Vacation Rentals & House Rentals in Florida Keys

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33 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. 59 minutes

Match: Private outdoor pool (unheated) Swing set or jungle gym

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Price per night from

$545

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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 outdoor pool (unheated)

1 of 2 filters match

Price per night from

$207

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$775

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$912

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 outdoor pool (unheated)

1 of 2 filters match

Price per night from

$603

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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$158

Key Colony Beach Home

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$264

Coastal Key Largo Townhome with Ocean Views, Pool & Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$390

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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$316

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$458

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$159

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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$327

“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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$2,410

Peaceful ocean view retreat in the Florida Keys

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$259

EXECUTIVE BAY ISLAMORADA BY SoFLA VACATIONS

Islamorada townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

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. 24 minutes

1 of 2 match: Private outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$286

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 outdoor pool (unheated), Swing set or jungle gym

1 of 2 filters match

Price per night from

$207

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,213

Lobster Lagoon

Stock Island house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$976

Family Friendly House In Paradise

Summerland Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$517

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

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$316

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$402

Harbor Walk Hideaways

Key West b&b

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,303

OCEANFRONT LUXURY "Mar Azul"

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$501

Key Largo Ocean Front Villa with Dock and Incredible views

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 23 minutes

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$459

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Key West House

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$689

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$701

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, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$517

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,851

4 Bd w/Pool, Bayside - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$1,851

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$2,008

1 of 2 match: Swing set or jungle gym, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$247

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