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Fleming Key Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Fleming Key vacation homes

A kitchen with a refrigerator, stove, and two bar stools.

1. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Old Town Key West
9.0 out of 10, Wonderful, (198 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is CA $148
CA $397 total
includes taxes & fees
Aug 31 - Sep 1
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
A building with a red door, a covered porch, and a bamboo plant in the foreground.

2. 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
10.0 out of 10, Exceptional, (22 reviews)
"The property was very clean with an excellent location. "
United States
Mike T.
The price is CA $210
CA $642 total
includes taxes & fees
Aug 26 - Aug 27
Road's End | Prime Old Town Location! Updated Home w/ Pool
An aerial view of a beach with clear turquoise waters, a sandy shore, and a cluster of umbrellas.

3. Luxury two floor apartment in prime location of famous Duval Street

Luxury two floor apartment in prime location of famous Duval Street
Old Town Key West
9.6 out of 10, Exceptional, (103 reviews)
"Great stay at a great location. Apartment was very clean. Enjoyed the balcony overlooking Duval St. "
United States
Gregory L.
The price is CA $270
CA $822 total
includes taxes & fees
Aug 31 - Sep 1
Luxury two floor apartment in prime location of famous Duval Street
A wooden deck with a large tree, outdoor seating, and a marina in the background.

4. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is CA $230
CA $422 total
includes taxes & fees
Sep 1 - Sep 2
Poolside Cottage #412
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

5. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is CA $230
CA $422 total
includes taxes & fees
Aug 26 - Aug 27
Poolside Cottage #411
A pool area with a hot tub, outdoor seating, and a wooden fence with pool rules posted.

6. Private Parking, Heated Pool - Sweet Caroline

Private Parking, Heated Pool - Sweet Caroline
Key West Historic District
9.0 out of 10, Wonderful, (32 reviews)
"Parking was easy actually was easy. The location is great easy walking distance to Duval and everything that’s happening in downtown."
United States
Robert B.
The price is CA $345
CA $873 total
includes taxes & fees
Sep 1 - Sep 2
Private Parking, Heated Pool - Sweet Caroline
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

7. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (5 reviews)
"Nice place to stay! Highly recommend!"
United States
Mike C.
The price is CA $206
CA $383 total
includes taxes & fees
Aug 26 - Aug 27
One Bedroom Suite | Beachside Resort
A porch with wicker furniture and a white railing.

8. 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, (19 reviews)
"Great location!"
United States
Kayla S.
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

9. 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, (53 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $256
CA $1,032 total
includes taxes & fees
Aug 26 - Aug 27
Sea Esta Suite | Located On Iconic Duval w/ Pool
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

10. Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.0 out of 10, Wonderful, (6 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is CA $256
CA $853 total
includes taxes & fees
Aug 31 - Sep 1
Casa Havana | Old Town Condo w/ Pool & Balcony
A covered outdoor seating area with wicker furniture and a white table, overlooking a large tree and lush greenery.

11. 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 CA $346
CA $1,237 total
includes taxes & fees
Aug 27 - Aug 28
TORTUGA HAMMOCK -2 Bedroom/ 2.5 Bathroom Townhouse with Shared Pool & Parking
A swimming pool with a wooden deck, a covered patio area, and a building with large windows and a covered porch.

12. BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Key West Historic District
10.0 out of 10, Exceptional, (132 reviews)
"Great location to everything in Key West. Exactly as advertised."
United States
Jennifer B.
The price is CA $623
CA $1,716 total
includes taxes & fees
Sep 9 - Sep 10
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL

13. Keys Breeze - Walk to Duval, Private Pool

Keys Breeze - Walk to Duval, Private Pool
Old Town Key West
10.0 out of 10, Exceptional, (37 reviews)
"Great place, location, clean and climate controlled. Pool was great and the host was excellent!"
United States
Lisa S.
The price is CA $590
CA $1,440 total
includes taxes & fees
Aug 26 - Aug 27
Keys Breeze - Walk to Duval, Private Pool
An aerial view of a coastal area with clear turquoise waters, a sandy beach, and a small island with buildings and docks.

14. Steps to Duval •Hot tub • Sleeps 6

Steps to Duval •Hot tub • Sleeps 6
Old Town Key West
9.8 out of 10, Exceptional, (18 reviews)
"Perfect location parking is a plus and being put friendly as a plus"
United States
Kat B.
The price is CA $455
CA $884 total
includes taxes & fees
Aug 26 - Aug 27
Steps to Duval •Hot tub • Sleeps 6
A patio area with wicker furniture and a grill.

15. Southernmost Retreat | On Duval! With Hot Tub, Patio

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.8 out of 10, Exceptional, (32 reviews)
"Awesome place great location communication with host was great would stay here again next time I’m in key west."
United States
Drew L.
The price is CA $406
CA $1,300 total
includes taxes & fees
Sep 22 - Sep 23
Southernmost Retreat | On Duval! With Hot Tub, Patio

16. Coconut Palm - Steps from Duval with Private Pool

Coconut Palm - Steps from Duval with Private Pool
Old Town Key West
9.0 out of 10, Wonderful, (39 reviews)
"Great Property Excellent location "
United States
Jim B.
The price is CA $484
CA $1,264 total
includes taxes & fees
Sep 2 - Sep 3
Coconut Palm - Steps from Duval with Private Pool
A covered porch with two black chairs, a white door, and a palm tree in the background.

17. The Mesa House - One block from Duval St

The Mesa House - One block from Duval St
Key West Historic District
9.8 out of 10, Exceptional, (9 reviews)
"Perfect home for our family! The location was ideal for exploring Key West and enjoying the nightlife on Duval. The beds were comfortable and the kitchen had everything we needed. We will return!"
United States
Debbie P.
The price is CA $705
CA $1,594 total
includes taxes & fees
Sep 22 - Sep 23
The Mesa House - One block from Duval St
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

18. 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, (7 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is CA $374
CA $796 total
includes taxes & fees
Aug 29 - Aug 30
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A white building with blue shutters, surrounded by lush greenery and a brick pathway.

19. Passover Cottage | Private Pool & Ideal Key West Location

Passover Cottage | Private Pool & Ideal Key West Location
Old Town Key West
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful, clean property. Good location. Great stay, would absolutely stay again. Highly, recommended!!"
United States
john w.
The price is CA $576
CA $1,303 total
includes taxes & fees
Sep 7 - Sep 8
Passover Cottage | Private Pool & Ideal Key West Location
A wooden deck with two lounge chairs and a gazebo surrounded by lush greenery.

20. Atlantis House Suites

Atlantis House Suites
Midtown
10.0 out of 10, Exceptional, (3 reviews)
"Awesome place to stay ! Located just close enough and just far away enough . Highly recommended "
United States
Aaron J.
The price is CA $474
CA $1,098 total
includes taxes & fees
Aug 26 - Aug 27
Atlantis House Suites
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

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

8/10 Good
"Beach view, bar and restaurant. The staff was great"
Nairovys 2-night trip
Posted less than an hour ago
The Reach Key West, Curio Collection by Hilton

Find out more about Fleming Key

Fleming Key Vacation Homes information

Number of reviews
860
Accommodation
798 Vacation Homes
Lowest Price
CA $383
Highest Price
CA $1,716

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