Florida Keys Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Florida Keys

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"The pictures online do not do this place justice. Tucked between two larger hotels, it’s like an oasis. Our room in particular had a grassy lawn facing the water, was spotless and well appointed. Small beach, pool and sandy area (volleyball court) is adjacent to a dock and boat launch for interesting views. Lots of iguanas and a local rooster completes the ambiance. "
The price is S$293
includes taxes & fees
13 Feb - 14 Feb
Breezy Palms Resort

Old Wooden Bridge Resort and Marina

2.5 star property
8.4 out of 10, Very good, (187)
"Great location and our houseboat was perfect. "
The price is S$333
includes taxes & fees
3 Feb - 4 Feb
Old Wooden Bridge Resort and Marina

Skipjack Resort & Marina

3.0 star property
8.6 out of 10, Excellent, (1149)
"Rooms are dated, could use a few more things in the very small kitchen, building is showing it’s age, decent place to stay."
The price is S$597
includes taxes & fees
3 Feb - 4 Feb
Skipjack Resort & Marina

Yacht Haven Marina

3.5 star property
9.8 out of 10, Exceptional, (108)
"Great people, comfortable. Had a deep and restful sleep. "
The price is S$672
includes taxes & fees
5 Feb - 6 Feb
Yacht Haven Marina

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (47)
"Beautiful property with great staff! "
The price is S$982
includes taxes & fees
2 Mar - 3 Mar
The Islands of Islamorada

Tropical Cottages

3.0 star property
8.4 out of 10, Very good, (775)
"From the moment we opened the door, we felt welcomed. The room was spacious and had touches of hospitality from the bedding to the bureau with a coffee area. The roosters woke us early! We saw a manatee from the the dock outside. "
The price is S$258
includes taxes & fees
3 Feb - 4 Feb
Tropical Cottages

Knight's Key Suites

3.0 star property
9.0 out of 10, Wonderful, (1081)
"I don’t like remote anything. There is no one at the property. If you have a problem, need something, need directions or just a recommendation for dining your out of luck."
The price is S$286
includes taxes & fees
4 Feb - 5 Feb
Knight's Key Suites

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (135)
"To be fair, its the first time we stay at a houseboat so we didn't know what to expect. We just needed a place to sleep because we planned our two days to be out and about doing activities. Overall the place fitted our needs: we had the 3 beds we needed to sleep all of us & the mattresses were comfortable to have a goodnight of sleep. It was clean, we had the extra blankets I requested due to the temperature was going to get colder for the weekend and it was dog friendly. What we didn't expect...
The price is S$470
includes taxes & fees
4 Feb - 5 Feb
Aqua Lodge Rentals At Coconut Cay

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is S$638
includes taxes & fees
9 Feb - 10 Feb
Key Largo Cottages

Aqua Lodges at 47th Street Gulfside

3.0 star property
8.6 out of 10, Excellent, (19)
"Had a wonderful time. So much to do in the area. We enjoyed the Cabana Club beach only a short drive away and included in the fee. We were there for the coldest week of the year. The maintenance gentleman, Scott and his assistant were kind enough to bring a hard to find space heater that kept us toasty warm as well a giving spot on recommendations for great places to eat. Some construction in the area but tolerable. Hope to return someday. "
The price is S$504
includes taxes & fees
10 Feb - 11 Feb
Aqua Lodges at 47th Street Gulfside

Island Bay Resort

2.5 star property
9.8 out of 10, Exceptional, (98)
"This boutique cottage-based resort is a gem. We found the owners/operators (Steve & Sue) to be gracious and super-friendly as they seek to accommodate their guests and keep everything looking picture-perfect. It's a bit of paradise!"
Island Bay Resort

Anchorage Resort & Yacht Club

3.0 star property
8.6 out of 10, Excellent, (274)
"We loved our stay and the central / gated location was perfect! The view from all of the rooms balconies face the water to enjoy the sunset and it’s small enough to feel very private. Loved the bar restaurant, The Black Siren, next door! The service, food and drinks were perfect! Yes, it a bit dated but we knew that and it added to the fishing village vibe. We would definitely stay again! "
The price is S$343
includes taxes & fees
9 Feb - 10 Feb
Anchorage Resort & Yacht Club

Cabins at Bonefish Bay

3.0 star property
10.0 out of 10, Exceptional, (29)
"I have to say that I loved this place, one of my favorite. Very peaceful , family oriented, good for all type of ages. Looking forward to go again. Thank you Sabrina "
Cabins at Bonefish Bay

Indigo Reef Resort Villas & Marina by KeysCaribbean

3.5 star property
9.2 out of 10, Wonderful, (49)
"The unit we stayed in was very clean, beds comfy. The unit itself is showing some wear and tear but that did NOT affect the cleanliness. The view of the ocean was why i chose to stay here and was not disappointed. The patios of each unit are fairly close and do not lend alot of privacy--not genetally a problem, unless the neighbors decide to get affectionate (if you know what I mean 😀) The pool was clean and offered plenty of seating. I would definitely stay here again."
Indigo Reef Resort Villas & Marina by KeysCaribbean
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.
Don't see what you're looking for?
See all available properties in Florida Keys
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Florida Keys you may be interested in

Marina Del Mar Resort and Marina

2.5 star property
8.4 out of 10, Very good, (1366)
"Fun location on the canal with lots of boat traffic to watch "
The price is S$251
includes taxes & fees
3 Feb - 4 Feb
Marina Del Mar Resort and Marina

Baker's Cay Resort Key Largo, Curio Collection by Hilton

4.0 star property
8.6 out of 10, Excellent, (1012)
"I felt right at home here. Felt like I was away in the Caribbean. All staff members met you with a warm friendly greeting. The food was amazing!!!!! I would say my only complaint is that I wish I had made my stay a little longer. I absolutely loved every moment of my stay here!"
The price is S$721
includes taxes & fees
9 Feb - 10 Feb
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Isla Bella Beach Resort & Spa

5.0 star property
9.0 out of 10, Wonderful, (1008)
"Everyone is very friendly and helpful. Food in the restaurant is amazing room service is fantastic very quick delivery. This is our second time in this resort and I highly recommend it"
The price is S$673
includes taxes & fees
3 Feb - 4 Feb
Isla Bella Beach Resort & Spa
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.