Guesthouses Naples

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489 guest houses

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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Fort Myers / Sanibel Florida - Paradise on Palm

Iona house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$172

Lido Beach Villa, 1.2k sf, 1 block to the beach

Lido Key villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$184

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$230

*Just Launched* Fully-Stocked Clean Cabin in Tampa

Tampa house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$207

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$492

Lemon Cottage, Pets OK , 200 Steps to Beach

Clearwater cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$297

Pine Island Hideaway ~ competitive rates!

Bokeelia condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$131

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$516

Sunset Suite

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 1

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$172

Great 2/2 Sanibel Condo, Nice Pool, Private Beach

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Sunshine, beaches, What's not to love?” My husband and I stayed at this pleasant 2 bedroom condo with 2 grown children and one son-in-law. The two bedrooms and two baths worked fine for our group. Our married daughter and hubby had to share a bedroom with her brother. The furnishings in the condo were comfortable and clean without being too new to cause worry about a little sand. There were all sorts of beach toys and towels available. The kitchen had a full range of dishes and I cooked fresh fish from the local grocery store several nights. It was convenient to walk to the lovely uncrowded beach with no high-rises in sight. we kayaked with the condo's kayaks in the lagoon and saw a large range of birds, including an osprey feeding on a fish. We had gorgeous weather and collected quite a few shells. Would definitely return.

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$158

Spectacular Beachfront Condo-Private Beach/No Fees

St. Pete Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$356

“Wonderful Family Vacation with No Worries” Thank you! Our stay was lovely. The owners returned our phone calls, and were very willing to help if there was a need. The home was larger than the pictures depicted. We would love to return.

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$574

Luxury Waterfront Home

Marco Island house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 10

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$2,867

B-2 Breakers West, 2BR/2BA Condo, Olde-Fla Charm

Sanibel Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Clean, close to the beach, convenient, and perfect for our family vacation!” The condo is a few short steps away from the beach. The beach is beautiful, has a plethora of unusual shells, and is very clean. Susan and Andrew were quick to respond to communication. Thank you for making a memorable visit to the island.

Responds fast! avg. 2 hours 16 minutes

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$286

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$272

SURF AND TURF ACTIVITY FILLED GOLF RESORT COMMUNITY

Venice villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 31 minutes

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$86

Cheerful Vacation Home!

Northdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 23 minutes

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$253

Trendy 4bd3bath Home in St Pete Arts District

St. Petersburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$207

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

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$266

Villa Alamea - Yacht Club area - Luxury vacation home - boaters dream

Cape Coral villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A wonderful place to spend a vacation!” We had a great time at Villa Alamea! The home is beautiful and has every amenity imaginable. We vacationed with 3 generations of family and enjoyed the pool and outdoor living space as well as the indoors. I would definitely recommend this home! The location was awesome as well.

2 of 3 match: Rental types, Cycling trips, Housekeeping Included

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Price per night from

$860

North - Sunset Hide Away in Paradise

Naples guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 22 minutes

2 of 3 match: Housekeeping Included, Rental types, Cycling trips

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Price per night from

$297

West - Sunset Hide Away in Paradise

Naples guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 22 minutes

2 of 3 match: Housekeeping Included, Rental types, Cycling trips

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Price per night from

$255

LUX Townhome 15m to Beach & 5th Ave! EV Charger!

Naples townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$390

Close to Siesta key with hot tub, fire pit and butterfly garden

Gulf Gate Estates guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Housekeeping Included, Rental types, Cycling trips

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Price per night from

$193

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$155

Villa with pool & boatdock

Cape Coral villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 54 minutes

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$155

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

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$148

3 bed luxury Waterfront resort Marco Island

Marco Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$524

Marco Island Paradise, on the water AMAZING VIEW!

Marco Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$258

Affordable Luxury 2+2 Condo Lots of Amenities

Naples house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$100

BEACH FRONT CONDO *** MADEIRA BEACH

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$368

“Beautiful relaxing home” Villa, Sunny Breeze is a large beautiful home on canal. Just bring our suitcase. All other items to run a home were furnished. Easy to locate and convenient to local grocery, gas stations and shopping. All questions were promptly answered. Would highly recommend.

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$115

Beautiful 3 bedroom home in Southwest Florida

Port Charlotte house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Relaxing Stay” Well kept property in a great neighborhood within 15 min from the beach and great shopping. The pictures and description accurately reflect what you see when you get there. Owners, Lorrie and Frank, were a pleasure to deal with from beginning to end. Had a wonderful time and looking forward to returning soon. Would highly recommend this property!

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$172

South -Sunset Hide Away in Paradise

Naples house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Responds fast! avg. 22 minutes

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

1 of 3 filters match

Price per night from

$297

Sanibel island 3bdrm home Walk2Beach

Sanibel Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$287

Steps to the pool!! Professionally renovated and decorated!

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$104

1 of 3 match: Rental types, Housekeeping Included, Cycling trips

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Price per night from

$183

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rentals in Naples

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