Vacation Rentals & House Rentals in Key West

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45 house rentals

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Swing set or jungle gym

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Price per night from

$264

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Swing set or jungle gym

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Price per night from

$158

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Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$205

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$377

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$524

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$819

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$343

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,140

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$613

New Listing! Charming Angler's Reef Home with Pool, Dockage

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$458

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$206

New Listing! Gone Coastal-Waterfront Bring Your Boat! Cabana Club Membership

Key Colony Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$217

Efficiency 8a, located 50 yards from Ocean

Grassy Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

8c, Efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

Unit 8b, small efficiency located 50 yards from Ocean

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$206

Newly refinished condo open water views very nice

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$229

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$654

Reef Resort - Peaceful Getaway 204

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“A lovely condo” The condo was nicely appointed and was a great mid location to explore the Florida Keys. The pool was large & refreshing. There were bikes, kayaks & paddle boats to use. We met a few residents who were very friendly. A very nice condo!

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$352

Reef Resort Getaway 205

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

Bayside Condo, marina, pool and beach

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Phenomenal keys experience!” This bay front condo is the perfect destination for the entire family! The fishing ranks up with the best in the world, there are plenty of other activities, and Key West is just a short trip down the beautiful HWY 1. I've had the pleasure of staying at this condo several times and have honestly never had a bad time (even during a cat 5 Trop Storm). There is too much to do, the condo is comfy, and the weather is always beautiful. Definitely recommend this condo!

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$253

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$321

Unit 9, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$252

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$81

Outstanding Oceanfront Condo on the Beach!!

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$343

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$487

Amazing Ocean View Condo on the Beach!

Marathon apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our Spirits were renewed!” Things don't happen by chance! Little did we know six months ago when we booked our vacation how much we would really, really NEED a quiet and peaceful week! This little corner of Marathon is exactly that: quiet and peaceful. The condo is very comfortably furnished, very clean, and the view is - well, I don't think there is a 'better' view anywhere! It's picture perfect - even to the gorgeous green iguana on the palm tree! (but you have to look quick - they move fast!). We had our son, daughter in law and two little grandkids with us...it was perfect! Sunrise with coffee by the pool, under the Chickee or on the patio...awesome! Lots to do for families or singles very close by...yup...you really can even have pizza delivered if you don't want delicious, fresh seafood!..and wow! are there some awesome spots for that!! Communication with the owners is impeccable...could NOT be better. These are the folks with whom you love to do business!! Thanks so much, Todd and Jamie!

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$343

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: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$487

Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend

Responds fast! avg. 1 hour 59 minutes

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$320

LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$355

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,946

2-Story condo w/ panoramic views and balconies

Marathon condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$373

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: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$307

Paradise at Islamorada

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$161

500 Ocean - Tropical Florida Keys Vacation Home

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Zen Oasis with a Dock” Loved 500 Ocean. Quiet, Local, Relaxed. Great location, Good fishing and amenities for the boat ( tons of dock space, bait freezer, fish cleaning station) You have to watch that canal though it's super shallow (as in barely 2 feet most of the way). Everything is the house was nice and comfortable. Coconut Chuck was super helpful with our stay and provided a lot of information ahead of time!

Responds fast! avg. 2 hours 56 minutes

1 of 2 match: Shared outdoor pool (heated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$327

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (heated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 48 minutes

1 of 2 match: Shared outdoor pool (heated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$544

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