Search Vacation Homes in Fleming Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Fleming Key vacation homes

Starlight Serenity - Hideaway with Stunning Views

Vacation Home in Upper Sugarloaf Key

Private and Exclusive Florida Keys Getaway
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is AED 4,020
AED 6,904 total
includes taxes & fees
24 Mar - 25 Mar
Private and Exclusive Florida Keys Getaway

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
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 2,935
AED 6,246 total
includes taxes & fees
9 Mar - 10 Mar
Capmar House at Lunara Bay

Vacation Home in Raccoon Key

Springtide House at Lunara Bay
9.6 out of 10, Exceptional, (44 reviews)
"It was great. House was amazing"
United States
Ernest H.
The price is AED 2,935
AED 6,279 total
includes taxes & fees
8 Mar - 9 Mar
Springtide House at Lunara Bay

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (22 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is AED 2,935
AED 6,279 total
includes taxes & fees
8 Mar - 9 Mar
The Seagate Estate at Lunara Bay

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is AED 1,611
AED 3,119 total
includes taxes & fees
31 Mar - 1 Apr
Starlight Serenity - Hideaway w Stunning Views

Vacation Home in Upper Sugarloaf Key

The Hemingway - Beach Houses Key West
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 5,232
AED 8,626 total
includes taxes & fees
11 Mar - 12 Mar
The Hemingway - Beach Houses Key West

Vacation Home in Raccoon Key

Altair House at Lunara Bay
9.8 out of 10, Exceptional, (13 reviews)
"Great house. Large space, everything you need is there. "
United States
CRIMSON A.
The price is AED 4,117
AED 8,708 total
includes taxes & fees
8 Mar - 9 Mar
Altair House at Lunara Bay

Vacation Home in Raccoon Key

The Shellstone House at Solaire Lunara Bay
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home with great outdoor space and we loved the pool and private dock"
United States
Sharon L.
The price is AED 4,771
AED 9,772 total
includes taxes & fees
8 Mar - 9 Mar
The Shellstone House at Solaire Lunara Bay

Vacation Home in Sugarloaf Key

Private and Exclusive Beach Getaway
10.0 out of 10, Exceptional, (10 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is AED 3,030
AED 5,813 total
includes taxes & fees
9 Mar - 10 Mar
Private and Exclusive Beach Getaway
9.6 out of 10, Exceptional, (243 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is AED 955
AED 1,793 total
includes taxes & fees
11 Mar - 12 Mar
Close to all & beach with your own full front porch ,full kitchen good rates

Vacation Home in Upper Sugarloaf Key

The Lighthouse - Beach Houses Key West
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 4,040
AED 6,987 total
includes taxes & fees
4 Apr - 5 Apr
The Lighthouse - Beach Houses Key West
9.8 out of 10, Exceptional, (27 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 2,935
AED 6,279 total
includes taxes & fees
8 Mar - 9 Mar
Evershore Estate at Lunara Bay | Wellness Home

Vacation Home in Old Town Key West

Shared Pool & Near Duval - Curry House Room 9
7.4 out of 10, Good, (16 reviews)
"Very clean."
United States
Wendy R.
The price is AED 702
AED 1,565 total
includes taxes & fees
12 Mar - 13 Mar
Shared Pool & Near Duval - Curry House Room 9
9.0 out of 10, Wonderful, (250 reviews)
"It was somewhat dated, but clean and a fantastic location! Loved the garden area and the fact that it was secure with a gate combination and a bungalow combination to get in."
United States
Donna W.
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown

Vacation Home in Raccoon Key

Capmar House by Brightwild Huge Home Pool
2.0 star property
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 3,620
AED 6,687 total
includes taxes & fees
9 Mar - 10 Mar
Capmar House by Brightwild Huge Home Pool
10.0 out of 10, Exceptional, (17 reviews)
"This property was very clean and comfortable. I would definitely stay here again. The pool was very nice "
United States
L G.
The price is AED 1,653
AED 4,196 total
includes taxes & fees
8 Mar - 9 Mar
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
8.6 out of 10, Excellent, (13 reviews)
"This place was great!!! Location was walking distance to everything. The pool was amazing , it felt like our own little resort. We enjoyed having coffee on the patio and watching the birds and iguanas in the trees. "
United States
keri c.
The price is AED 1,130
AED 2,544 total
includes taxes & fees
31 Mar - 1 Apr
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
9.8 out of 10, Exceptional, (7 reviews)
"First class, attentive customer service. Prime location. Attractive setting. Easy access. Complimentary airport transportation. "
United States
Cynthia
The price is AED 1,164
AED 2,484 total
includes taxes & fees
10 Mar - 11 Mar
Road's End | Prime Old Town Location! Updated Home w/ Pool
9.4 out of 10, Exceptional, (49 reviews)
"We thoroughly enjoyed our stay and found the communication back-and-forth with Joe to be efficient and easy, thank you for a great stay!"
United States
Elizabeth W.
The price is AED 1,322
AED 3,533 total
includes taxes & fees
14 Mar - 15 Mar
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
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.

Eid al-Fitr Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Fleming Key Hotel Reviews