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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Siesta Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Sunset Royale - 206- Close to Beach and Siesta Village
Siesta Key Condo
- 
4.8 Star Review
Tropical, laidback, and filled with island flair, this two-bedroom condominium enviably situated alongside the world-renowned sands of Siesta Beach. Located on the second level, the open floor plan boasts views of the Gulf, white sands, and magnificent sunsets. Enjoy morning coffee or pre dinner cocktails from the Sunroom. The master bedroom featur.......read more
2 Bedroom(s)
Sleeps 6
Condo
Pet-friendly condo a short walk from private beach & fishing dock on bay
Siesta Key Condo
Get your second wind at A Second Wind! Roomy, quiet and comfortable third-floor condo at beautiful Island Reef. Beach-to-bay complex on the peaceful side of Siesta Key with a pool view. Our private Gulf beach, pools and bay are not crowded at all. Two heated pools, tennis courts, pickleball and sauna. The private beach is just a five-minute walk ac.......read more
2 Bedroom(s)
Sleeps 4
Condo
New Listing on Siesta Key, Steps to Pool, WiFi/Cable, Outdoor Patio, Sunroom, Carport, King Master
Siesta Key Condo
New Listing in peaceful Polynesian Gardens where you can walk to Crescent Beach on Siesta Key! Just a 12 minute walk to sink your toes in the white powder quartz sands of Crescent Beach! Relax every evening sitting in a beach chair under an umbrella with a glass of wine (ok, plastic!) to watch an incredible Gulf of Mexico sunset!! You won’t be disa.......read more
2 Bedroom(s)
Sleeps 4
Condo
Welcome to Paradise! Pet Friendly! Walk to acclaimed Siesta Beach!
Siesta Key Private vacation home
**** APRIL IS THE BEST MONTH TO BE IN PARADISE !!! ****
Ahhh, welcome to Paradise — where sunny, warm weather embraces your soul. Snow, ice, rain, gray days got you down? Cheer up! Come and see why spring is the best time of year to be in Siesta Key, Florida. Enjoy this private 3 bedroom, 2 bath house on Palm Island, the h.......read more
3 Bedroom(s)
Sleeps 9
Private vacation home
Perfect Siesta Village Pool Home! Walk to the beach and hang out in the Village!
Siesta Key Private vacation home
- 4.8 Star Review
This Lovely, fully updated 3 bedroom property that holds 4 Adults and 2kids.Its also is a 3 bath canal home 1 block from Siesta Village! Tropical private pool setting just off the main living area and the grand Master Bedroom. Second Master suite with private bath including soaking tub. All bathrooms completely redone in 2015. Quiet street literall.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Aloha Kai - Unit 4-updated and by the pool!
Siesta Key Cottage
- 5.0 Star Review
Fully furnished villas offer living room, dining area, fully equipped kitchens, 1 bedroom/ 1 bathroom. Screened porch. Short walk to the beach or pool. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parki.......read more
Studio
Sleeps 4
Cottage
Paradise! Remodeled 2 bedroom 2 bathroom with incredible views
Siesta Key Condo
- 4.9 Star Review
This spacious large ground floor corner unit is just steps away from the pool, hot-tub, fishing pier and poolside BBQ\'s. One of the few units with an incredible direct view of the bay and pool. Voted the #1 beach in the USA, Crescent Beach, with it\'s beautiful quartz sand which looks and feels like powdered sugar, is just a short walk through t.......read more
2 Bedroom(s)
Sleeps 6
Condo
CA403N - 2/2 DIRECTLY ON THE BEACH - 4th Floor Views - Vacation Getaway
Siesta Key Condo
- 4.6 Star Review
403 N.
Last minute specials!
$200 off during the weeks of August 20/2022 to September 3/2022 and September 24 to October 1, 2022.
Come and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo.
We are located on the 4th-f.......read more
2 Bedroom(s)
Sleeps 6
Condo
Walk to Siesta Key Beach, Pool/Spa/Tiki Bar, WiFi, Close to Village Shops, Laundry
Siesta Key Private vacation home
- 4.5 Star Review
If you are looking for a private home on Siesta Key that\'s only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a great novel under an umbrella with a glass of white wi.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Siesta Key 2-Bedroom Apartment - Anchorage - Beautiful Views!
Siesta Key Condo
- 4.0 Star Review
Well appointed 2 bedroom, 2 bath condo at the corner of Midnight Pass and Stickney Point Roads. Private access to the beach just steps away.
Master bedroom features two Queen beds and adjoining bathroom with walk-in closet. Master bathroom recently renovated and upgraded. Second bedroom has two twin beds, two spacious closets and shared b.......read more
2 Bedroom(s)
Sleeps
Condo
New Listing! Sea Escape | Located in Siesta Key Village, Walk to the Beach!
