Search Vacation Homes in Florida Keys

Start date: Check-in selected.
End date: Check-out
    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

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Florida Keys

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (59)
"My wife and I stayed here for our honeymoon , and we were absolutely thrilled with everything. We loved that the house had a bunch of mini splits to keep it nice and chilly. We also loved that the house was very clean and well kept. The tiki hut on the water with the tv and great lighting at night makes a perfect place to relax at the end of a fun filled day. All around this was a fantastic place to stay!"
The price is AED 393
AED 1,249 total
includes taxes & fees
3 Sep - 4 Sep
Waterfront Tiny House w Pool, Beach, and Boat Dock

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AED 896
AED 2,184 total
includes taxes & fees
3 Sep - 4 Sep
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

9.8 out of 10, Exceptional, (81)
"The house was clean as a whistle, has tons of storage, came with everything you need, and is well located. Our husbands really loved the boat launch and docking, the pool and amenities are well kept, security in the park was well done, and the owner are very pleasant and responsive."
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.6 out of 10, Exceptional, (74)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is AED 329
AED 1,218 total
includes taxes & fees
3 Sep - 4 Sep
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (119)
"We enjoyed our stay in Kelly's Kabin. The house was very clean and comfortable, and was in a great location for exploring the mid to lower Keys. "
Kelly's Kabin - Adorable Private Summerland Key Cottage

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is AED 698
AED 1,716 total
includes taxes & fees
3 Oct - 4 Oct
Charming Home in Key Largo

Poolside Cottage #411

9.8 out of 10, Exceptional, (52)
"Lovely home to stay in for a couple of nights on Key West"
Poolside Cottage #411

Kingfish Keep | Lively Escape on Duval! Balcony!

10.0 out of 10, Exceptional, (18)
"Awesome location with excellent communication. "
The price is AED 367
AED 1,187 total
includes taxes & fees
8 Sep - 9 Sep
Kingfish Keep | Lively Escape on Duval! Balcony!

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
The price is AED 547
AED 1,601 total
includes taxes & fees
3 Sep - 4 Sep
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (136)
"This property was perfect in the heart of key largo with pool and ocean access. Had everything we need and even included two bikes! Great stay overall!"
The price is AED 984
AED 2,126 total
includes taxes & fees
21 Sep - 22 Sep
Kawama L4 - Upscale Oceanside Villa with Marina

Charming 3-bedroom house in Big Pine Key near Beach and Key West

The price is AED 658
AED 2,042 total
includes taxes & fees
3 Sep - 4 Sep
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Poolside Cottage #412

9.2 out of 10, Wonderful, (25)
"The property and our place was really nice. Would definitely stay again. "
The price is AED 612
AED 1,075 total
includes taxes & fees
3 Sep - 4 Sep
Poolside Cottage #412

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (7)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is AED 973
AED 2,282 total
includes taxes & fees
3 Sep - 4 Sep
Island Time #110 Ocean Views - Cudjoe Key

Villa 5053 on Duck Key BOAT SLIP available

9.6 out of 10, Exceptional, (45)
"We had a good stay. Nice place"
Villa 5053 on Duck Key BOAT SLIP available

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

9.6 out of 10, Exceptional, (134)
"Very nice villa"
The price is AED 1,047
AED 2,213 total
includes taxes & fees
3 Sep - 4 Sep
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (237)
"Clean and inviting property, great location, attentive host. Highly recommend."
The price is AED 1,286
AED 3,003 total
includes taxes & fees
3 Sep - 4 Sep
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

2.0 star property
9.0 out of 10, Wonderful, (7)
"Loved the location! Very nice park. Our place had an amazing view to watch the sunrise and to enjoy a nice home cooked meal before heading up to the pool."
The price is AED 973
AED 2,282 total
includes taxes & fees
3 Sep - 4 Sep
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Casa Largo

9.0 out of 10, Wonderful, (127)
"Victor’s place was as advertised. Great location, walk to water front restaurants and music. Lots for a family to do on the grounds.Thanks, Victor!"
The price is AED 918
AED 2,024 total
includes taxes & fees
3 Sep - 4 Sep
Casa Largo

Beautiful Kawama Townhouse

9.8 out of 10, Exceptional, (137)
"Great location, well stocked kitchen, bathrooms, etc. Excellent host, had a great time in a beautiful community. The lagoon is a great feature."
The price is AED 918
AED 2,087 total
includes taxes & fees
4 Sep - 5 Sep
Beautiful Kawama Townhouse

Beach House Getaway - Kayaks & 2-2.5 Villa

9.8 out of 10, Exceptional, (28)
"Great location for day trips and very clean, well stocked apartment. "
Beach House Getaway - Kayaks & 2-2.5 Villa
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