Florida Keys Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Florida Keys

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (195)
"We loved our weekend stay here. "
Yacht Haven Marina

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (513)
"Best kept secret, love staying here,!"
The price is AU$215
includes taxes & fees
15 Sept - 16 Sept
Breezy Palms Resort

Cabins at Bonefish Bay

3.0 star property
9.8 out of 10, Exceptional, (59)
"Awesome cabins!"
Cabins at Bonefish Bay

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (256)
"River boat houses, pool, kayak rentals. "
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.6 out of 10, Excellent, (849)
"Super cute little cottage with a great location, would definitely stay again!"
The price is AU$147
includes taxes & fees
21 Aug - 22 Aug
Tropical Cottages

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (100)
"Unique House boat experience, friendly staff. "
The price is AU$372
includes taxes & fees
2 Sept - 3 Sept
Treasure Harbor

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1198)
"Great stay"
Skipjack Resort & Marina

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (66)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,038
includes taxes & fees
21 Aug - 22 Aug
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.6 out of 10, Exceptional, (24)
"Beautiful and peaceful place "
Key Largo Cottages

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1141)
"Nice roomy accommodations and helpful staff I would stay here again "
The price is AU$154
includes taxes & fees
7 Sept - 8 Sept
Knight's Key Suites

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"Very nice and clean nice pool area nice tity bar an restant easy to get in and out good gym area"
The Hammocks at Marathon

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (49)
"Great place to stay. A small area but otherwise a nice place. I would suggest a plunger for the "
Aqua Lodges at 47th Street Gulfside

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (130)
"Clean, friendly, has its own beach"
Island Bay Resort

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (178)
"Very very nice place"
Aqua Lodge Rentals At Coconut Cay

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"Took the team down to the keys for a little R&R"
Old Florida Style, wrap around porch, boat basin for dockage, open water

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (293)
"All around amazing place"
The price is AU$327
includes taxes & fees
21 Aug - 22 Aug
Anchorage Resort & Yacht Club

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.4 out of 10, Exceptional, (72)
"Property was great for our group. 2 miles to grocery stores. Pool was great! Used the bikes and had a great time here. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

Piece of Paradise located at Hawks Cay in Duck Key

9.4 out of 10, Exceptional, (3)
"Amazing place. "
Piece of Paradise located at Hawks Cay in Duck Key

Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

8.8 out of 10, Excellent, (29)
"So enjoyed our stay here with a couple friends. Place has everything you need, is immaculate, fantastic view, and so close to either the beach in one direction and grocery stores in the other. Also located in a very nice residential neighborhood. Plan on returning! Thanks for the lovely stay!! "
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (66)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Florida Keys Hotel Reviews