Siesta Key Private vacation home
Welcome to Sea Escape! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.
Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key\'s world-renowned beaches are the .......read more
Studio
Sleeps 4
Private vacation home
- 106- Across from Siesta Key Beach with Fantastic Renovated Kitchen for large families!
Siesta Key Apartment
- 5.0 Star Review
Your ultimate vacation getaway, this two-bedroom condominium enviably situated across from Beach Access 11 at the world-renowned white sands of Siesta Beach. Located on the main level, the open floor plan boasts views of the Gulf, white sands, and magnificent sunsets. The fully equipped kitchen features granite counter tops and a large breakfast ba.......read more
2 Bedroom(s)
Sleeps 6
Apartment
Midnight Cove II - 137-bay views and Gulf access!
Siesta Key Condo
- 4.0 Star Review
Enjoy this beautiful condominium in Midnight Cove II! Watch the boats go by from your open 3rd floor Bay front balcony! Updated unit with new kitchen, newly upgraded master bath with walk in shower, and washer and dryer. Enjoy a game of tennis at of their nicely appointed tennis courts, or a dip in the pool at their invitingly large community pool.......read more
2 Bedroom(s)
Sleeps 5
Condo
Newly Renovated Large 4BR w/ Pool - Walk to Gated beach
Siesta Key Private vacation home
- 4.7 Star Review
Newly renovated gated beach access apartment with a pool. This is a four bedroom and two bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated section of the Siesta Key beach that only residents on this street have access too.
The house was completely updated and has all new furniture, .......read more
4 Bedroom(s)
Sleeps 12
Private vacation home
Tivoli by the Sea-Unit 502 - Beautiful unit with a beautiful view
Siesta Key Apartment
- 4.5 Star Review
Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!!! This unit sleeps 5 with a king in the master, a full and twin.......read more
2 Bedroom(s)
Sleeps 6
Apartment
Very Clean and fun ! Sarasota Siesta key beach Condo 1/1 2 +beds
Siesta Key Condo
- 4.3 Star Review
Beautiful, secure, upgraded unit with new curve TV, Live in Amazing Siesta Key, modern upgraded condo. Enjoy one of the nicest beaches in the world in style, our condo is located on beautiful Siesta Key, completely furnished, accommodations include an additional pull down murphy bed. This third floor unit is completely furnished with all you need t.......read more
Studio
Sleeps 4
Condo
Cozy Family Condo- Beautiful Newly Renovated 2 Bedroom - Near Siesta Key!
Siesta Key Condo
The Dock Holiday is located at the popular Bay Oaks Condominiums in a beautiful, park-like setting on the intracoastal waterway, where you can watch the sunrise. Spacious and updated, second floor, two-story condo with almost 1400 square feet of living space.
The living room is furnished with a large flat-screen TV, including free WiFi, and .......read more
2 Bedroom(s)
Sleeps 6
Condo
CA201N - SIESTA KEY–CENTER BEACH FRONT CONDO WITH SPECTACULAR VIEWS OF THE GULF
Siesta Key Condo
- 4.9 Star Review
201N.
Last minute specials!
$200 off during the weeks of August 20/2022 to September 3/2022 and September 24 to October 1, 2022.
Come and enjoy the sun and moon light on the Gulf and feel the powder white sands of Siesta Key between your toes, where the sand never gets hot, steps away from your condo.
We are located DIRECTLY O.......read more
2 Bedroom(s)
Sleeps 6
Condo
Chinaberry 456 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
- 5.0 Star Review
AMAZING views from this 5th floor 2BR/2BA condo overlooking the Beach and the Gulf! Brand New to our Rental Program! Spacious living, dining, lanai and kitchen, all with views of the water! King bed in master bedroom, full view of the water, with glass sliders out to the lanai. Very spacious master bath with large soaking tub (no shower.) Two twin .......read more
2 Bedroom(s)
Sleeps 6
Condo
"Safe & Clean" Hide-A-Way Suite, only 60 steps to the Siesta Key Public Beach
Siesta Key Apartment
- 4.7 Star Review
HIDE-A-WAY Suite
This enchanting comfortable and newly refurbished & updated 1 bedroom / 1 bath ground floor apartment, 580 is a strictly non-smoking unit. This apartment offers AC / heat, 1 king and a luxury queen size self inflating air bed for the living room.
All hyper-allergenic bedding, no feathers!
