Holiday Homes in Florida Keys

Start date: Check-in selected.
To Date
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

Featured Holiday Homes in Florida Keys and around

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (61)
"Excelent place "
The price is €315
includes taxes & fees
28 Oct - 29 Oct
Waterfront Tiny House w Pool, Beach, and Boat Dock

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

9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is €387
includes taxes & fees
9 Oct - 10 Oct
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"Great location. Very clean very nice, stay there again"
The price is €293
includes taxes & fees
7 Oct - 8 Oct
Charming Home in Key Largo

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"Close to Key West. Would stay there again!!"
The price is €573
includes taxes & fees
14 Oct - 15 Oct
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

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

9.6 out of 10, Exceptional, (98)
"The house was very clean. Friendly and quiet location. The hosts were extremely helpful. "
The price is €366
includes taxes & fees
19 Oct - 20 Oct
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (119)
"We enjoyed our stay! Great little house and location. "
The price is €473
includes taxes & fees
26 Oct - 27 Oct
Kelly's Kabin - Adorable Private Summerland Key Cottage

Poolside Cottage #411

9.8 out of 10, Exceptional, (53)
"Nice area, quiet and clean"
The price is €257
includes taxes & fees
7 Oct - 8 Oct
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 €305
includes taxes & fees
7 Oct - 8 Oct
Kingfish Keep | Lively Escape on Duval! Balcony!

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

9.6 out of 10, Exceptional, (77)
"It was a nice place to stay! The home was super clean and cute!"
The price is €329
includes taxes & fees
2 Nov - 3 Nov
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

9.0 out of 10, Wonderful, (172)
"This place was perfect for me and my boyfriend! It was in a great area very convenient and parking was pretty easy to find nearby, the new updates were super nice and everything was really clean! Host was really nice and understanding, would definitely stay here again!"
The price is €287
includes taxes & fees
27 Oct - 28 Oct
Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (9)
"Greta property, really enjoyed the water view and the bbq grill "
The price is €595
includes taxes & fees
7 Oct - 8 Oct
Island Time #110 Ocean Views - Cudjoe Key

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

9.6 out of 10, Exceptional, (45)
"We had a good stay. Nice place"
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA

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

9.8 out of 10, Exceptional, (237)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
The price is €714
includes taxes & fees
7 Oct - 8 Oct
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

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 €266
includes taxes & fees
12 Oct - 13 Oct
Poolside Cottage #412

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (117)
"Deer in the front yard, perfect location, clean and friendly "
The price is €471
includes taxes & fees
12 Oct - 13 Oct
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Kawama L4 - Upscale Oceanside Villa with Marina

9.6 out of 10, Exceptional, (141)
"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!"
Kawama L4 - Upscale Oceanside Villa with Marina

🌴 TROPICAL RETREAT 🌴 RV in the Keys

10.0 out of 10, Exceptional, (2)
"Its clean and plenty of room.Outdoor seating is wonderful. Could use a gas grill. But definitely a great place."
The price is €238
includes taxes & fees
7 Oct - 8 Oct
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

9.8 out of 10, Exceptional, (113)
"Great location. Clean and beautifully decorated. "
The price is €469
includes taxes & fees
10 Oct - 11 Oct
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury two floor apartment in prime location of famous Duval Street

9.6 out of 10, Exceptional, (83)
"We truly enjoyed our stay there, and our interaction with the property owner was very pleasant. "
The price is €509
includes taxes & fees
7 Oct - 8 Oct
Luxury two floor apartment in prime location of famous Duval Street

Gone Coastal

9.8 out of 10, Exceptional, (17)
"Great place , clean and close to everything!"
Gone Coastal
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

Find out more about Florida Keys

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
Accommodation
Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia