Vacation Rentals & Apartments in Naples

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4,155 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. 45 minutes

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$138

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!

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$316

Sea Club II - 1B: By Beachside Management

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$240

Lookout: By Beachside Management

Siesta Key house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$743

Quiet S.Tampa

Tampa townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 42 minutes

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$150

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

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$114

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

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$117

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$2,289

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$1,259

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$1,145

Tropical Escape Sarasota - Discover Real Florida Up-Close!

Lockwood Ridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$149

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Bicycles available Washing machine Horse riding Car not required

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Price per night from

$975

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Modern Beach Getaway Downtown FMB

Fort Myers Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$201

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$490

Luxury waterfront retreat with Sailing

Saint James City b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$860

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$315

Close to everything. w/2 Bikes

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 9 minutes

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$79

Costal Surfside Swank 302: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$514

Direct Beachfront Delight: By Beachside Management

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$240

Palm Bay Club - 343: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$285

Beach House Residence - Penthouse; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$434

Costal Surfside 298: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$457

Costal Surfside 304: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$297

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: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$573

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Location, Very Well Appointed” This house is perfectly located right in Siesta Key Village within an easy walk to shops and restaurants. It is also just a block from the beach. No parking hassles! The house is very well appointed. The owner has thoughtfully provided more than enough coffee for the Keurig, lots of towels, and all needed kitchen utensils, dishes, containers, and cooking supplies, in addition to a beach wagon and chairs. Although not luxurious, this is a very comfortable rental. We also liked the privacy of having our own house. The only negatives were the lack of towel racks in the bathrooms and the lack of hot water in the bathroom with the tub (it remained only warm, even after running for a very long time). The water in the other bathroom was fine.

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$316

Ocean Vue - Unit A: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$514

Bianco Sands - 1 Bedroom 1 Bath: By Beachside Management

Siesta Key villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$251

Ocean Vue - Unit B: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$526

Sol y Mar - Casita Mar: By Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$240

Fanta-Sea 47; By Beachside Management

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$457

Crescent Beach Villas - La Perlita: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$274

Sea Club II - 11E: By Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$228

Bianco Sands - 2 Bedroom - Poolside: By Beachside Management

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$331

***WINTER AND SPRING SEASON FILLING FAST!!! BOOK YOUR ESCAPE FROM THE COLD!!***

North Captiva Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$744

Just Beachy: By Beachside Management

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$377

Beach Walk: By Beachside Management

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

3 of 4 filters match

Price per night from

$514

Ten35 Seaside - Direct Gulf View: Residence 501

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

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Price per night from

$949

Bianco Sands 2 Bedroom - 2 Bath; by Beachside Management

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Horse riding, Bicycles available, Washing machine, Car not required

3 of 4 filters match

Price per night from

$297

Viewing 38 of 4,155
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