With a maximum occupancy of.......read more
Buttonwood 417 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
- 5.0 Star Review
**** 7 Night Minimum from Saturday to Saturday ONLY!**** Spacious 1600+ sq. ft. 3/2 ground floor unit. Step out lanai and back door to pool and beach! New flat screen tv\'s in living room and all bedrooms, king bed in master bedroom. Step-in shower/roman tub in master bath. Guest bedroom has queen bed and guest bath has a tub/shower combination. 3r.......read more
3 Bedroom(s)
Sleeps 6
Condo
NEW LISTING! Spend your winter in this condo just steps from Siesta Village!
Siesta Key Condo
Enjoy your stay on Siesta Key Beach!
Whispering Sands condo is located right on Siesta Key Beach and just a block from the Siesta Key Village, where you can enjoy countless restaurants, cafes, bars and boutiques.
Kitchen, Living Room and Master Bedroom all have beautiful views of the Gulf of Mexico. Master bedroom has a queen size .......read more
2 Bedroom(s)
Sleeps 4
Condo
Crystal Sands1107 Exquisite Gulf & Sand Views, Luxury
Siesta Key Condo
1107 is definitely a slice of heaven on Siesta Key. It\'s fresh and new with beautiful new beachy furnishings, new linens, and a full width view deck accessible from every room. Enjoy direct west and north views of the Gulf plus downtown Sarasota views. Take one of three elevators to sugar white quartzite sands & turquoise waters. Designer kitche.......read more
2 Bedroom(s)
Sleeps 6
Condo
Bright and Airy 4th floor condo at Fisherman's Haven with Private Beach and Stunning Water Views! FH
Siesta Key Condo
- 5.0 Star Review
Bright and Airy 4th floor condo at Fisherman\'s Haven with private beach and stunning water views!
Spacious, open-concept 2 bedroom featuring a roomy kitchen with breakfast bar, large bedrooms, and nicely furnished oversized living room with Bay views. King beds and large closets are provided in both bedrooms, and both have gorgeous views o.......read more
2 Bedroom(s)
Sleeps 4
Condo
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A
Siesta Key Condo
- 4.4 Star Review
Great Island Location - Walk to Beach, Shopping & Dining. Vista Hermosa 312A
Beautifully remodeled condo just completed in Dec. 2020. All new kitchen including counters, fixtures & appliances. New bathrooms with updated fixtures. New dining set, living room & bedroom furniture. New lanai furniture. New flooring throughout & freshly painted. .......read more
2 Bedroom(s)
Sleeps 6
Condo
New Listing - Bali Hai House - A Siesta Key Water Front Cottage
Siesta Key Private vacation home
- 5.0 Star Review
Everything you\'re looking for in a comfortable and convenient vacation is waiting for you at Bali Hai House! This gorgeous waterfront home is fully equipped with a spacious outdoor patio, fire pit, and private screened in heated pool. Hang out on the hammock and watch boats drift by or take a short walk to Siesta Key Beach. This spot is ideal for.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
1st Floor Gulf View, Convenient Walk Out to Pool w/ 3 Porches!
Siesta Key Condo
- 5.0 Star Review
Enjoy your beachfront vacation condo here in Siesta Key, with perfect sandy beaches right out your door. Siesta Key is a barrier island along the southwestern coast of Florida and is considered by beach experts to be one of the most beautiful beaches in Florida. When you stay with us at Siesta Dunes Condominiums, you stay in style and comfort, just.......read more
2 Bedroom(s)
Sleeps 5
Condo
Siesta Key Beach View Condo New Stainless Steel Kitchen Appliances
Siesta Key Condo
- 5.0 Star Review
Looking for a little get away at the Beach? Well, you’ve found it! This recently updated condo features two bedrooms and one full bath which puts you in the perfect location steps away from the world-famous quartz sand of Siesta Key Beach. There is no need to worry about parking, you are a one minute walk to the beach. This 4th floor condo has a co.......read more
2 Bedroom(s)
Sleeps 4
Condo
Buttonwood 472 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Siesta Key Condo
- 5.0 Star Review
Fabulously decorated 3/2 corner unit on the seventh floor. Wood flooring and ceramic tile throughout. The updated kitchen and baths adorn granite counter tops. Decorated with soft leather sofa and chairs, the living room comes with TV/VCR/DVD. Step out onto the screened lanai and feel the subtle tropical breeze. Experience the view of Crescent Beac.......read more
3 Bedroom(s)
Sleeps 6
Condo
Private villa, 7 min walk to beach, restaurants, grocery
Siesta Key Villa
- 4.9 Star Review
Amazing private location, steps away from all the action. Seven minute walk to beach, restaurants, grocery store, and boat rentals. This place will feel like your home away from home. Recently renovated with all new furnishings, including a large, fully stocked kitchen and 65-inch TV in living room. Enter this single family, one story, 1200 SF hous.......read more
2 Bedroom(s)
Sleeps 7
Villa
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Vacation Rentals Nearby Tampa Bay Destinations
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