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“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!
Match: Rental types Bicycles available Stereo system Swimming pool Car not required
All filters matchPrice per night from
$273
Deluxe Queen Suite in Gorgeous Pop Art Gallery Pool Home Close to Everything!
St. Petersburg private room
- 1 bedroom
- 1 bathroom
- sleeps 2
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
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$144
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$1,147
Stella Maris-Beachfront, Ultimate Privacy, Spectacular Shelling, Sunset Views!
North Captiva Island house
- 3 bedrooms
- 4 bathrooms
- sleeps 6
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$975
Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!
Anna Maria house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$744
4 of 5 match: Swimming pool, Rental types, Bicycles available, Stereo system, Car not required
4 of 5 filters matchPrice per night from
$458
“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$509
Family friendly condo on the beach - Ocean Sands
Madeira Beach apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$159
A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach
Siesta Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 9
“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$501
Tropical Escape Sarasota - Discover Real Florida Up-Close!
Lockwood Ridge house
- 3 bedrooms
- 2 bathrooms
- sleeps 12
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$149
BEACHSIDE BUNGALOW Lobster Shack *Htd Pool*Pets OK
Indian Shores cottage
- 1 bedroom
- 1 bathroom
- sleeps 4
“What a great getaway location to relax and view the secluded private beach and gorgeous ocean view!!!” We stayed in the Lobster Shack which is a cozy clean bungalow which offered a salt water pool with an awesome view of the Gulf waters. Liz is great making sure our needs were met while addressing unexpected refrigerator problems. She is quick to reply contacting a repairman to resolve the issue. Canines are welcome. I miss the relaxation and calmness of the setting yet on Gulf Blvd there are activities to meet everyone's interests. Thank you Liz and love your puppies.❤
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$189
Bocilla Island Club 2 Pools, boat dock, private 400 ft fishing pier
Bokeelia condo
- 2 bedrooms
- 3 bathrooms
- sleeps 6
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$218
BEACHFRONT BUNGALOW Marlin Hideaway *Htd Pool*Pets
Indian Shores house
- 2 bedrooms
- 1 bathroom
- sleeps 6
“Amazing!” Second time back and even better. Everything we needed to escape the craziness of COVID-19. Got to meet some new friends in the other bungalows and enjoy the beautiful beech! Can’t wait to return.
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$423
BEACHSIDE BUNGALOW Dolphin 2BR*HTD POOL*PETS OK
Indian Shores cottage
- 2 bedrooms
- 1 bathroom
- sleeps 6
“Thanksgiving Getaway” Beautiful location and our pet was able to come along. We enjoyed the beach, fire pit and weather. The one negative is that our unit was very close to a busy road.
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$228
EIKO BEACHFRONT HOME 4BR/3BA**HEATED POOL&SPA*PETS OK
Treasure Island house
- 4 bedrooms
- 3 bathrooms
- sleeps 13
“Water, water everywhere” So very, very close to the beach. Very helpful agent. Had 11 people with plenty of room .awesome time.
4 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$686
Beachside of the Village; By Beachside Management
Siesta Key townhouse
- 2 bedrooms
- 3 bathrooms
- sleeps 4
4 of 5 match: Stereo system, Rental types, Bicycles available, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$378
4 of 5 match: Stereo system, Rental types, Bicycles available, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$515
Clearwater Beach Waterfront - With Private Rooftop Terrace
Clearwater townhouse
- 3 bedrooms
- 3 bathrooms
- sleeps 6
4 of 5 match: Stereo system, Rental types, Bicycles available, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$402
2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach
Siesta Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.
3 of 5 match: Rental types, Swimming pool, Bicycles available, Stereo system, Car not required
3 of 5 filters matchPrice per night from
$316
Pink Gulfside Cottage, 100 steps to beach, Pet OK, Restored Beach House
Clearwater house
- 2 bedrooms
- 1 bathroom
- sleeps 5
3 of 5 match: Rental types, Swimming pool, Bicycles available, Stereo system, Car not required
3 of 5 filters matchPrice per night from
$286
“Awesome-perfect in every way” We cannot say enough possitive things about this home and the hosts. We have come to Tarpon for 30 years but this is the first time we ve used flipkey and we will only use flipkey from now on. From the welcoming hug to the perfect ammenities throughout, you could not beat this offering. Location is beautiful and perfect to access anything. The hosts were so nice and they had paid attention to so many details, we were overwhelmed. They had lots of suggestions and a great notebook filled with menus and things to do. Plus hints on specials, fishing and the area. As we ended our trip they even greeted us with a weather report--there was a storm headed our way. Thank you both for making sure this was the best time we ve ever had in this, our favorite, Florida location.
Responds fast! avg. 36 minutes
3 of 5 match: Rental types, Swimming pool, Bicycles available, Stereo system, Car not required
3 of 5 filters matchPrice per night from
$138
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$859
Jamaica Royal Villas - Villa 42; by Beachside Management
Siesta Key condo
- 1 bedroom
- 1 bathroom
- sleeps 2
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$240
Responds fast! avg. 1 hour 9 minutes
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$80
Fun Awaits at Luxurious Resort Condo: Fabulous Amenities, near Beach/Downtown!
Naples condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$315
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$412
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$263
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$320
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$515
Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome
Treasure Island condo
- 1 bedroom
- 1 bathroom
- sleeps 4
3 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$482
3 of 5 match: Rental types, Bicycles available, Stereo system, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$343
3 of 5 match: Rental types, Swimming pool, Bicycles available, Stereo system, Car not required
3 of 5 filters matchPrice per night from
$230
Clearwater Beach Hideaway Cottage, 3 bedrooms, Pets OK, Steps to the sand.
Clearwater cottage
- 3 bedrooms
- 1 bathroom
- sleeps 10
“Best weekend to the end of the summer” The hideawy cottage was perfect for what we needed peacefully, quite and dog friendly that what was the best part! The staff was great and professional and helpful. This was a perfect getaway for my birhtday celebration. I am turly coming back to take another mini vacation it was all the comfronts of home. I would like to thank the staff at Blue Wave Condo Suites for a wonderfully experience and this will be my new vacation spot when I travel back to Clearwater Beach.
3 of 5 match: Rental types, Swimming pool, Bicycles available, Stereo system, Car not required
3 of 5 filters matchPrice per night from
$446
Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip
North Captiva Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 10
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$573
Bianco Sands - 2 Bedroom - Poolside: By Beachside Management
Siesta Key villa
- 2 bedrooms
- 2 bathrooms
- sleeps 5
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$332
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$515
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$378
3 of 5 match: Rental types, Stereo system, Bicycles available, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$309