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Popular destinations
Monroe County
Key West
Key Largo
Marathon
Lower Keys
Islamorada
Key Colony Beach
Sugarloaf Key
Tavernier
Layton (FL)
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What are you looking for in Florida keys?
Type anything e.g. Top rated villa with wifi and pool
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Popular filters
Vacation house
Vacation apartment
Pool
Pets allowed
WiFi
Balcony/Terrace
8.0
& higher
show all
Mesa House Uno by Brightwild Perfect Location
Key West
200 yd to the coast
Sleeps 4 pers.
1 bedroom
Balcony
Terrace
Kitchen
Internet
2 more units available
FREE cancellation
9.3
·
Fantastic
54 reviews
from
$295
per night
Best price:
TravelStaytion
More details
Sky Loft by Brightwild Penthouse in Prime Spot
Key West
600 yd to the coast
Sleeps 4 pers.
1 bedroom
Pool
Balcony
Terrace
Kitchen
FREE cancellation
9.5
·
Fantastic
23 reviews
from
$348
per night
Best price:
TravelStaytion
More details
Barefoot Bungalow~2 Bedroom, 2 Bathroom Home w/ Office, Pool and Tiki Hut!
Key West
500 yd to the coast
Sleeps 6 pers.
2 bedrooms
1,270 ft²
Yard
Terrace
Internet
FREE cancellation
9.7
·
Fantastic
12 reviews
from
$387
per night
Best price:
Vrbo
More details
Book on Vrbo
Ocean Front 3Br Presidential Suite
Key West
150 yd to the coast
Sleeps 8 pers.
3 bedrooms
Pool
Balcony
Terrace
Kitchen
FREE cancellation
9.6
·
Fantastic
from
$561
per night
Best price:
TravelStaytion
More details
Capmar House by Brightwild Huge Home Pool
Stock Island
0 yd to the coast
Sleeps 10 pers.
4 bedrooms
Balcony
Yard
Terrace
Parking
FREE cancellation
9.7
·
Fantastic
26 reviews
from
$1,053
per night
Best price:
TravelStaytion
More details
Seaport Sanctuary ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Key West
150 yd to the coast
Sleeps 4 pers.
1 bedroom
420 ft²
Pool
Terrace
Internet
FREE cancellation
8.7
·
Very good
3 reviews
from
$192
per night
Best price:
Vrbo
More details
Book on Vrbo
Seagate House by Brightwild Waterfront w Dock
Stock Island
0 yd to the coast
Sleeps 10 pers.
4 bedrooms
Balcony
Yard
Terrace
Parking
FREE cancellation
10
·
Fantastic
18 reviews
from
$1,053
per night
Best price:
TravelStaytion
More details
Island View 1Br Residence with Balcony
Key West
150 yd to the coast
Sleeps 4 pers.
1 bedroom
Pool
Balcony
Terrace
Kitchen
3 more units available
FREE cancellation
10
·
Fantastic
2 reviews
from
$234
per night
Best price:
TravelStaytion
More details
The Bartlum Luxury Studio In Prime Location
Key West
250 yd to the coast
Sleeps 4 pers.
1 bedroom
Balcony
Terrace
Kitchen
Internet
FREE cancellation
9.5
·
Fantastic
33 reviews
from
$302
per night
Best price:
TravelStaytion
More details
Waterfront retreat with balcony views, kayak, Sup, central Ac & washer/dryer
Duck Key
30 yd to the coast
Sleeps 6 pers.
2 bedrooms
775 ft²
Balcony
Yard
Parking
Internet
FREE cancellation
8.4
·
Very good
53 reviews
from
$298
per night
Best price:
Vrbo
More details
Book on Vrbo
The Trinidad by Brightwild Pool View Parking
Key West
450 yd to the coast
Sleeps 6 pers.
2 bedrooms
Pool
Balcony
Terrace
Parking
FREE cancellation
10
·
Fantastic
from
$406
per night
Best price:
TravelStaytion
More details
Colony Calypso - A quaint 1 Bedroom Cottage just two blocks to Duval
Key West
850 yd to the coast
Sleeps 4 pers.
1 bedroom
517 ft²
Pool
Yard
Terrace
Internet
FREE cancellation
9.4
·
Fantastic
56 reviews
from
$504
per night
Best price:
Vrbo
More details
Book on Vrbo
Mirador House by Brightwild Pool Dock
Stock Island
10 yd to the coast
Sleeps 16 pers.
5 bedrooms
Balcony
Terrace
Parking
Kitchen
FREE cancellation
9.4
·
Fantastic
27 reviews
from
$1,711
per night
Best price:
TravelStaytion
More details
Resort View 1Br Suite
Key West
150 yd to the coast
Sleeps 4 pers.
1 bedroom
Pool
Balcony
Terrace
Kitchen
3 more units available
FREE cancellation
8.9
·
Very good
3 reviews
from
$234
per night
Best price:
TravelStaytion
More details
Poolside Retreat by Brightwild Cottage w Pool
Key West
700 yd to the coast
Sleeps 4 pers.
