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, (174)
"We loved our weekend stay here. "
Yacht Haven Marina

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1192)
"Great stay"
Skipjack Resort & Marina

Breezy Palms Resort

2.5 star property
8.8 out of 10, Excellent, (488)
"Laid back atmosphere with renovated rooms."
The price is AU$179
includes taxes & fees
15 July - 16 July
Breezy Palms Resort

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (245)
"Old Wooden Bridge was one of the coolest and most relaxing spots my family and I have ever stayed at! House Boat was clean and wonderful view of the beautiful waters in Big Pine Key! Also we were greeted by Key Deer every night which was an Amazing experience! "
Old Wooden Bridge Resort and Marina

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (825)
"Cute place, convenient location"
The price is AU$188
includes taxes & fees
13 July - 14 July
Tropical Cottages

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (61)
"Absolutely outstanding resort. Legitimate 5 star property. "
The price is AU$1,022
includes taxes & fees
22 July - 23 July
The Islands of Islamorada

Treasure Harbor

3.0 star property
9.0 out of 10, Wonderful, (85)
"Very clean and great atmosphere "
The price is AU$407
includes taxes & fees
5 Aug - 6 Aug
Treasure Harbor

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (49)
"I loved the little cabins it was a great trip for my son’s graduation. "
Cabins at Bonefish Bay

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (125)
"Clean, friendly, has its own beach"
Island Bay Resort

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (42)
"Great place to stay. A small area but otherwise a nice place. I would suggest a plunger for the "
The price is AU$434
includes taxes & fees
14 July - 15 July
Aqua Lodges at 47th Street Gulfside

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1125)
"Nice pool area with view of the 7 mile bridge "
The price is AU$176
includes taxes & fees
4 Aug - 5 Aug
Knight's Key Suites

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"The stay was great and the property manager Jenn was amazing. Would stay again"
Key Largo Cottages

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

9.6 out of 10, Exceptional, (76)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
Old Florida Style, wrap around porch, boat basin for dockage, open water

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"We loved the location of the property and we also loved the entertainment/singer provided by lounge."
The Hammocks at Marathon

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (172)
"I absolutely loved this place and can't wait to go back. The boat was beautiful inside and had everything we needed. "
Aqua Lodge Rentals At Coconut Cay

THE PERFECT PLACE -PRIVATE ELEVATOR,DOCK,HEAT POOL. MARATHON LIC PLR2017-00465

9.4 out of 10, Exceptional, (48)
"We stayed with Grandchildren and loved how the property was central to many attractions in the area. "
THE PERFECT PLACE -PRIVATE ELEVATOR,DOCK,HEAT POOL. MARATHON LIC PLR2017-00465

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

9.6 out of 10, Exceptional, (69)
"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

Sombrero Beach Tropical Getaway in the Heart of Marathon

2.0 star property
10.0 out of 10, Exceptional, (6)
"this place was great . the owner was super nice and handled a small problem fast. as for location it was also great. close to beach. and resturants. we traveled to key west one day and had a blast..."
The price is AU$593
includes taxes & fees
26 July - 27 July
Sombrero Beach Tropical Getaway in the Heart of Marathon

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

10.0 out of 10, Exceptional, (83)
"Everything just great except need better vaccum"
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!

9.6 out of 10, Exceptional, (286)
"We enjoyed the amenities at the Yacht Club very much. It was never too busy. Very quiet at night. Close to other entertainment and good restaurants. "
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!
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