Condos Naples

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4,327 condos

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Bicycles available Boat available Car not required

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$911

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Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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$858

Cottage By The Water With Boat Dock

Tarpon Springs cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

“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 4 match: Rental types, Bicycles available, Boat available, Car not required

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$138

Pink Gulfside Cottage, 100 steps to beach, Pet OK, Restored Beach House

Clearwater house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$286

“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.

Responds fast! avg. 14 minutes

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$287

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 4 match: Rental types, Bicycles available, Boat available, Car not required

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$572

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

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$338

Old Palm Waterfront Vacation Rental Home

Sebastian house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Wonderful house in great location” What a wonderful, well equipped home in such a great location. Both in the house and surroundings there is so much room to sit, walk, run and explore! All our family met here, 3 couples and 17 month twin boys and it was ideal! The porch at the back was just perfect for everyone, a wonderful safe area for the boys to play and comfortable chairs for us all to relax without a mosquito in sight! Open living room and kitchen was easy to work in with a delightful dining room where we could eat in the evenings. Good size bedrooms and bathrooms, the master suite is incredible and huge! The house is very easy to baby proof also, we took a couple of extra safety gates to keep our little guys from getting into mischief! And I have to mention the peacocks, they just stroll around everywhere, surprised us once or twice, but are very friendly and amazing birds. The location is great, there is a huge Publix , Dunkin Donuts and plenty other stores close by. I think if you want a peaceful, relaxing weekend, week or long vacation this is the home to rent. Bill Clark, the owner, was there to meet us and show us round and was on hand if we had any questions. We really look forward to going back soon!

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Price per night from

$373

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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$1,946

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.

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$446

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

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$1,145

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$744

Stella Maris-Beachfront, Ultimate Privacy, Spectacular Shelling, Sunset Views!

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$974

Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises

North Captiva Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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$916

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Price per night from

$155

Jamaica Royal Villas - Villa 42; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$240

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Price per night from

$315

Island Beach cottage rental w/king+2bikes+smartTV

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 9 minutes

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Price per night from

$224

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“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!

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$272

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$292

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.

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$686

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.❤

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Price per night from

$189

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.

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Price per night from

$228

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“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.

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$509

Sunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes

St. Pete Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 9 minutes

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$332

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$297

Pink Dolphin Cottage 100 Steps to the Beach Sleeps 7, Pets Okay, Value

Clearwater cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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$331

Steps from Beach, Pets OK, Sleeps 6, Clearwater Beach. 2 Bedrooms

Clearwater apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$377

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Price per night from

$423

“Great cozy home away from home.” We stayed in the Orleans bungalo apartment on July 15-18. It felt like we were at home. The apartment had lots of character and charm. Loved sitting outside on the terrace watching the free entertainment across the street , was it called the ship wrecked bar? I especially loved beiing able to go to the back alley and washing clothes. (I hope it belonged to the cottages property, if not then oops!) We utilized the kitchen and the gas grill out back on the patio.Everything was great and this cottage had plenty of space for two families. We met my cousins from Texas in Flordia for a vaca. We drove from Oklahoma. The flat screens worked great. I have no complaints about this place. I just want to say to all you all snotty people leaving negative comments.... Quit complaining or find somewhere else to stay. What exactly do you think you are getting when you hear the word "cottages" it's not going to have a bell hop and a maid that cleans up your messes daily. Maybe some of you never lived in 100 year old homes and only used to a lavish lifestyle. Obviously you spent your time in doors. not us we were at the beach the majority of the day until almost 9pm every night. I enjoyed my stay there. It was a good 3 day stay for us despite the rainy weather. Yet we still had fun.

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$297

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.

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$423

WATERFRONT HOME "BOATERS DREAM" 2br/3ba Pets OK

Redington Shores house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Rental types, Bicycles available, Boat available, Car not required

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Price per night from

$255

Casa Mar - Unit 56: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$263

Crescent Arms; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$411

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$286

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$434

Crescent Condos; by Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$515

SEASHELLS CONDO A FEW STEPS TO THE BEACH, HEATED POOL AND A GREAT LOCATION

Cocoa Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, Rental types, Bicycles available, Car not required

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Price per night from

$229

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