1 bedroom
Pool
Balcony
Yard
Terrace
One more unit available
FREE cancellation
8.9
·
Very good
40 reviews
from
$436
per night
Best price:
TravelStaytion
More details
Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
20 yd to the coast
Sleeps 4 pers.
2 bedrooms
850 ft²
Yard
Terrace
Parking
Internet
FREE cancellation
8.6
·
Very good
146 reviews
from
$411
per night
Best price:
Vrbo
More details
Book on Vrbo
Aquaria House at Lunara Bay
Stock Island
40 yd to the coast
Sleeps 10 pers.
4 bedrooms
2,325 ft²
Pool
Balcony
Parking
Internet
FREE cancellation
9.8
·
Fantastic
27 reviews
from
$1,536
per night
Best price:
Vrbo
More details
Book on Vrbo
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
50 yd to the coast
Sleeps 4 pers.
2 bedrooms
743 ft²
Terrace
Parking
Internet
FREE cancellation
8.0
·
Very good
43 reviews
from
$456
per night
Best price:
Vrbo
More details
Book on Vrbo
Perfect little paradise spot in key largo Florida. (lot 15)
Key Largo
10 yd to the coast
Sleeps 6 pers.
2 bedrooms
549 ft²
Pool
Parking
Internet
FREE cancellation
9.1
·
Fantastic
25 reviews
from
$223
per night
Best price:
Vrbo
More details
Book on Vrbo
Private and Exclusive Beach Getaway
Sugarloaf Key
60 yd to the coast
Sleeps 8 pers.
3 bedrooms
2,303 ft²
Balcony
Yard
Parking
Internet
FREE cancellation
8.0
·
Very good
2 reviews
from
$3,220
per night
Best price:
Vrbo
More details
Book on Vrbo
Exclusive Key West Beach Front - 2Br Luxury Condo w/Gym and Pool Access (Newly Refurnished!)
Key West
30 yd to the coast
Sleeps 6 pers.
2 bedrooms
1,894 ft²
Pool
Balcony
Parking
Internet
9.1
·
Fantastic
36 reviews
from
$750
per night
Best price:
Vrbo
More details
Book on Vrbo
Mermaid Manor Waterfront Haven w Hot Tub Dock
Marathon
20 yd to the coast
Sleeps 10 pers.
4 bedrooms
Balcony
Yard
Terrace
Parking
FREE cancellation
from
$406
per night
Best price:
TravelStaytion
More details
Spindrift House by Brightwild Huge Pool Dock
Stock Island
10 yd to the coast
Sleeps 12 pers.
4 bedrooms
Balcony
Terrace
Parking
Kitchen
FREE cancellation
9.8
·
Fantastic
25 reviews
from
$1,053
per night
Best price:
TravelStaytion
More details
Islamorada retreat \"Bungalow Blue\" w/ heated pool, Bikes, Bbq, amenities galore!
Islamorada
70 yd to the coast
Sleeps 4 pers.
2 bedrooms
517 ft²
Pool
Hot tub
Parking
Internet
FREE cancellation
10
·
Fantastic
18 reviews
from
$455
per night
Best price:
Vrbo
More details
Book on Vrbo
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
Key Largo
150 yd to the coast
Sleeps 8 pers.
3 bedrooms
Hot tub
Balcony
Parking
Internet
FREE cancellation
9.9
·
Fantastic
83 reviews
from
$527
per night
Best price:
Vrbo
More details
Book on Vrbo
Sky Suite on Duval by Brightwild Condo w Balcony
Key West
700 yd to the coast
Sleeps 6 pers.
2 bedrooms
Balcony
Terrace
Parking
Kitchen
One more unit available
FREE cancellation
9.8
·
Fantastic
48 reviews
from
$650
per night
Best price:
TravelStaytion
More details
Sugar Palm Studio ~ Adult Only Studio w/ Community Pool & Close to Town!
Key West
600 yd to the coast
Sleeps 2 pers.
1 bedroom
248 ft²
Pool
Yard
Terrace
Parking
5 more units available
FREE cancellation
9.6
·
Fantastic
314 reviews
from
$590
per night
Best price:
Vrbo
More details
Book on Vrbo
Hawks Cay Resort
Duck Key
30 yd to the coast
Sleeps 2 pers.
1 bedroom
1,227 ft²
Pool
Sauna
Balcony
Parking
9 more units available
FREE cancellation
from
$337
per night
Best price:
Leavetown
More details
Isla Bella Beach Resort
Marathon
60 yd to the coast
Sleeps 4 pers.
1 bedroom
1,798 ft²
Pool
Balcony
Parking
Internet
9 more units available
FREE cancellation
from
$342
per night
Best price:
Leavetown
More details
New Pricing: Drive To Your Getaway - Big Pool, Steps to Beach & Free Parking
Key West
150 yd to the coast
Sleeps 12 pers.
5 bedrooms
2,691 ft²
Pool
Balcony
Yard
Parking
FREE cancellation
9.8
·
Fantastic
92 reviews
from
$1,893
per night
Best price:
Vrbo
More details
Book on Vrbo
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