A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Holiday Homes in Florida Keys

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Florida Keys holiday homes

Outdoor pool, pool umbrellas, pool loungers

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (140 reviews)
"This was the perfect place, right on the ocean and a full kitchen so you can cook your own meals. The room was very clean, I loved that they had a laundry basket and laundry detergent in the room for you, came in handy seeing as we stayed for 7 days. Amazing place to watch the sunset from a hammock and we got lucky enough to see some nurse sharks at the docks right outside of our hotel."
United States
Andrew Jackson
The price is NZ$458
includes taxes & fees
8 July - 9 July
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Beach

Feb 3-10 $245 off the rates close beach full kitchen & patio

Feb 3-10 $245 off the rates close beach full kitchen & patio
Old Town Key West
9.6 out of 10, Exceptional, (252 reviews)
"Loved our stay here!"
United States
Kristin E.
The price is NZ$558
includes taxes & fees
2 July - 3 July
Feb 3-10 $245 off the rates close beach full kitchen & patio
Smart TV

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"The condo is extremely clean and has everything you need for your stay. "
United States
hillary w.
The price is NZ$721
includes taxes & fees
7 July - 8 July
Charming Home in Key Largo
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
7.8 out of 10, Good, (20 reviews)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is NZ$824
includes taxes & fees
6 July - 7 July
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
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)
"Had fun villa was in good condition."
United States
Michelle S.
The price is NZ$1,264
includes taxes & fees
12 July - 13 July
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
On the beach

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, (49 reviews)
"We had a great time. Loved the kayaks!!"
United States
Laurie S.
The price is NZ$674
includes taxes & fees
7 July - 8 July
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, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is NZ$930
includes taxes & fees
12 July - 13 July
Kelly's Kabin - Adorable Private Summerland Key Cottage
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, (16 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is NZ$863
includes taxes & fees
24 July - 25 July
Road's End | Prime Old Town Location! Updated Home w/ Pool
Outdoor dining

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (67 reviews)
"We had a wonderful stay. The house was very clean, the area was quiet and peaceful, and the pool was incredibly relaxing. We enjoyed it so much that we have already booked another stay."
United States
Tiara B.
The price is NZ$570
includes taxes & fees
29 July - 30 July
Poolside Cottage #411
A heated pool

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is NZ$999
includes taxes & fees
8 July - 9 July
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Outdoor dining

Poolside Cottage #412

Poolside Cottage #412
Key West
9.2 out of 10, Wonderful, (32 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
Poolside Cottage #412
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is NZ$1,116
includes taxes & fees
6 July - 7 July
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
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, (53 reviews)
"Very nice villa "
United States
Grace L.
The price is NZ$1,137
includes taxes & fees
1 Aug - 2 Aug
Villa 5053 on Duck Key Boat Slip Available - 2BD 2.5BA
A heated pool

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is NZ$1,046
includes taxes & fees
6 July - 7 July
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Marina

Cozy Waterfront Apartment in Key Largo!

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.
Cozy Waterfront Apartment in Key Largo!
Exterior

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

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is NZ$961
includes taxes & fees
13 July - 14 July
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
House

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is NZ$1,263
includes taxes & fees
7 July - 8 July
Starlight Serenity - Hideaway w Stunning Views
Pool

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is NZ$1,295
includes taxes & fees
29 July - 30 July
Paradise found
Exterior

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is NZ$961
includes taxes & fees
13 July - 14 July
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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, (57 reviews)
"Great amenities. Immaculate apartment. Kids loved the lagoon. Super responsive host. Note - beds are memory foam. "
United States
Joshua K.
The price is NZ$1,138
includes taxes & fees
20 July - 21 July
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Amazing"
Sarahi 1-night trip
Posted 6 hours ago
Lime Tree Bay Resort

Find out more about Florida Keys

Florida Keys Holiday Homes information

Number of reviews
967
Accommodation
1077 Holiday Homes
Lowest Price
NZ$458
Highest Price
NZ$1,341