Default HTG hotel image

Fleming Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Fleming Key vacation homes

A wooden deck with a large tree, outdoor seating, and a marina in the background.

1. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is CA $235
CA $434 total
includes taxes & fees
Oct 25 - Oct 26
Poolside Cottage #412
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

2. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
The price is CA $235
CA $434 total
includes taxes & fees
Oct 20 - Oct 21
Poolside Cottage #411
A patio area with a fountain, seating, and umbrellas.

3. Andros Suite | Perfect Location with Pool!

Andros Suite | Perfect Location with Pool!
Old Town Key West
10.0 out of 10, Exceptional, (5 reviews)
"Great little place 1 block off Duval. A nice quiet oasis from everything a street away. Moon Dog restaurant is around the block and was great for breakfast and dinner. Great kitchen! The mattress upstairs could use a firmer replacement IMHO…overall very good spot!"
United States
Robert J.
The price is CA $201
CA $639 total
includes taxes & fees
Nov 2 - Nov 3
Andros Suite | Perfect Location with Pool!
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with bar stools.

4. 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, (56 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is CA $263
CA $1,057 total
includes taxes & fees
Oct 29 - Oct 30
Sea Esta Suite | Located On Iconic Duval w/ Pool
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

5. One Bedroom Suite | Beachside Resort

One Bedroom Suite | Beachside Resort
Key West
10.0 out of 10, Exceptional, (8 reviews)
"Great property, room was amazing!"
United States
Daris Y.
The price is CA $239
CA $428 total
includes taxes & fees
Oct 27 - Oct 28
One Bedroom Suite | Beachside Resort
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

6. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is CA $337
CA $787 total
includes taxes & fees
Oct 20 - Oct 21
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Living Area

7. 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 CA $847
CA $2,060 total
includes taxes & fees
Oct 25 - Oct 26
Capmar House at Lunara Bay
A white two-story house with a balcony and a swimming pool.

8. 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 $1,086
CA $2,202 total
includes taxes & fees
Oct 25 - Oct 26
Capmar House by Brightwild Huge Home Pool
A clear swimming pool with lounge chairs and palm trees.

9. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (4 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
The price is CA $355
CA $810 total
includes taxes & fees
Oct 20 - Oct 21
Slice of Paradise
An aerial view of a beach with clear turquoise waters, a sandy shore, and a dense forested area.

10. 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 $417
CA $1,021 total
includes taxes & fees
Oct 26 - Oct 27
Luxury two floor apartment in prime location of famous Duval Street
A clear swimming pool surrounded by palm trees and lounge chairs, with a building in the background.

11. 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, (8 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 $382
CA $842 total
includes taxes & fees
Oct 20 - Oct 21
Spacious 3-bedroom townhome on Stock Island with resort style pool.
A living room with a beige sofa, a white coffee table with a plant, and a view through glass doors to an outdoor area.

12. Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
United States
Justin S.
The price is CA $847
CA $2,060 total
includes taxes & fees
Oct 20 - Oct 21
Waterlane House at Lunara Bay
Pool Deck with Lounge Chairs

13. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (29 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is CA $847
CA $2,060 total
includes taxes & fees
Oct 20 - Oct 21
The Seagate Estate at Lunara Bay
Property Overview

14. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
The price is CA $847
CA $2,060 total
includes taxes & fees
Oct 20 - Oct 21
Aquaria House at Lunara Bay
Pool Deck with Lounge Chairs

15. Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is CA $847
CA $2,301 total
includes taxes & fees
Oct 20 - Oct 21
Suncoast House at Lunara Bay
A wooden deck with a hanging hammock and a view of a green landscape.

16. 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 $322
CA $892 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway with Stunning Views
A covered porch with a table and chairs, a view of the street, and a building with a balcony.

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

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is CA $324
CA $963 total
includes taxes & fees
Nov 16 - Nov 17
Casa Havana | Old Town Condo w/ Pool & Balcony
A white two-story house with a central archway and a paved driveway.

18. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is CA $1,449
CA $2,966 total
includes taxes & fees
Oct 25 - Oct 26
Palmgale House in Key West
Property Overview

19. Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (35 reviews)
"Property was good would stay here again!"
United States
Richard K.
The price is CA $847
CA $2,060 total
includes taxes & fees
Oct 20 - Oct 21
Spindrift House at Lunara Bay
A patio area with wicker furniture and a grill.

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

Southernmost Retreat | On Duval! With Hot Tub, Patio
Old Town Key West
9.6 out of 10, Exceptional, (34 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 $417
CA $1,343 total
includes taxes & fees
Oct 20 - Oct 21
Southernmost Retreat | On Duval! With Hot Tub, Patio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"It was my first time to Key West with friends and we didnt know where to stay but we are glad we choose the Blue Flamingo. We had a late arrival from Miami and checked in about 130am which was quick and easy. Our room was clean, comfy beds, great AC 👌 since we were exhausted from traveling. We stayed 3 nights and enjoyed the pool. This location had security on-site for the parking lot also. We felt safe at night. I liked the scent of the front lobby. We didnt get a chance to enjoy any of the restaurants on property. We have no complaints and I would return."
Andrea 3-night trip
Posted 4 hours ago
Blue Flamingo Resort Key West

Find out more about Fleming Key

Fleming Key Vacation Homes information

Number of reviews
534
Accommodation
798 Vacation Homes
Lowest Price
CA $428
Highest Price
CA $2,966

Explore a world of travel with Expedia