Vacation Rentals & House Rentals in Florida Keys

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129 house rentals

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. 2 hours 26 minutes

Match: Swing set or jungle gym Private pool

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Price per night from

$602

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Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$361

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$393

Florida Keys Splendor at Hammer Point

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Winter Paradise!” My wife and I stayed at this great place in January 2014 and it was wonderful. It was very clean and well maintained. The canal was great to watch the fish jump and we saw Manatees almost every day. We especially liked the kayak and did a lot of site seeing from the ocean side. Migdy was great to work with and very accommodating. We would highly recommend this place to anyone.

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$157

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$264

Penthouse Sunsets and Tropical Breeze in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great place for a family of 5” Loved the condo, it was family friendly and very spacious. We had a great view from our deck. The owner was very friendly and very helpful. The facility had a great tennis court and we loved the lagoon. This unit was a great value and the owner makes it affordable for the average family to be able to spend time there.

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$315

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$457

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$289

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$918

Key Colony Beach Oasis

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$1,154

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$437

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$412

Immaculate Waterfront ~ 2 BR ~ Private Pool, Tiki on Canal! 2 Min Walk to Beach!

Key Colony Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$344

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$556

Relax Away- SOMBRERO BEACH- NEW 4BDRM W/ 40FT DOCK & POOL

Grassy Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$567

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$773

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$573

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$307

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$481

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

Islamorada apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$201

FALL IN LOVE with your home away from home!

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$206

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$476

Ocean Breeze Oasis With Excellent Boating Access

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$602

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$285

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$320

Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$784

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 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

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$327

BREATHTAKING Ocean views await at Tropical Daze

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Couldn't be better!!!” If you are looking to rest and relax, look no further.

Responds fast! avg. 2 hours 17 minutes

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

“Fantasic wedding on paradise!!” We picked Shadow Point because of it's fabulous secluded view and beautiful gardens on 2.5 acres. The house and cottage held up to 16 of us and was wonderfully decorated with period antiques. Our guests loved playing at their beach and kayaking and swimming around Key LargoSound. Our wedding was perfect with the full moon rising over our reception. We danced the night away in paradise.

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$2,405

Luxury Vacation Rental Oceanfront in Key Largo, nr, Islamorada, Florida Keys

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Great place to stay” We stayed at Sally and andrew´s place for a week. When we looked for a place to stay, we wanted a place not to far of Key West and Miami, and this place was just great! There were lots of places to eat out, things to see, and Key West and Miami was not to far away. The apartment was great, Andrew was too! Everthing regarding the stay were done in a professionel way. Both before the stay and after. The way of paying could have been easier though, but that is not a big problem We had a great time, all four of us visiting from Norway. If anyone should ask me where to stay in that erea, I have absolutely no problem telling them about Sally and andrew´s place! Ps: Make shure to have the time to eat at Mrs Mac´s Kitchen...

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$206

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$258

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private pool, Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$981

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$2,209

Beautiful Beachfront Home w/Heated Pool+45' Dock

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$801

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$1,317

"Irish Ayes" Elegant Waterfront Home with Pool

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private pool

1 of 2 filters match

Price per night from

$802

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