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Fleming Key Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Fleming Key holiday rentals

2 bedrooms

1. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is HK$2,344
HK$4,544 total
includes taxes & fees
24 Aug - 25 Aug
Grand Marina Suite by Brightwild Waterfront
Exterior

2. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is HK$1,766
HK$4,207 total
includes taxes & fees
24 Aug - 25 Aug
Grand Marina Suite - Poolside & Waterfront Condo
Exterior

3. Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (34 reviews)
"Even more beautiful than the pictures! Everything was perfect. "
United States
Elizabeth K.
The price is HK$4,700
HK$11,398 total
includes taxes & fees
23 Aug - 24 Aug
Mastway House at Lunara Bay - Wellness Home
Pool

4. Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is HK$6,270
HK$14,756 total
includes taxes & fees
16 Aug - 17 Aug
Suncoast House at Lunara Bay
TV, offices

5. 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 HK$4,700
HK$11,383 total
includes taxes & fees
17 Aug - 18 Aug
Capmar House at Lunara Bay
TV, offices

6. 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
Elaine O.
The price is HK$4,700
HK$11,359 total
includes taxes & fees
16 Aug - 17 Aug
Waterlane House at Lunara Bay
Pool

7. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is HK$3,296
HK$4,171 total
includes taxes & fees
18 Aug - 19 Aug
Living the Dream Key West Style
Outdoor pool

8. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (39 reviews)
"Great stay and an excellent host! "
United States
Mike T.
The price is HK$1,373
HK$3,230 total
includes taxes & fees
18 Aug - 19 Aug
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Pool

9. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is HK$2,582
HK$5,198 total
includes taxes & fees
1 Sept - 2 Sept
Paradise found
Front of property

10. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (194 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is HK$770
HK$2,181 total
includes taxes & fees
13 Aug - 14 Aug
Aqua Lodges at Hurricane Hole Marina
Outdoor dining

11. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (68 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 HK$1,306
HK$2,391 total
includes taxes & fees
25 Aug - 26 Aug
Poolside Cottage #411
Outdoor dining

12. 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 HK$1,314
HK$2,407 total
includes taxes & fees
23 Aug - 24 Aug
Poolside Cottage #412
Exterior

13. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is HK$2,215
HK$4,142 total
includes taxes & fees
16 Aug - 17 Aug
Two Bedroom Residence With Balcony
Beach

14. Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Key West
9.0 out of 10, Wonderful, (138 reviews)
"Clean with very good furnishings."
United States
Allen J.
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Beach nearby, beach towels

15. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"Cute little place, host was very on top with communication."
United States
Michael L.
The price is HK$1,962
HK$3,238 total
includes taxes & fees
1 Sept - 2 Sept
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
2 bedrooms, iron/ironing board, WiFi, bed sheets

16. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The price is HK$1,091
HK$3,613 total
includes taxes & fees
31 Aug - 1 Sept
The Tortuga at Sunrise Suites - Balcony & Pool
Beach nearby

17. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.2 out of 10, Wonderful, (47 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is HK$1,962
HK$3,238 total
includes taxes & fees
1 Sept - 2 Sept
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Beach

18. Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Key West
9.0 out of 10, Wonderful, (144 reviews)
"Easy check in. Accommodations were very good as advertised. "
United States
Anonymous traveller
The price is HK$2,904
HK$3,675 total
includes taxes & fees
18 Aug - 19 Aug
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Beach nearby

19. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"We loved the location."
United States
Aneesah D.
The price is HK$4,429
HK$5,619 total
includes taxes & fees
14 Aug - 15 Aug
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Property grounds

20. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (46 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is HK$1,441
HK$4,049 total
includes taxes & fees
13 Aug - 14 Aug
The Cat Island Suite | Charmingly Renovated w/ Pool
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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"Well maintained vacation home"
Naveen 2-night trip
Posted 2 hours ago
Hyatt Vacation Club at Windward Pointe, Key West

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