moment, booking your stay in Beach Road-Tropea is a must! This 1-bed, 1-bath abode is ideal for welcoming up to 4 guests at a time. That means that whether you're in town on an independent adventure, traveling with a significant other or enjoying a small group getaway, Beach Road-Tropea promises to be a home away from home that pairs comfort with the quality and convenience you deserve.brbrEmbrace a Prime LocationbrbrMaximizing the fun in Siesta Key comes down to booking a stay that keeps you close to the heart of it all. Beach Road-Tropea does that flawlessly simply by offering guests a great destination to enjoy! This property is located right across the street from Siesta Key Beach. That means that when you want to spend time soaking up the sun, you never have to go far to do so. Just a mile down the road from the front door, guests can enjoy time exploring Siesta Key Village which is packed with options in the way of restaurants, shops, bars, and nightlife venues! Around the corner, visitors can hop on the Siesta Key Trolley which is a charming and no-cost way to access the many landmarks Siesta Key hosts.brbrInterior Amenities to Enjoy brbrSpace, fresh island style and a touch of luxury too are yours for the enjoying when you book a stay in Beach Road-Tropea. This abode enjoys a spacious open design complete with large windows and a collection of tasteful furnishings to be found throughout. The living room hosts a turquoise sofa topped with colorful throw pillows which is settled in front of a glass-topped coffee table and large flat-screen television. brbrThe living room opens up to the dining room where guests can easily gather around the table for 4 when it's time to enjoy a meal together. Looking for more seating options It's easily found at the extended breakfast bar that adorns the large kitchen in this home away from home. The inspired culinary spaces also feature stainless steel appliances, ample cabinetry, and a decorative tile backsplash in stone gray.brbrGetting a good night's rest is easy to do in this property thanks to the fact that the bedroom hosts a king bed topped with a Casper mattress. Additional guest 3 and 4 will also enjoy a good nights sleep on the queen-size Murphy bed with Casper mattress. A large walk-in closet offers plenty of storage for your travel belongings. The units bathroom offers a shower and vanity. Beach Road - Tropea includes access to an outdoor shower for rinsing off coming back from the beach as well as an in-unit washer and dryer. brbrBook TodaybrbrWhen your Siesta Key adventure is calling, Rent Siesta Key is here to help. Reach out today to learn more about booking a stay in Beach Road-Tropea the next time you're in town!brbrPARKING: There is only room for 1 vehicle for this unit.

Bed

Bath

Sleeps

$599.89

/ Nightly

Private Vacation Home

Spacious Siesta Key Canal Front w/ Large Heated Pool

Siesta Key, Florida, United States

Take a look at this spacious canal front home on Siesta Key with heated pool. This home is great for a large family or even two families with its open floor plan. Enter the home through the double French doors and down the foyer into the heart of the home; the open family room, living room w/ fireplace, and eat-in kitchen. Large sliding glass doors run the entire length of the home looking out over the pool, backyard, and canal. The master bedroom offers a king-size bed and flat screen TV with on-suite master bathroom with Jacuzzi tub and 2-person shower. The second largest bedroom offers 2 queen beds and flat screen TV. The third bedroom is furnished with a California king bed and flat screen TV. These two bedrooms share a bathroom with tub/shower combo. The fourth bedroom is also furnished with a queen bed and flat screen TV. The family room has plenty of seating to take in the views or watch your favorite movies and shows in HD on the 50” flat screen TV. brbrStep outside to the pool deck where you can soak in the sun. There is also a fully screened in and covered part of the patio for the not so sunny days. The dock offers boat and Jet Ski lifts if you decide to rent some or if you are bringing your own.brbrMINIMUM STAY REQUIREMENTS: One month minimum with the exception of 2 week reservations a maximum of 30-days in advance.brbrOptional Fees:brbrPool Heating: $175/weekbrbrPets: $200 Non-refundable fee and prior approval required.

