Vacation Rentals & House Rentals in Key West

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67 house rentals

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Central heating Swing set or jungle gym

All filters match

Price per night from

$158

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

Match: Central heating Swing set or jungle gym

All filters match

Price per night from

$326

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Central heating Swing set or jungle gym

All filters match

Price per night from

$284

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Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Central heating, Swing set or jungle gym

1 of 2 filters match

Price per night from

$263

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. 59 minutes

1 of 2 match: Central heating, Swing set or jungle gym

1 of 2 filters match

Price per night from

$542

Manatee Bay

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$260

Best waterfront view in Marathon, pool, golf, dock

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$152

PARADISE IN YOUR HANDS

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$217

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$113

Harbour Dream~3/2..DKKB24~McGinnis

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$671

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$799

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$770

The Butterfly Cottage

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$251

Islamorada cottage on deep water canal

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$286

ISLAMORADA WATERFRONT PARADISE with FREE DOCKAGE

Matecumbe Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

“Relaxing Weekend Getaway” We love this home! It is on a private dead-end street, and everything is just perfect. Kept the boat right at the dock, fished right there at night, took some nice boat rides through the back country, and relaxed in paradise. Wifi is good and fast (I had to do some work while we were there), and we can't wait to go back.

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$172

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$619

Royal Palm House

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Beautiful Home in Marathon” We truly loved this place, the home was clean, spacious and very comfortable! My husband still claims to this day that was the best sleep he has had in years and that's a big compliment coming from him! We loved having water access (although we didn't have a boat) it really made for some beautiful sunsets and sunrises! We found a couple of amazing restaurants that we visited on several occasions, the first and our favorite was Tarpon Creek following as a very close second was The Sunset Grill and Raw Bar, also our favorite breakfast spot became Juice Paradise Cuban Cafe (the best coffee). I'm only just now getting around to reviewing this place because we are planning another trip to the Keys in December and I was checking this place out and i didn't see our review and ask my husband about it (I thought he posted it and he thought I posted it), so finally 2 yrs later I'm giving our review!!! Unfortunately I see it's booked for our time frame and we are very disappointed about that but I know whoever booked it WILL NOT be disappointed! Thanks so much for an amazing experience, Gina & Scott PS we actually stayed Sept 2014 but it would only let me go back to Oct 2014! :-)

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$214

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$498

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 58 minutes

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$319

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, Central heating

1 of 2 filters match

Price per night from

$354

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$485

Islamorada Waterfront Paradise 2

Islamorada house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$514

2 BEDROOM 2 1/2 BATH VILLA WITH PRIVATE PATIO AND PLUNGE POOL

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 13 minutes

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$337

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$456

PARADISE OCEAN FRONT HOME

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$1,026

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$770

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$1,483

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: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$514

Cozy Keys Cottage Islamorada FL.

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 10 minutes

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$407

Waterfront Anchor House with Boat Basin and Ramp!

Little Torch Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$754

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$571

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$514

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$327

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$741

“Perfect get-away cottage exceeded our expectations.” Just back from enjoying the cottage, Conched Out, at Caribbean Soul Charters on Conch Key. Awesome rustic cottage with tons of nautical character and a sailboat right out the back door. Great location near Marathon allowed us to easily day trip up to Key Largo and down to Key West. My family took the 23' Compact sailboat out 3 times during the week and the sailing was awesome. Our boat was in great shape and the motor operated flawlessly. One of the best family vacations we've ever enjoyed. We can't wait to come back. The owners, Barry and Tammy Jo, were very friendly and great sources of local information.

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$326

mojito breeze getaway, islamorada

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 11

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$513

Villa Bella 3/3 with Private Pool and Dock

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$411

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Central heating

1 of 2 filters match

Price per night from

$371

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