Fleming Key Vacation Homes

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Our top choices for Fleming Key holiday homes

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

1. Poolside Cottage #412

Key West

shannon b.

HK$2,376 total

includes taxes & fees

25 Oct - 26 Oct

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

2. Poolside Cottage #411

Key West

Cristy D.

HK$2,376 total

includes taxes & fees

20 Oct - 21 Oct

A patio area with a fountain, seating, and umbrellas.

3. Andros Suite | Perfect Location with Pool!

Old Town Key West

Robert J.

HK$3,544 total

includes taxes & fees

2 Nov - 3 Nov

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

Old Town Key West

Rick H.

HK$5,840 total

includes taxes & fees

29 Oct - 30 Oct

A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

5. One Bedroom Suite | Beachside Resort

Key West

Daris Y.

HK$2,369 total

includes taxes & fees

27 Oct - 28 Oct

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

Stock Island

Linda

HK$4,097 total

includes taxes & fees

20 Oct - 21 Oct

7. Capmar House at Lunara Bay

Raccoon Key

Wilbert C.

HK$11,432 total

includes taxes & fees

25 Oct - 26 Oct

A white two-story house with a balcony and a swimming pool.

8. Capmar House by Brightwild Huge Home Pool

Raccoon Key

Karen

HK$12,221 total

includes taxes & fees

25 Oct - 26 Oct

A clear swimming pool with lounge chairs and palm trees.

9. Slice of Paradise

Stock Island

Cathy S.

HK$4,438 total

includes taxes & fees

20 Oct - 21 Oct

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

Old Town Key West

Gregory L.

HK$5,629 total

includes taxes & fees

26 Oct - 27 Oct

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.

Stock Island

Samantha P.

HK$4,621 total

includes taxes & fees

20 Oct - 21 Oct

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

Raccoon Key

Justin S.

HK$11,432 total

includes taxes & fees

20 Oct - 21 Oct

13. The Seagate Estate at Lunara Bay

Raccoon Key

Jason T.

HK$11,432 total

includes taxes & fees

20 Oct - 21 Oct

14. Aquaria House at Lunara Bay

Raccoon Key

Chris H.

HK$11,432 total

includes taxes & fees

20 Oct - 21 Oct

15. Suncoast House at Lunara Bay

Raccoon Key

carlos s.

HK$12,773 total

includes taxes & fees

20 Oct - 21 Oct

A wooden deck with a hanging hammock and a view of a green landscape.

16. Starlight Serenity - Hideaway with Stunning Views

Summerland Key

Tom H.

HK$4,975 total

includes taxes & fees

27 Oct - 28 Oct

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

Old Town Key West

Kim T.

HK$5,375 total

includes taxes & fees

16 Nov - 17 Nov

A white two-story house with a central archway and a paved driveway.

18. Palmgale House in Key West

Raccoon Key

HK$16,463 total

includes taxes & fees

25 Oct - 26 Oct

19. Spindrift House at Lunara Bay

Raccoon Key

Richard K.

HK$11,432 total

includes taxes & fees

20 Oct - 21 Oct

A patio area with wicker furniture and a grill.

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

Old Town Key West

Drew L.

HK$7,380 total

includes taxes & fees

20 Oct - 21 Oct

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Top Fleming Key Hotel Reviews

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."

Havana Cabana at Key West

10/10 Excellent

"My boyfriend and I went to this resort as part of his birthday plans and we had a great time. The resort’s theme was nice, music was a vibe (Latin), and everything was very clean. The food truck they have by the pool was a great spot to hit for breakfast and lunch as for convenience (can be a pricey, like the bars). We went to Duval street at night and got practically the same drinks (margs) for literally half the price. We had a great time during the day lounging by the pool - the water can be cold, but there’s a steamy hot tub too. It wasn’t too packed (could be because it was October). We had parking right in front of our room where we stayed. A fire alarm did go off at 3 am and woke us up out of our sleep and dragged us outside. I overhead a man saying this happens almost nightly, but we did not have it happen to us on night 2/2 of our stay. Hotel is at a great spot, next to Publix and some other stores, and across the water which has a great view and boardwalk. The free shuttle to and from the city was amazing, but it does end at 10:30 pm, so if you like to party late you’ll probably have to catch a paid driver back. Pet friendly and they had treats for the doggie in the lobby! Overall, we had a great stay and I’d come back!"

The Southernmost Inn - Adults Only

10/10 Excellent

"We had an amazing stay. Check in was easy and everyone on the property was helpful and friendly. Our room was clean and comfortable and loved the updated bathroom. Loved the private pool and happy hour complete with visits from wildlife. It was in a wonderful location but far enough away from any loud craziness. Overall no complaints"

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