Bed

Bath

Sleeps

$253.31

/ Nightly

Condo

Spacious vacation rental condo with lagoon views, beach access, and pool

Siesta Key, Florida, United States

When you're overdue for a refreshing vacation, a trip to Siesta Key is always a good idea. Making the experience even more exciting is the choice to book a stay in Midnight Cove II - Doveplum. This welcoming 3-bed, 2.5-bath condo can easily accommodate up to 6 guests at a time and provide proximity to area fun while also incorporating the comfort, style, and convenience every traveler deserves! Integrated into a complex that sits next to a lush lagoon, guests will find that whether they're visiting with family or friends, a stay here offers up the scenery and style that they crave. brbrInterior AmenitiesbrbrWhen two-story living is just your style, Midnight Cove II - Doveplum is sure to please. This home away from home is spacious and bright, offering up an open floor plan for guests to enjoy that's designed to include large windows throughout. These features both frame the view and allow natural light to flood the condo during the sunny Florida daytime hours. brbrThe living room in this rental features a plush wrap around leather sectional sofa and matching armchair. Both are settled around a sleek glass coffee table and in front of a large flat-screen television. Dark finishes sit in beautiful contrast to the fresh white color palette featured throughout the main level of the condo. Floor-to-ceiling windows in the living room provide plenty of light to enjoy as well as an unobstructed view over the lagoon.brbrThe living room opens to the dining area and kitchen where guests can serve up a home-style meal when they choose to. The kitchen features a convenient breakfast bar, modern appliances and cabinetry already stocked with cookware as an added convenience. When it's time to dine, guests can gather at the table for six with ease. brbrGetting a good night's sleep is a breeze in Midnight Cove II - Doveplum. Each bedroom in this property hosts a plush mattress topped with high-quality linens and comforters as well as a television.brbrExterior FeaturesbrbrWhile exploring your surroundings is sure to inspire, this property has plenty of outside fun to enjoy right on-site as well. Guests will love that this condo has its own boat dock as well as private beach access just across the street when you want to access Siesta Beach or Crescent Beach. Looking for even more in the way of fun Make the most of the resort's tennis courts, BBQ area, and outdoor heated pool. brbrBook TodaybrbrEnjoying your Siesta Key adventure is easy when you have property professionals on your side to get you settled into style. Reach out to Rent Siesta Key today to learn more about booking Midnight Cove II - Doveplum the next time you're in town!brbrMINIMUM STAY REQUIREMENTS: 1 week minimum stay required. High season requires a Saturday - Saturday reservation.

Bed

Bath

Sleeps

$216.03

/ Nightly

Condo

Beachfront Sarasota Resort Condo: Siesta Key View!

Siesta Key, Florida, United States

Sink your toes into Siesta Key's white sand beaches and swim in the crystal clear waters of the Gulf of Mexico during your stay at this 2-bedroom, 2-bathroom Sarasota vacation rental condo! This 1,435-square-foot condo is located on Crescent Beach and comfortably accommodates 6 guests for a memorable seaside getaway. Situated in the Gulf and Bay Club Condominiums, this beachfront condo features fabulous on-site amenities including a secluded beach, 3 heated pools, a hot tub, and more.brbr-- THE PROPERTY --brbrOutdoor Dining Area | Direct Beach Access | Free WiFibrbrBedroom 1: King Bed | Bedroom 2: 2 Twin Beds | Living Room: Sleeper SofabrbrCONDO HIGHLIGHTS: Flat-screen cable TV, DVD player, dining table, en-suite bathroom, private screened patio brKITCHEN: Stove/oven, drip coffee maker, Keurig single-serve coffee maker, toaster oven, toaster, blender, dishware/flatware, refrigerator, dishwasher, breakfast tablebrGENERAL: Washer/dryer, linens/towels, complimentary toiletries, central air conditioning/heating, hair dryer, laundry detergent, iron/boardbrFAQ: Step-free accessbrPARKING: Designated parking (1 vehicle)brbr-- THE LOCATION --brbrSAND & SURF: Siesta Beach Access (on-site), Siesta Key Drum Circle (0.6 miles), Crescent Beach (0.9 miles), Sarasota Beach (1 mile), Point of Rocks (2 miles)brTEE TIME: Tournament Players Club (6 miles), Village Green Golf Club (7 miles), Stoneybrook Golf and Country Club (7 miles), Serenoa Golf Club (10 miles)brHIT THE TRAILS: Phillippi Estate Park (3 miles), Red Bug Slough Preserve (5 miles), Stoneybrook Nature Trail (6 miles), Marie Selby Botanical Gardens (6 miles)brAIRPORTS: Sarasota-Bradenton International Airport (11 miles), Tampa International Airport (72 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- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-in

