Holiday Homes in Florida Keys

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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Florida Keys holiday homes

Outdoor dining

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (46 reviews)
"I really enjoyed our stay at the campsite. The home is right on the water with plenty of activities to do. Also the grocery store and places to eat are only a few minutes away. "
United States
Everett S.
The price is €310
includes taxes & fees
29 Apr - 30 Apr
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (123 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
The price is €463
includes taxes & fees
3 May - 4 May
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is €480
includes taxes & fees
2 May - 3 May
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor dining

Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (31 reviews)
"Everything you need for a great stay!!"
United States
Karen D.
Poolside Cottage #412
Outdoor dining

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (62 reviews)
"This was a beautiful property, great location and awesome amenities. We loved it and will highly recommend it! "
United States
Kim H.
Poolside Cottage #411
Beach towels

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.4 out of 10, Exceptional, (92 reviews)
"Clean and cute tiny house. Simple and easy check in at campground, very nice staff there . "
United States
Tami B.
The price is €404
includes taxes & fees
4 May - 5 May
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Exterior

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (106 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is €423
includes taxes & fees
13 Apr - 14 Apr
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (16 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is €406
includes taxes & fees
23 Apr - 24 Apr
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
9.2 out of 10, Wonderful, (9 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €505
includes taxes & fees
13 Apr - 14 Apr
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Terrace/patio

Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (8 reviews)
"Location, friendly neighbors, calming courtyard."
United States
Jim C.
Road's End | Prime Old Town Location! Updated Home w/ Pool
Marina

4. Cozy Waterfront Apartment in Key Largo!

4. Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (12 reviews)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
4. Cozy Waterfront Apartment in Key Largo!
Beach

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

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"My family and I had a great time. The place was very comfortable. Location was great and we enjoyed all the amenities. Great experience over all."
United States
Raul e.
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Beach nearby

Beautiful Kawama Townhouse

Beautiful Kawama Townhouse
Key Largo
9.8 out of 10, Exceptional, (145 reviews)
"The host, house and amenities were perfect. all praises.."
United States
Pete S.
The price is €546
includes taxes & fees
3 May - 4 May
Beautiful Kawama Townhouse
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (36 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is €520
includes taxes & fees
13 Apr - 14 Apr
Paradise found
Property grounds

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Stock Island
9.8 out of 10, Exceptional, (20 reviews)
"We stayed for a week and the condo was perfect. Beautifully decorated & very clean. The balconies were an added plus. It’s a perfect location for access to the pool. Roostica is a great Italian restaurant in walking distance. And a delicious French bakery nearby too."
United States
Joan Z.
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
Terrace/patio

House of the Rising Sun - VO479

House of the Rising Sun - VO479
Cudjoe Key
8.8 out of 10, Excellent, (13 reviews)
"We rented a boat, fished and snorkeled. Really enjoyed the patio right on the sea wall. One of the best parts of property was the stunning view of the morning sunrise!"
United States
Matt W.
The price is €643
includes taxes & fees
23 Apr - 24 Apr
House of the Rising Sun - VO479
Property grounds

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (51 reviews)
"super nice and modern house, really lovely host, the kitchen is equipped with all you need for cookingall decoration is so nice fits to the beach feelingall rooms are modern and nice decoratedwe could just recommend ! if we will come back to Florida this will be again our choice!"
United States
Anonymous traveller
The price is €631
includes taxes & fees
16 Apr - 17 Apr
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Indoor pool, outdoor pool

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (96 reviews)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
The price is €687
includes taxes & fees
27 Apr - 28 Apr
Ohana Cay 2brm/2bth - Book your getaway!
Interior

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

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.0 out of 10, Very good, (9 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is €636
includes taxes & fees
22 Apr - 23 Apr
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Property grounds

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

Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
Duck Key
9.6 out of 10, Exceptional, (51 reviews)
"Clean property! Great views! Great communication with owner! Perfect location- close to marathon and key west! "
United States
candi b.
The price is €569
includes taxes & fees
13 Apr - 14 Apr
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
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.
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Top Florida Keys Hotel Reviews

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

8/10 Good
"The room is pretty clean, and the beach is absolutely amazing."
Hong 1-night trip
Posted 3 hours ago
The Pelican Key Largo Cottages

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
1,005
Accommodation
972 Holiday Homes
Lowest Price
€310
Highest Price
€687