Saddlebunch Keys Holiday Rentals, Florida: Private House Rentals

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Our top choices for Saddlebunch Keys hotels

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A bar area with a thatched roof, wooden chairs, and a poolside view.

A hotel room with a balcony, a bed, a desk, and two chairs.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

1. Hampton Inn Key West FL

Key West

Erika

4.372.537 ₫

4.919.105 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with boats docked, a swimming pool, and palm trees.

2. The Perry Hotel & Marina Key West

Stock Island

Jade

3.620.836 ₫

5.669.743 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

A modern office space with a reception desk, computer, and seating area.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

3. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

Brian

3.236.712 ₫

4.368.850 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A marina with boats docked, a pool area, and a building with a white facade.

A breakfast setting with a table, chairs, a vase with flowers, and a city view.

A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

A clear view of turquoise ocean water and a blue sky with clouds.

4. Hilton Key West Resort & Marina

Stock Island

Eric A

3.167.750 ₫

5.078.460 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A balcony with a view of a pool area, palm trees, and outdoor seating.

A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.

A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.

5. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

3.084.062 ₫

4.342.784 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

A couple holding hands in a tropical setting with palm trees and greenery.

6. Blue Flamingo Resort Key West

New Town

Esteban

3.239.214 ₫

5.100.596 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A dining table with plates of food, a drink, and a view of a pool and palm trees.

A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

A person standing by a window overlooking a beach with palm trees and the ocean.

7. Margaritaville Beach House Key West

Key West

Richard

5.049.135 ₫

7.310.079 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A swimming pool with lounge chairs and palm trees.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

A modern living room with a sectional sofa, a small round table, and a potted plant.

8. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

2.744.090 ₫

3.814.908 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

9. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

4.498.797 ₫

5.061.146 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

10. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

4.990.254 ₫

6.779.220 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A tall palm tree with a white building in the background.

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

11. Parrot Key Hotel & Villas

Northside Resort

Anthony

3.935.736 ₫

5.913.442 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A swimming pool surrounded by palm trees and a natural rock formation.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

A covered outdoor seating area with a pool in the background.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

12. Havana Cabana at Key West

New Town

Stephanie

3.751.585 ₫

5.863.727 ₫ total

includes taxes & fees

1 Nov - 2 Nov

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

A spacious living area with a large window, a dining table, and comfortable seating.

13. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

6.133.534 ₫

8.065.411 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A modern dining area with a glass table, four chairs, and a ceiling fan.

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

A beach with palm trees, clear blue water, and a pier extending into the sea.

14. Beachside Resort & Residences

Key West

Mollie

3.028.916 ₫

5.883.549 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A waterfront building with a flat roof, large windows, and a balcony.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

15. Sugar Loaf Lodge

Summerland Key

morgan

3.078.887 ₫

3.463.877 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A beach with a wooden pier, palm trees, and beach umbrellas.

A modern bar area with a central island, white bar stools, and a view of the ocean.

An outdoor dining area with tables and chairs, overlooking the ocean.

A resort with a pool, lounge chairs, umbrellas, palm trees, and a view of the ocean.

16. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

3.939.620 ₫

6.179.851 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.

A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

A multi-story hotel with balconies and a well-lit entrance.

17. The Laureate Key West

New Town

Eileen

4.113.807 ₫

5.355.969 ₫ total

includes taxes & fees

20 Oct - 21 Oct

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

A spacious lobby with green sofas, a coffee table, and a dining area.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

18. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Charlene

5.585.981 ₫

8.030.656 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

A marina with boats docked, a beach resort building, and palm trees.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

19. Ibis Bay Beach Resort

Northside Resort

Andre

3.523.519 ₫

4.799.267 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A hotel with a swimming pool, balconies, and a view of the sea.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

A balcony with a view of the ocean, a table, chairs, and a railing.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

20. Hyatt Centric Key West Resort and Spa

Key West Historic District

Jennifer

6.188.427 ₫

8.768.017 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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Top Saddlebunch Keys Hotel Reviews

The Southernmost Inn - Adults Only

10/10 Excellent

"Very clean, nice pool and hot tub, basic breakfast and simple happy hour, complimentary wine. Extremely friendly staff."