Bed

Bath

Sleeps

$332.93

/ Nightly

Private Vacation Home

Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool

Siesta Key, Florida, United States

Spending time in sunny Siesta Key is always a treat for travelers. Those looking to enhance their stay with the inclusion of amazing accommodations will find everything they're looking for and more in Siesta Heron 7 / Heron House! This welcoming 3-bed, 2-bath retreat can welcome up to 10-guests at a time making it a wonderful choice for those traveling with family or friends alike. The property sits just a mile from Turtle Beach and no more than 3 miles from Siesta Key Beach. The restaurants, shops, and fun waiting in Siesta Key Village take only 4 miles to reach from the front door of Siesta Heron 7. Whether you're looking to cozy up in style or get out and discover something new, Siesta Heron 7 is the home away from home for you.brbrInterior AmenitiesbrbrMake the most of space, light, and welcoming style when you book a stay in Siesta Heron 7. This spacious retreat is designed with open living in mind and pairs up a layout with large windows throughout as well. These fantastic features frame a great view while also promoting maximum light flow during the daytime hours. The result is a bright and airy space for guests to call their own during a stay. brbrThe living room in Siesta Heron 7 features a leather sofa topped with colorful throw pillows situated behind a coffee table. The living room in this home also enjoys the inclusion of a large flat-screen television for added entertainment value to every stay. Sleek flooring runs across the living room as well as the dining area and kitchen. The culinary space in this home is ideal for those looking to serve up a home-style meal or two during their visit. The kitchen showcases black granite countertops and stainless-steel appliances as well as custom white cabinetry filled with cookware. The decorative backsplash brings in earth tones to match the flooring while the breakfast bar offers ample prep and serving area. brbrWhen it's time to rest, guests will find the bedrooms in this home inviting and restorative. The master suite hosts a king bedroom set complete with an en suite bath that hosts a shower. The first guest room features two queen beds that are ideal for those traveling with little ones in tow. The third bedroom offers up a pool view and also hosts two twin beds. Traveling with extended family or friends the living room space also provides sleeping accommodations via a queen-size Murphy bed. brbrExterior Features to EnjoybrbrGuests who book Siesta Heron 7 will find that fresh air and fun are always within reach. This property hosts a sprawling deck complete with a table and chairs for those moments when an alfresco meal would hit the spot. Reserving a place in Siesta Heron 7 also gives guests access to fun community features like the large, heated swimming pool and gas grilling area. The pool deck is adorned with a collection of sun loungers to enjoy when working on that Florida tan is a top priority!brbrBook Your Getaway TodaybrbrEnjoy every moment of your Siesta Key adventure and let Rent Siesta Key handle the accommodations while you're here. Reach out today to learn more about booking Siesta Heron 7 for your next visit!brbrOptional:brElectric vehicle charging station available, provided by ChargePoint.

Bed

Bath

Sleeps

$270.75

/ Nightly

Condo

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

Siesta Key, Florida, United States

The last of our Siesta Heron escapes offers something extra the others don't and that is an extra bedroom. Key Lime, the fifth unit in this tranquil community is a 2-bedroom, 2-bathroom unit with room for 6 guests to cohabitate happily. Offering a private screened-in patio, it is a popular choice for travelers with slightly larger families.brbrA sofa provides a comfortable place to read and relax on a lazy vacation day and the small table and chairs on the screened-in patio of Key Lime is an ideal spot to enjoy morning coffee or a sunset dinner. Open the door and walk inside where an open concept floor plan harbors no secrets. The living area with its wood-like tile floor and comfortable leather sofa faces a large flat screen television.brbrThe dining area tucked away in the corner of Sand Dollar is where games will be played, meals will be devoured, and adventure planning sessions will be held under the light of the lamp hanging over the table. Reminders of the herons that make Heron Lagoon their home adorn the walls of this space in the form of bright and colorful paintings that realistically depict their peaceful natures and serene beauty.brbrGranite countertops, stainless steel appliances, and custom cabinets painted a crisp white give the kitchen a modern appeal, while the shabby chic backsplash softening the space and adding a beachside cottage feel. As in the other Siesta Heron units a Keurig coffee maker allows coffee, tea, or even cocoa drinkers to start out each day the way they love best. brbrKey Lime provides a beautiful master suite, offering a queen bed topped comforter. The bath is an updated room, featuring a wide granite topped single vanity and a walk in shower backed with tiles that resemble wood flooring.brbrBedroom number two is also furnished with a king sized bed for additional guests to utilize. Occupants can pull the blinds closed before drifting off to dreamland and sleep in as late as they want, but there is so much to do on Siesta Key we think getting up with the sun may be a good idea after all!brbrMinimizing the possibility of morning traffic jams when six people are staying under the roof of Key Lime, the second bath features a tub shower combo and another wide and spacious single vanity topped with granite. White cabinets and a dark framed mirror give the space a modern appeal.brbrIf even more sleeping is needed, there is an air mattress that can be setup for you in the living room for those additional house guests. brbrAs with all of our Siesta Heron units, it is the outside spaces that will thrill and delight. A community pool that is heated in the winter months, grills placed strategically throughout the property, and a large deck that looks over the tranquil waters of Heron Lagoon are just a few of the amenities you will find in this quiet community. Beach cruisers and beach gear make beach days that much more fun and a coin laundry, although not glamorous or exciting, can be a life saver when traveling with kids who can't help but make messes everywhere they go!brbrOptional:brbrElectric vehicle charging station available, provided by ChargePoint.

Bed

Bath

Sleeps

$222.49

/ Nightly

Condo

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

Siesta Key, Florida, United States

The Siesta Heron Suites & Villas enjoys a proximity that is close to the heart of everything that makes Siesta Key special, and our Sand Dollar unit is another ideal example. One bedroom, one bathroom, and a spacious and open living area allows up to four guests to live together in comfort and harmony. Spend your days exploring the beauty of Siesta Key and the mainland areas of nearby Sarasota and Bradenton, located just over the bridge, and spend your night in the welcoming rooms of Sand Dollar, enjoying a vacation that reflects the beauty of Florida in every way.brbrA paver walkway leads to a patio just outside the front door of Sand Dollar, and as with the other units on this property, a small table and chairs offer the perfect way to enjoy your morning tea or coffee. Once inside, the laidback vibe welcomes guests, providing a living area in the open concept floor plan anchored by a comfortable sofa placed opposite a flat screen television. brbrSeating at the breakfast bar in the bright and cheerful kitchen gives meal time an intimate feel that will draw honeymooners closer together, and modern appliances continue to help encourage the closeness as dinners are prepared shoulder to shoulder. A coffee maker allows guests to start every day well caffeinated, and because it is a Keurig, tea drinkers and cocoa drinkers can purchase their favorite beverages and start out the day on the right foot as well.brbrThe bedroom is a large space, offering up a romantic ambience and a neutral décor that encourages a deep sleep, while bright accent colors help along happy dreams. The king bed is cloud soft and a ceiling fan keeps the room cool as it circulates the air on a warm summer day.brbrThe bathroom of Sand Dollar is a quiet room, offering updated fixtures and a vanity that will hold all the lotions and potions that make your bride feel beautiful. Fluffy white towels feel soft against sunburned skin because our attention to detail means we understand the aches and pains associated with too much sun.brbrAnd finally, we come to the amenity section of our tour of Sand Dollar. The community offers a quiet magic that will enhance your Siesta Key vacation and includes a community swimming pool, barbecue grills, and a deck that overlooks Heron Lagoon. The beaches of Siesta Key are in close proximity with Turtle Beach being the closest at only a mile away and the shops and restaurants that make our Florida island special are all within a 10 minute drive. brbrOptional:brElectric vehicle charging station available, provided by ChargePoint.brbrSleeping arrangements for guests 3 and 4 are twin-size roll-a-way beds available upon request.

1

Bed

1

Bath

4

Sleeps

Vacation Rentals By Owner In Siesta Key, FL

$484.92

$293.1

$209.39

$190.37

$442.82

$478.55

$533.82

$484.92

$573.2

$326.73

$765.02

$482.3

$327.77

$239.84

$599.89

$253.31

$216.03

$332.93

$270.75

$222.49

Rent a place that suits your needs

Most popular vacation rentals in Siesta Key

$2522.03

$2135.02

$2157.13

$2193.20

$2342.88

$2445.50

$2479.18

$3229.57

$3133.33

$3110.58

Most Popular Cities in Florida