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Our top choices for Fleming Key vacation homes

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is AED 830
AED 2,324 total
includes taxes & fees
1 Jul - 2 Jul
Starlight Serenity - Hideaway with Stunning Views

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 AED 1,221
AED 2,669 total
includes taxes & fees
1 Jul - 2 Jul
Starlight Serenity - Hideaway w Stunning Views

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.
Paradise found

One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (4 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is AED 694
AED 1,191 total
includes taxes & fees
28 Jun - 29 Jun
One Bedroom Suite | Beachside Resort

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras
Old Town Key West
9.6 out of 10, Exceptional, (251 reviews)
"Loved our stay here!"
United States
Kristin E.
The price is AED 479
AED 1,192 total
includes taxes & fees
2 Jul - 3 Jul
Summer special@ 129 Sun thru Wed.ngts lodging only 129 + extras

Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (2 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is AED 843
AED 1,907 total
includes taxes & fees
28 Jun - 29 Jun
Slice of Paradise

Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (31 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is AED 612
AED 1,126 total
includes taxes & fees
1 Jul - 2 Jul
Poolside Cottage #412

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 AED 654
AED 1,845 total
includes taxes & fees
24 Jul - 25 Jul
Road's End | Prime Old Town Location! Updated Home w/ Pool

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
10.0 out of 10, Exceptional, (23 reviews)
"Great place nice and clean easy access to the pool short drive to the beach"
United States
Nathan W.
The price is AED 1,194
AED 3,679 total
includes taxes & fees
30 Jun - 1 Jul
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

The Lighthouse - Beach Houses Key West

The Lighthouse - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (11 reviews)
"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"
United States
Peter Q.
The price is AED 3,212
AED 5,726 total
includes taxes & fees
13 Jul - 14 Jul
The Lighthouse - Beach Houses Key West

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (28 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is AED 3,184
AED 6,549 total
includes taxes & fees
7 Jul - 8 Jul
Evershore Estate at Lunara Bay | Wellness Home

Luxurious Island Pearl-Private Pool - 2BD/2Bath

Luxurious Island Pearl-Private Pool - 2BD/2Bath
Key West Historic District
10.0 out of 10, Exceptional, (56 reviews)
"Amazing stay five star!! "
United States
Erica S.
The price is AED 1,844
AED 3,869 total
includes taxes & fees
11 Jul - 12 Jul
Luxurious Island Pearl-Private Pool - 2BD/2Bath

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The Hemingway - Beach Houses Key West

Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (47 reviews)
"Great stay! "
United States
Colleen S.
The price is AED 1,043
AED 3,216 total
includes taxes & fees
7 Jul - 8 Jul
Sea Esta Suite | Located On Iconic Duval w/ Pool

Crestwood House at Lunara Bay

Crestwood House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (2 reviews)
"The house and property was perfect for 4 adults and 4 kids. Gourmet kitchen for great breakfasts to start the day. Grill for cookouts and swimming in the early evenings. Good proximity to downtown key west, but far enough away for quiet time. Would stay again."
United States
Vicki L.
Crestwood House at Lunara Bay

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is AED 3,424
AED 6,443 total
includes taxes & fees
28 Jun - 29 Jun
Capmar House by Brightwild Huge Home Pool

Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great host!"
United States
Mario C.
Spindrift House at Lunara Bay

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
The price is AED 3,937
AED 7,551 total
includes taxes & fees
26 Jul - 27 Jul
Capmar House at Lunara Bay

Springtide House at Lunara Bay

Springtide House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is AED 3,140
AED 6,496 total
includes taxes & fees
30 Jun - 1 Jul
Springtide House at Lunara Bay

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Had to book here last minute due to first booking being canceled night before check-in! What a great experience this was. Host was very easy to deal with and would respond back very quickly. Even willing to let is get in a little early due to our situation. Glad we booked here! ALSO the house and property are great! Very well maintained and clean! "
United States
Matt P.
Suncoast House at Lunara Bay
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 Fleming Key Hotel Reviews