Vacation Rentals & House Rentals in Florida Keys

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60 house rentals

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

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Price per night from

$911

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

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Price per night from

$622

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

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Price per night from

$496

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

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Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Staffed property Golf course on site or within 15 min walk

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Price per night from

$445

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$484

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$471

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$654

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Staffed property Golf course on site or within 15 min walk

All filters match

Price per night from

$523

These homes match some but not all of your filters. Clear all filters

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$516

Single Family Home, 3 Bedroom, 2 Baths, and Pool. Great Value!

Key West house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$165

Harbor Hideaway 4 Bedrooms-3 Bathrooms Waterfront- Indoor Pool

Marathon Shores house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$745

2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

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Price per night from

$487

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$802

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$572

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$343

Key Colony Beach-2 Bed 2 Bath Canal Front Home with Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$308

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$819

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$413

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$264

Tee by the Sea - Luxury 2/2 1/2, WIFI, pool, parking, Bikes, 3 night min.

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

1 of 2 match: Staffed property, Golf course on site or within 15 min walk

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Price per night from

$344

Sleeping Room, Private Entrance and use of RV Park Bathrooms, Beach and Marina

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$144

Motel Room #2, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$212

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$976

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$315

Spacious 1 Bedroom, Full Kitchen, Central Air, Beach, Marina and Docks

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Tranquil and friendly” This was a place we found after months of searching and having another owner cancel out on us. We came in with a pre judgement of the place and BOY were we wrong. Everyone is super nice, everyone there(employees and guests) are very caring and friendly. The apartment was very comfy and well equipped, although anextra blanky or throw would have been nice to have for the sofa lounging. We are only 4 days into it but all is great!

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$281

Spacious 1 Bedroom Duplex, Full Kitchen, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$281

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$281

1 Bedroom, Full Kitchen, Mini Split Air, Beach and Marina Apt #1

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$281

Motel Room #1, Private Entrance, Beach and Marina

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$212

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$281

Luxury Condominium in Old Town | Monthly Rental at Steamplant Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$315

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$263

Coconut Mallory Resort and Marina

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$346

Responds fast! avg. 2 hours 25 minutes

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$367

Islamorada Waterfront Paradise Getaway!

Islamorada house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Wonderful Romantic Get-Away” We absolutely enjoyed our stay here and would recommend it to others. The owners were very friendly and pleasant, and the apartment was incredibly clean. The tiki hut over the private lagoon was amazing. We kept finding little things all over the apartment while we were there - drinks, books, games, etc. It was a totally wonderful time, and we want to go back!

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$573

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Staffed property

1 of 2 filters match

Price per night from

$915

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