Vacation Rentals & House Rentals in Florida Keys

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112 house rentals

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$911

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$622

Hyatt Sunset Harbor

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$496

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$525

Hyatt Sunset Harbor

Stock Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$445

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$525

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) Golf course on site or within 15 min walk

All filters match

Price per night from

$484

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (unheated) 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: Shared outdoor pool (unheated) 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$487

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$308

1 of 2 match: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), 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: Shared outdoor pool (unheated), Golf course on site or within 15 min walk

1 of 2 filters match

Price per night from

$344

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$213

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,664

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$363

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$286

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$252

Waterfront luxury Villa (43) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Key West get away to Marathon” My now husband, two daughters, and myself decided to take a week during Spring Break to get out of Key West. We actually went to Marathon that week to get married! I search and searched for place. Mr. Zito was very quick to respond, very helpful, and pleasant. He even allowed us to take a drive up one day to see the villas. His wide was nice enough to show us around. When we stayed there is was very clean and in perfect condition for our arrival. I big thank you to the housekeepers! The full kitchen and grills outside allowed us to be able to grocery shop and not have to eat out every meal. A benefit when you have children! The location was very kid friendly. The sunsets were amazing! Everything was honestly perfect! We would take a monthly trip if we were able to!

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

NEW LISTING! Waterfront Villa (35) w/ boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (30) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront Luxury Villa (13) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (29) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“WONDERFUL!!!!!!!” Everything at this unit was excellent! Clean upscale unit! We are going to rent next year and planning it already. Peaceful, beautiful & clean! We couldn't have asked for anything better! Unfortunately we had to depart 2 days early due to business emergency but we will be back next year!!

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (34) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (14) with sunset views and boat slip

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

Waterfront luxury Villa (54) with sunset views and boat slip

Marathon villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Beautiful condo in a beautiful setting” Sitting on the front porch watching the sunset was one of the highlights of the trip. And the pool was the best we've ever swam in.

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Golf course on site or within 15 min walk, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$300

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