Vacation Rentals & Apartments in Naples

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4,533 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: Garden Boat available Washing machine Horse riding 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: Garden, Horse riding, Boat available, Washing machine, Car not required

4 of 5 filters match

Price per night from

$138

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, Garden, 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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$860

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$1,148

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, Garden, Boat available, Washing machine, Car not required

3 of 5 filters match

Price per night from

$573

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$976

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$745

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$976

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$918

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, Garden, Horse riding, Washing machine, Car not required

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Price per night from

$517

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, Garden, Horse riding, Washing machine, Car not required

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Price per night from

$631

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, Garden, Horse riding, Washing machine, Car not required

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Price per night from

$122

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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

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Price per night from

$2,295

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$273

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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

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Price per night from

$510

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$488

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

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Price per night from

$688

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

Redington Shores house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$255

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, Garden, Boat available, Washing machine, Car not required

3 of 5 filters match

Price per night from

$332

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

3 of 5 filters match

Price per night from

$424

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

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

3 of 5 filters match

Price per night from

$224

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, Garden, Boat available, Washing machine, Car not required

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Price per night from

$190

Alice's Beach Bungalows 2 bedroom

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“A perfect spot for us and for our golden retriever!” What a great place to enjoy the beauty of Treasure Island. The bungalow that we stayed in was wonderful...clean, a well stocked kitchen, beach towels, a great backyard. Susan, the owner, was also great to work with on every level. She was attentive, often checking in on us to make sure all was going great with our stay. She was also responsive to our rental needs and responded immediately if we had a question, etc.. She also embraced our golden retriever and he, too, immediately became fast friends with Susan. This bungalow is literally a block from the beach, a short walk over the bridge to John's Pass and close to grocery shopping, lots of great restaurants right on the beach, etc.. A great experience and we will definitely plan to stay at this bungalow again!

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

3 of 5 filters match

Price per night from

$316

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

3 of 5 filters match

Price per night from

$1,148

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

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

3 of 5 filters match

Price per night from

$150

Historic Pass-A-Grille, Literally Seconds to Beach

St. Pete Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

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

3 of 5 filters match

Price per night from

$299

Beach Front Condo In Indian Rocks Beach

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 41 minutes

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

3 of 5 filters match

Price per night from

$211

ULTIMATE ST PETE BEACH FRONT RENTAL CONDO #101

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 5 match: Boat available, Garden, Washing machine, Horse riding, Car not required

2 of 5 filters match

Price per night from

$402

* Busch Gardens " Welcoming & Comfortable"

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Sunshine State Vacation Well Done!” We had an amazing time in this lovely Florida rental. I would highly recommend this place for families with kids. The house is clean and conveniently located near many fun things to do. Disney is only hour and fifteen minutes away which made easy for one day visit to Magic Kingdom! Host was friendly and resourceful. He was quick to respond to all of our questions and he offered advice on many great things to do in the area!

Responds fast! avg. 2 hours 59 minutes

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

3 of 5 filters match

Price per night from

$179

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

3 of 5 filters match

Price per night from

$158

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, Garden, Horse riding, Washing machine, Car not required

3 of 5 filters match

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, Garden, Horse riding, Washing machine, Car not required

3 of 5 filters match

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, Garden, Horse riding, Washing machine, Car not required

3 of 5 filters match

Price per night from

$150

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

2 of 5 match: Horse riding, Garden, Boat available, Washing machine, Car not required

2 of 5 filters match

Price per night from

$345

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

2 of 5 match: Horse riding, Garden, Boat available, Washing machine, Car not required

2 of 5 filters match

Price per night from

$148

BAY VIEW. SUNSETS. CLOSE TO ANNA MARIA ISLAND AND IMG ACADEMY

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

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

3 of 5 filters match

Price per night from

$368

Viewing 38 of 4,533
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