Search Vacation Homes in Fleming Key

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Our top choices for Fleming Key vacation homes

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is AED 1,098
AED 2,213 total
includes taxes & fees
2 Jun - 3 Jun
Paradise found

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
Private and Exclusive Florida Keys Getaway

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 2,808
AED 5,417 total
includes taxes & fees
18 May - 19 May
The Lighthouse - Beach Houses Key West

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 2,200
AED 5,350 total
includes taxes & fees
19 May - 20 May
Springtide 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 2,797
AED 5,828 total
includes taxes & fees
18 May - 19 May
Capmar House by Brightwild Huge Home Pool

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
The price is AED 2,200
AED 5,350 total
includes taxes & fees
18 May - 19 May
Capmar House at Lunara Bay

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (23 reviews)
"Great place and great hosts. However the pool never heated and couldn’t get anyone out to look at it. Overall an amazing stay and would definitely return."
United States
Austin S.
The price is AED 2,200
AED 5,350 total
includes taxes & fees
25 May - 26 May
The Seagate Estate at Lunara Bay

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, (22 reviews)
"Great spot , only a short drive downtown. Condo was excellent, clean and kept up beautifully. Had everything you needed and was a great place to spend the week"
United States
William H.
The price is AED 1,157
AED 3,631 total
includes taxes & fees
19 May - 20 May
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (13 reviews)
"The host was wonderfully responsive in the months leading up to our trip, and very helpful. The house was beautiful and exactly as pictured. Before we arrived, the host reached out and offered to pick up a grocery order from Publix for us - so nice!Any issues we experienced were minor and addressed in a timely manner. Key West was a ton of fun, even during a cold snap! Overall a wonderful stay!"
United States
ROHITA R.
The price is AED 2,200
AED 6,279 total
includes taxes & fees
19 May - 20 May
Altair House at Lunara Bay

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 1,219
AED 2,769 total
includes taxes & fees
24 May - 25 May
Starlight Serenity - Hideaway with Stunning Views

Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (63 reviews)
"This was a beautiful property, great location and awesome amenities. We loved it and will highly recommend it! "
United States
Kim H.
The price is AED 680
AED 1,192 total
includes taxes & fees
14 Jun - 15 Jun
Poolside Cottage #411

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 price is AED 3,374
AED 6,264 total
includes taxes & fees
2 Jun - 3 Jun
The Hemingway - Beach Houses Key West

The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AED 2,200
AED 6,512 total
includes taxes & fees
18 May - 19 May
The Shellstone House at Solaire Lunara Bay

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, (14 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is AED 679
AED 1,857 total
includes taxes & fees
14 Jun - 15 Jun
Road's End | Prime Old Town Location! Updated Home w/ Pool

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

Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"Location, pool, comfy beds. Will definitely return and recommend to others "
United States
janet n.
The price is AED 1,319
AED 2,520 total
includes taxes & fees
20 May - 21 May
Spacious 3-bedroom townhome on Stock Island with resort style pool.

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras
Old Town Key West
9.6 out of 10, Exceptional, (250 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is AED 559
AED 1,292 total
includes taxes & fees
18 May - 19 May
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
The price is AED 2,615
AED 6,842 total
includes taxes & fees
18 May - 19 May
Waterfront Luxury Home - Tidelands House

Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Easy checkin and checkout. Host quickly responded to any questions. Home was comfortable and provided an enjoyable and safe place to celebrate a birthday with girlfriends. "
United States
Debbie C.
The price is AED 2,200
AED 5,350 total
includes taxes & fees
18 May - 19 May
Spindrift House at Lunara Bay

Shared Pool & Near Duval - Curry House Room 9

Shared Pool & Near Duval - Curry House Room 9
Old Town Key West
7.4 out of 10, Good, (18 reviews)
"Very clean."
United States
Wendy R.
Shared Pool & Near Duval - Curry House Room 9
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