Fleming Key Vacation Rentals from ￥41,315: Search Short-Term Rentals

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Our top choices for Fleming Key vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

1. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

￥46,397 total

includes taxes & fees

Oct 30 - Oct 31

A pool area with a wooden deck, lounge chairs, and a waterfall feature.

2. Lighthouse Suites Collection

Old Town Key West

Melissa

￥118,926 total

includes taxes & fees

Nov 13 - Nov 14

A beachside resort with a wooden deck, palm trees, and a sunset view.

3. Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

￥95,938 total

includes taxes & fees

Oct 30 - Oct 31

A modern building with a concrete facade, a large window, and a gated entrance.

4. Contra House Key West

Old Town Key West

Rosalie

￥188,594 total

includes taxes & fees

Nov 9 - Nov 10

A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

5. The Grenada Suite Pool View Private Balcony

Key West

Luis

￥95,169 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with a wooden table and chairs, a blue sofa, and a view of the outdoors through a glass door.

6. Sunnyside Up by Brightwild Pool Parking

Old Town Key West

￥171,822 total

includes taxes & fees

Nov 22 - Nov 23

A covered porch with a table and chairs, overlooking a street with houses and cars.

7. Banana Split by Brightwild Pool Grill

Key West Historic District

￥94,373 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

8. The Bartlum Luxury Studio In Prime Location

Key West Historic District

￥107,658 total

includes taxes & fees

Nov 23 - Nov 24

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Top Fleming Key Hotel Reviews

Margaritaville Beach House Key West

10/10 Excellent

"The staff was very helpful and pleasant. They were eager to make your stay comfortable. Loved that there was a shuttle to and from the hotel from the airport. Also the shuttle to and from old town was a real bonus. Having the beach right across the street was fantastic."

Blue Flamingo Resort Key West

8/10 Good

"Their ad says shuttle service within 8 miles of the resort, but really the shuttle went to only 1 spot in town. Luckily, Uber is quick and relatively cheap. The restaurant on the property is OK, but nothing to write home about. Thank goodness for the Starbucks on site. If you don't mind loud music, then a poolside room is for you. If you prefer it a little quieter, then get a room overlooking the road. The elevators take FOREVER to arrive, and we took the stairs most of the time. Aside from those issues, it is a very nice place, and the staff were very friendly and helpful."

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Fantastic hotel. Spotless with great rooms. Nice pool and bar area . Breakfast was decent with plenty of choice. We eat in the restaurant twice and it was very good and reasonably priced. Hotel puts on a shuttle bus to downtown and the beach. Really recommend this hotel"

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Check prices for these dates

Our top choices for Fleming Key vacation rentals

1. Aqua Lodges at Hurricane Hole Marina

2. Lighthouse Suites Collection

3. Grand Marina Suite by Brightwild Waterfront

4. Contra House Key West

5. The Grenada Suite Pool View Private Balcony

6. Sunnyside Up by Brightwild Pool Parking

7. Banana Split by Brightwild Pool Grill

8. The Bartlum Luxury Studio In Prime Location

9. New The Cottage at James House

10. Duval Dream Loft by Brightwild Right on Duval

11. Capmar House by Brightwild Huge Home Pool

12. Tortuga Suite Sparkling Pool Hot Tub

13. Sky Suite on Duval by Brightwild Condo w Balcony

14. New Rose Petal Petite Suite - Pool Parking

15. Commodore s Cove by Brightwild Epic Location

16. Palmgale House in Key West

17. Suncoast House by Brightwild Pool Boat Dock

18. Sky Loft by Brightwild Penthouse in Prime Spot

19. New Waterfront Home - Sunray House

20. Mastway House by Brightwild Pool Dock

Find vacation rentals that suit your style

Top Fleming Key Hotel Reviews

Margaritaville Beach House Key West

Find out more about Fleming Key

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