Fleming Key Vacation Rentals

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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 CA $409
CA $838 total
includes taxes & fees
Jun 2 - Jun 3
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.
The price is CA $787
CA $1,637 total
includes taxes & fees
May 26 - May 27
Private and Exclusive Florida Keys Getaway

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 CA $411
CA $997 total
includes taxes & fees
May 14 - May 15
Starlight Serenity - Hideaway with Stunning Views

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)
"Loved the quiet, well equipped, easy ride to all the activity in Key West. Enjoyed the French bakery and Italian restaurants within walking distance. Would most definitely return to this private townhouse....Thank you!"
United States
David M.
The price is CA $429
CA $1,348 total
includes taxes & fees
May 12 - May 13
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking

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 CA $680
CA $1,812 total
includes taxes & fees
May 11 - May 12
Springtide House at Lunara Bay

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 CA $1,045
CA $2,054 total
includes taxes & fees
May 12 - May 13
The Hemingway - Beach Houses Key West

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 CA $680
CA $1,812 total
includes taxes & fees
May 13 - May 14
The Seagate Estate at Lunara Bay

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 traveller
The price is CA $817
CA $1,986 total
includes taxes & fees
May 20 - May 21
Capmar House at Lunara Bay

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.
The price is CA $228
CA $419 total
includes taxes & fees
May 14 - May 15
Poolside Cottage #412

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 CA $682
CA $2,159 total
includes taxes & fees
May 10 - May 11
Altair 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 CA $961
CA $2,079 total
includes taxes & fees
May 19 - May 20
Capmar House by Brightwild Huge Home Pool

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 CA $1,092
CA $2,770 total
includes taxes & fees
May 19 - May 20
The Shellstone House at Solaire Lunara Bay

Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
Old Town Key West
8.8 out of 10, Excellent, (16 reviews)
"Very relaxing and tropical sitting on front porch "
United States
Dotti B.
The price is CA $461
CA $1,008 total
includes taxes & fees
May 11 - May 12
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl

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.
The price is CA $145
CA $434 total
includes taxes & fees
Jun 1 - Jun 2
Shared Pool & Near Duval - Curry House Room 9

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 CA $490
CA $941 total
includes taxes & fees
May 20 - May 21
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, (248 reviews)
"The condo/room was very clean and put together, the location is a nice neighborhood."
United States
Bonnie R.
The price is CA $208
CA $479 total
includes taxes & fees
May 19 - May 20
May Special 9-13 & 17 -19 & 29-1st 30$ off a ngt @169 lod + extras

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)
"Location, friendly neighbors, calming courtyard."
United States
Jim C.
The price is CA $279
CA $735 total
includes taxes & fees
May 11 - May 12
Road's End | Prime Old Town Location! Updated Home w/ Pool

Casita de Catherine by AvantStay | 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by AvantStay | 1 Block to Duval St w/ Hot Tub!
Old Town Key West
9.8 out of 10, Exceptional, (62 reviews)
"The amenities and location were great. "
United States
Tricia B.
Casita de Catherine by AvantStay | 1 Block to Duval St w/ Hot Tub!

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 CA $682
CA $1,813 total
includes taxes & fees
May 10 - May 11
Spindrift House at Lunara Bay

Gone Coastal

Gone Coastal
Stock Island
9.8 out of 10, Exceptional, (21 reviews)
"We only stayed at this home for one night. It is in a quiet neighborhood, The owner is very good about suggesting local restaurants. "
United States
Tina W.
The price is CA $409
CA $838 total
includes taxes & fees
May 31 - Jun 1
Gone Coastal
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

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Fleming Key Vacation Homes information

Number of reviews
614
Accommodation
736 Vacation Homes
Lowest Price
CA $419
Highest Price
CA $2,770

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