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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 Boat available Stove Swimming pool Car not required
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$273
Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!
Don Pedro Island house
- 3 bedrooms
- 4 bathrooms
- sleeps 7
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$597
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$859
Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches
North Captiva Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 7
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$1,147
Endless Summer - North Captiva Island 3 Bedroom 2.5 Bath, Sleeps 10 - Boat slip
North Captiva Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 10
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$573
“Perfect Vacation Relaxation Spot” The view from the room and balcony was gorgeous. Sitting on the balcony each morning sipping my coffee was heavenly. All of the amenities were close to the room and just short walks away. The property itself was well maintained and quiet while still being family friendly. The room was comfortable and a great home base at the end of our daily jaunts. Tampa, St. Petersburg, and Clearwater were very easy drives from the Inn. I can't wait to visit again.
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$138
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$1,147
Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises
North Captiva Island house
- 4 bedrooms
- 5 bathrooms
- sleeps 10
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$918
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, Boat available, Stove, 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, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$745
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$344
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$488
PRIVATE BEACH OPEN** Beachfront bungalow 4BR *Htd POOL*Pet
Indian Shores house
- 4 bedrooms
- 2 bathrooms
- sleeps 10
“A wonderful place to be!” Our rental was right on the pool/beach. It was perfect! Gorgeous pool and the beach - beautiful, private - everything you could want. The cottages were spacious, clean and kitschy. They had everything you needed. You could tell good people stayed there as everything was well kept and stocked. The owner, Liz, was lovely and even though we had no pets, every pup there was well behaved and everyone was respectful of the rules. The people staying at the other cottages were wonderful and had stayed there before. Obviously Liz knows what she’s doing . My parents also stayed with us and both of them loved the place. The beds were very comfortable which doesn’t always happen in rentals. Hoping to see you next year! Cheers!
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$488
“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, Boat available, Stove, Swimming pool, Car not required
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$510
Luxury Beach Front Villa with Pool, Captiva Island
Captiva Island house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
“Sunset Dreams - Tropical Paradise” What a wonderful place! We just returned and we miss it very much already. As my wife puts it, "it was like being in another world!" She's become an overnight ornithologist and marine biologist. The owners went well above the standard of what a normal property rental would be. From furnishings, to decor, to kitchen utensils, and appliances; they blow every rental property we've ever seen right out of the water. The home is immaculate. And the island itself has endless things to do. We've already booked for next year!
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$643
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, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$774
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, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$424
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, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$190
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, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$229
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$320
Tropical Bliss: Lazy River, 5 Pools, Bar, 2 Restaurants, Cabanas!
Naples condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
4 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$459
4 of 5 match: Boat available, Rental types, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$515
Beachside of the Village; By Beachside Management
Siesta Key townhouse
- 2 bedrooms
- 3 bathrooms
- sleeps 4
4 of 5 match: Boat available, Rental types, Stove, Swimming pool, Car not required
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$378
NSS Pattam, custom 84 foot traditional motor yacht downtown.
St. Petersburg yacht
- 3 bedrooms
- 3 bathrooms
- sleeps 6
Responds fast! avg. 1 hour 42 minutes
3 of 5 match: Rental types, Stove, Boat available, Swimming pool, Car not required
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$1,376
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, Boat available, Stove, Car not required
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$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, Boat available, Stove, Car not required
3 of 5 filters matchPrice per night from
$138
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, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$483
“Love the condo!” We are absolutely thrilled with the place. Your pictures don't do it justice. Because of past experience, we brought our pepper grinder and a few "specialty" utensils; however, you are so well equipped we could have left them all at home!! And we absolutely love your lanai. There is so much room out there. And plenty of seating too. We enjoyed a glass of wine outside tonight. Everything looks great. Spotlessly clean and beautifully decorated. We are both looking forward to some sun and warmth, some cycling and tennis. Thanks for the use of the bikes. And having extra rackets is great. You were right even the sofa bed is very comfortable. Your place is so convenient to everything. Just wanted to let you know we love your place!!
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$190
Clearwater Beach Waterfront - With Private Rooftop Terrace
Clearwater townhouse
- 3 bedrooms
- 3 bathrooms
- sleeps 6
4 of 5 match: Boat available, Rental types, Stove, Swimming pool, Car not required
4 of 5 filters matchPrice per night from
$476
“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$171
Naples 7min. to the beach - Play golf, tennis and pickle-ball 2 - WIFI
Naples apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 4
“Really nice, everything is new and immaculate.” The condo is perfect. It is immaculate, comfortable and pleasantly decorated. The owner made sure we had everything we needed, (well stocked kitchen, plenty of towels, laundry detergent etc.), for a wonderful vacation. The views from the balcony are beautiful and peaceful. The pool is just a few steps away from the condo where met very friendly residents.
Responds fast! avg. 1 hour 14 minutes
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$172
“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$430
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$458
“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$167
“Most Perfect Stay Anywhere” Everything was perfect. Host was most accommodating. Highly recommend to everyone for perfect stay. Beautifully appointed condo. Everything worked perfectly. Great pool for warm afternoons. Friendly neighbors. Close to everything. Highly recommend to anyone who wants a stay to remember.
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$96
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, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$316
Jamaica Royal Villas - Villa 42; by Beachside Management
Siesta Key condo
- 1 bedroom
- 1 bathroom
- sleeps 2
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
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$240
Responds fast! avg. 1 hour 9 minutes
3 of 5 match: Rental types, Boat available, Stove, Swimming pool, Car not required
3 of 5 filters matchPrice per night from
$84