Vacation Rentals & Apartments in Naples

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4,229 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 Kettle 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: Kettle, Horse riding, Boat available, Washing machine, Car not required

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Price per night from

$138

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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

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Price per night from

$859

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

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

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Price per night from

$114

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: Horse riding, Boat available, Kettle, 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

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

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Price per night from

$573

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

Fort Myers Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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

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Price per night from

$230

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$201

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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

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Price per night from

$975

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

North Captiva Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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

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Price 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: Horse riding, Boat available, Kettle, Washing machine, Car not required

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Price per night from

$744

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.

4 of 5 match: Horse riding, Boat available, Kettle, 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

4 of 5 match: Boat available, Horse riding, Kettle, 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

4 of 5 match: Boat available, Horse riding, Kettle, 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

4 of 5 match: Boat available, Horse riding, Kettle, 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

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

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Price per night from

$2,290

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

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

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Price per night from

$117

INTRACOASTAL GETAWAY HOME

Indian Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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

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Price per night from

$293

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: Horse riding, Boat available, Kettle, Washing machine, Car not required

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Price per night from

$643

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

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

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Price per night from

$224

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: Horse riding, Boat available, Kettle, Washing machine, 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.❤

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

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Price per night from

$189

“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.

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

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Price per night from

$297

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: Horse riding, Boat available, Kettle, Washing machine, Car not required

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Price per night from

$487

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: Horse riding, Boat available, Kettle, Washing machine, Car not required

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Price 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: Horse riding, Boat available, Kettle, Washing machine, Car not required

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Price per night from

$228

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

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

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Price per night from

$324

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

Redington Shores house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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

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Price per night from

$255

The Ultimate Florida Vacation

Poinciana villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place” Very cozy, out in suburbs. Neighborhood clean and friendly. Pools and outdoor basketball courts and activities for the kids.

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

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Price per night from

$110

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!

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

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Price per night from

$316

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, Kettle, Washing machine, Car not required

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Price per night from

$149

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$1,260

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

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Price per night from

$1,145

Tropical Bliss: Lazy River, 5 Pools, Bar, 2 Restaurants, Cabanas!

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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

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Price per night from

$458

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

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Price per night from

$482

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

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Price per night from

$597

Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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

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Price per night from

$338

Beach Front Condo In Indian Rocks Beach

Indian Rocks Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 41 minutes

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

4 of 5 filters match

Price per night from

$211

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