Vacation Rentals & Apartments in Naples

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4,164 apartments

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

Match: Boat available Washing machine Horse riding Smoking allowed Car not required

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Price per night from

$138

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Bahia Beach Resort Little Harbor-Tampa, FL

Tampa studio

  • Studio
  • 1 bathroom
  • sleeps 4

“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: Smoking allowed, Horse riding, Boat available, Washing machine, Car not required

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Price per night from

$138

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

4 of 5 match: Boat available, Horse riding, Washing machine, Smoking allowed, Car not required

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Price per night from

$149

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

4 of 5 match: Car not required, Horse riding, Boat available, Washing machine, Smoking allowed

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Price per night from

$157

Beautiful Barrier Island Beach House with Pool, Spa and Dock - Walk 2 Beach!

Don Pedro Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$597

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price 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

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$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

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$573

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$114

LUXURY UPDATED “BEACHFRONT”, Riviera Club Fort Myers Beach, SUNSET VIEWS!!!!!!!!

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$230

Quiet S.Tampa

Tampa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 42 minutes

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$149

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$201

Sea Club II - 1B: By Beachside Management

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$240

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$975

Pool Home - Steps from the Beach

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$1,147

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

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$975

Lattitude Adjustment- Private Beachfront Home with Fishing Dock, Sunrises

North Captiva Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$918

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

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$744

Key West Flair

Sanibel condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 5 match: Horse riding, Boat available, Washing machine, Smoking allowed, Car not required

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Price per night from

$311

BEACH BEAUTY

Fort Myers Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 53 minutes

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$258

Charming Siesta Key Village Unbeatable Location

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$190

Deluxe Queen Suite in Gorgeous Pop Art Gallery Pool Home Close to Everything!

St. Petersburg private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 5 match: Horse riding, Boat available, Washing machine, Smoking allowed, Car not required

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Price per night from

$144

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Horse riding, Boat available, Washing machine, Smoking allowed, Car not required

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Price per night from

$159

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$344

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: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$446

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$516

Beachfront Paradise w/ Private Beach, Dogs Stay Free, Beach in Backyard

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$631

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$745

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

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Price per night from

$122

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

3 of 5 filters match

Price per night from

$117

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

3 of 5 match: Boat available, Smoking allowed, Horse riding, Washing machine, Car not required

3 of 5 filters match

Price per night from

$2,293

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$488

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 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

3 of 5 filters match

Price per night from

$273

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$293

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 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$509

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!

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

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Price per night from

$643

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 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

3 of 5 filters match

Price per night from

$325

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.❤

3 of 5 match: Horse riding, Smoking allowed, Boat available, Washing machine, Car not required

3 of 5 filters match

Price per night from

$190

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