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent

"Amazing stay! Would highly recommend!"

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent

"Unable to understand with the staff on my arrival. It was so frustrating!! Other than that nice atmosphere."

Parrot Key Hotel & Villas

8/10 Good

"Pretty spot with shuttle service to town. Pools are nice, but no beach access. Restaurant was being remodeled, and a food truck was on-site all day with breakfast and lunch or light dinner options. Super friendly and helpful staff!"

Beachside Resort & Residences

10/10 Excellent

"We were very happy with how nice, clean and comfortable our 1 bedroom was. The staff was very helpful via text messages for anything we needed like coffee. The pool was clean and well kept. The shuttle bus to Duval street was a very pleasant surprise and the drivers were really prompt."

Pier House Resort & Spa

8/10 Good

"The location of the property was great for our visit because we had a couple of excursions from the pier not too far. The property was really nice and we enjoyed having the beach to be able to get in the ocean after a hot day. Food and drinks at the hotel were great. The only complaint I have is in our room there was only 1 tabletop lamp and only one in the sitting area so it was real hard to see when trying to get ready with 4 people. Even the bathroom light wasn’t very bright. I would stay here again."

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"Great property"

Margaritaville Beach House Key West

10/10 Excellent

"It is such a convenient location and beautiful place to stay. Beds are comfy! Wish they had a little more to offer on their menu though."

Havana Cabana at Key West

10/10 Excellent

"pool was the best with food and bar right next. shuttle service to town was excellent can't wait to go back!"

More cheap stays in Saddlebunch Keys

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

3.523.519 ₫

4.799.267 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

3.599.127 ₫

4.922.906 ₫ total

26 Oct - 27 Oct

includes taxes & fees

Parmer's Resort

565 Barry Avenue Summerland Key FL

3.796.171 ₫

5.115.582 ₫ total

3 Nov - 4 Nov

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

4.631.267 ₫

5.210.175 ₫ total

26 Oct - 27 Oct

includes taxes & fees

Pegasus International Hotel

501 Southard Street Key West FL

4.401.810 ₫

6.262.869 ₫ total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,002 reviews)

Alexander Palms Court

715 South St Key West FL

5.821.425 ₫

6.549.232 ₫ total

19 Oct - 20 Oct

includes taxes & fees

9.4/10 Exceptional! (1,005 reviews)

Find hotels in Saddlebunch Keys, FL from 3.463.877 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Saddlebunch Keys

Check prices for these dates

Filter by

Star rating

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Our top choices for Saddlebunch Keys hotels

1. Hampton Inn Key West FL

2. The Perry Hotel & Marina Key West

3. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

4. Hilton Key West Resort & Marina

5. DoubleTree Resort by Hilton Grand Key - Key West

6. Blue Flamingo Resort Key West

7. Margaritaville Beach House Key West

8. Hilton Garden Inn Key West / The Keys Collection

9. Courtyard by Marriott Key West Waterfront

10. Hyatt Vacation Club at Windward Pointe, Key West

11. Parrot Key Hotel & Villas

12. Havana Cabana at Key West

13. Hyatt Vacation Club at Beach House, Key West

14. Beachside Resort & Residences

15. Sugar Loaf Lodge

16. The Reach Key West, Curio Collection by Hilton

17. The Laureate Key West

18. Casa Marina Key West, Curio Collection by Hilton

19. Ibis Bay Beach Resort

20. Hyatt Centric Key West Resort and Spa

Top Saddlebunch Keys Hotel Reviews

The Southernmost Inn - Adults Only

Winslow's Bungalows - Key West Historic Inns

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Parrot Key Hotel & Villas

Beachside Resort & Residences

Pier House Resort & Spa

Casa Marina Key West, Curio Collection by Hilton

Margaritaville Beach House Key West

Havana Cabana at Key West

More cheap stays in Saddlebunch Keys

Ibis Bay Beach Resort

Southwinds Motel

Parmer's Resort

Hampton Inn Key West FL

Pegasus International Hotel

Alexander Palms Court

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