Vacation Rentals & Apartments in Naples

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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 1 minutes

Match: Boat available Internet access Staffed property City breaks

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Price per night from

$267

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Boat available Internet access Staffed property City breaks

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Price per night from

$172

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The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$345

Glamorous 3-Bedroom Villa w Pool Sarasota Area

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 59 minutes

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$573

Amazing Condo at the Naples Bay Resort Cottages

Naples apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

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Price per night from

$320

#1 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$345

#2 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$345

#5 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$345

#10 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$459

#8 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$345

#4 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$345

#9 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$345

#3 Boutique Beach Retreat, Heated Pool, Private Room Outside Access/Corridor

Treasure Island hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$345

Old Southern Charm - Spacious & Centrally Located

Tampa apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Traveling grandmother, with grandchildren, enjoyed stay” When I choose a place to stay, I have five basic requirements. I want to feel secure and safe. The location has to be convenient to the airport and local attractions, or places we plan to visit. It also has to be clean, comfortable and affordable. This Songbird Property had all this and many extras, including a new toothbrush for my grandson after he conveniently forgot to pack his. My grandchildren and I enjoyed our stay in Tampa!

Responds fast! avg. 1 hour 56 minutes

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$212

Apartment Pelican in Fort Myers

Fort Myers apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

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Price per night from

$169

Apartment Manatee in Cape Coral

Cape Coral apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

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Price per night from

$303

Apartment Butterfly in Fort Myers

Fort Myers apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

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Price per night from

$298

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$258

Boutique Beach Events Hotel Takeover! 11 Private Rms, Sleeps 50 w/Event Space

Treasure Island hotel apartment

  • 12 bedrooms
  • 11 bathrooms
  • sleeps 49

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

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Price per night from

$3,098

Villa American Eagle/Cape Coral

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$224

Once upon a tide Guest Suite

Tampa villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 25 minutes

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$126

Sea Gem 803

Naples apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$201

Downtown Starfish 807

Naples apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$201

Beach Luxury 805

Naples apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$201

Casa Alma a Beautiful Historic Home in Ybor City

Tampa house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$253

Five star Downtown Sarasota tropical garden Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Paradise Found in Downtown Sarasota” Absolutely charming, fully redone/ upgraded bungalow close to everything Sarasota has to offer. This was the third year running my wife & I have stayed at the wonderful home located minutes from Sarasota's best beaches, restaurants & shopping. We fully intend to return again next year! The two bedroom home is in pristine condition. Beautifully decorated, lovely hardwood flooring throughout with a fully stocked (appliances, crockery, pots/pans, cutlery, etc...) kitchen & renovated bathroom. Everything you need is provided, just arrive & settle-in. A huge projection screen in the living room, should you want to have an at-home movie night (rental Dvd's a 5-minute walk away @ Publix). There's also a regular flat-screen TV in the living room, as well as a wall-mounted TV in the bedroom. The backyard is, personally, my favourite part of the home. A screen-in lanai to eat in & a beautifully manicured backyard to relax in under the tiki hut or under the palm trees. There are a few seating areas throughout the backyard. Find the space you like the best, sit-back & relax with a cool cocktail- very civilized & very beautiful. You'll feel like you're in the Caribbean, not Florida in this backyard. Maureen & Pat, your hosts who, very conveniently, live right next door have provided everything you need, including all the beach chairs, umbrellas, beach towels, etc...to take along with you to Sarasota's beautiful beaches. Maureen has also provided tons of literature about the area in the house- restaurant menus, local mags, maps- everything. Maureen & Pat are always happy to suggest restaurants, beaches, shopping, golf, etc. They know Sarasota well, are friendly & happy to help in any way they can to ensure you have a wonderful stay. My wife & I can honestly say we love this property, have encountered no negatives about the place in three years of week-long stays & look-forward to our time there each year. We recommend this lovely home to everyone.

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

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Price per night from

$189

Luxury Modern Home in Historic Ybor | 6 Bedroom

Tampa apartment

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 3 minutes

2 of 4 match: Boat available, Staffed property, City breaks, Internet access

2 of 4 filters match

Price per night from

$572

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!

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

3 of 4 filters match

Price per night from

$487

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

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$482

Secure, Cozy & Cute Private Sleeping Studio for 2

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$234

Apartment Flamingo in Fort Myers

Fort Myers apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

3 of 4 filters match

Price per night from

$164

Studio Turtle in Fort Myers

Fort Myers studio

  • Studio
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

3 of 4 filters match

Price per night from

$134

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$144

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$144

Relax just steps from the beach!

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$171

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$475

Sea Winds Marco Island 301 Beautiful Beach Front Condo on the Gulf

Marco Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Boat available, City breaks, Internet access, Staffed property

3 of 4 filters match

Price per night from

$295

Kokomo Del Sol. Welcome to Paradise.

Tice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

3 of 4 match: Staffed property, City breaks, Boat available, Internet access

3 of 4 filters match

Price per night from

$447

Viewing 38 of 5,371
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