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

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

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

1. Hampton Inn Key West FL

Key West

Erika

Rp3.031.522

Rp3.410.463 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 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.

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

2. The Perry Hotel & Marina Key West

Stock Island

Jade

Rp2.508.421

Rp3.927.852 total

includes taxes & fees

31 Oct - 1 Nov

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

A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.

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

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

3. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

Rp2.134.038

Rp3.005.018 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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

4. Hilton Key West Resort & Marina

Stock Island

Eric A

Rp2.191.665

Rp3.514.997 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

New Town

Brian

Rp2.244.044

Rp3.028.967 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

6. Margaritaville Beach House Key West

Key West

Richard

Rp3.491.085

Rp5.054.352 total

includes taxes & fees

29 Oct - 30 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 modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

7. Blue Flamingo Resort Key West

New Town

Esteban

Rp2.239.665

Rp3.526.667 total

includes taxes & fees

27 Oct - 28 Oct

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

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

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

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

8. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

Rp3.680.878

Rp4.948.197 total

includes taxes & fees

28 Oct - 29 Oct

A swimming pool with lounge chairs and palm trees.

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

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

9. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

Rp1.901.069

Rp2.643.298 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A beach with palm trees, lounge chairs, and umbrellas.

10. Parrot Key Hotel & Villas

Northside Resort

Anthony

Rp2.721.256

Rp4.088.687 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

A modern restaurant with a wooden counter, seating area, and large windows.

11. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

Rp3.112.974

Rp3.502.095 total

includes taxes & fees

28 Oct - 29 Oct

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

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

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

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

12. Havana Cabana at Key West

New Town

Stephanie

Rp2.601.010

Rp4.065.379 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 spacious living area with a large window, a dining table, and comfortable seating.

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

A two-story building with a balcony, arched windows, and a green roof.

13. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

Rp4.003.762

Rp5.311.442 total

includes taxes & fees

19 Oct - 20 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 spacious lobby with a marble floor, leather sofas, and large potted plants.

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

14. Beachside Resort & Residences

Key West

Brenna

Rp2.094.260

Rp4.068.015 total

includes taxes & fees

27 Oct - 28 Oct

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 set for guests, overlooking a calm sea and a pier.

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

15. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

Rp2.729.267

Rp4.281.241 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 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.

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.

16. The Laureate Key West

New Town

Eileen

Rp2.846.577

Rp3.706.100 total

includes taxes & fees

29 Oct - 30 Oct

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

A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

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.

17. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Charlene

Rp3.865.258

Rp5.556.868 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

18. Hyatt Centric Key West Resort and Spa

Key West Historic District

Jennifer

Rp4.278.817

Rp6.062.403 total

includes taxes & fees

29 Oct - 30 Oct

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

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

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

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

19. Sugar Loaf Lodge

Summerland Key

morgan

Rp2.130.457

Rp2.396.854 total

includes taxes & fees

18 Oct - 19 Oct

A pool area with lounge chairs and a cabana.

A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

A waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

A balcony with a table set for breakfast, overlooking the sea.

20. Ocean Key Resort - A Noble House Resort

Key West Historic District

Patrick

Rp5.006.574

Rp7.082.539 total

includes taxes & fees

29 Oct - 30 Oct

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Top Saddlebunch Keys Hotel Reviews

The Perry Hotel & Marina Key West

10/10 Excellent

"This is a great place just minutes away from Key West proper. The rooms are nice (at least, ours was), the staff was very pleasant and helpful, and the property is well-maintained. Parking is in a gravel lot adjacent to the buildings and very close to the lobby, elevators, and restaurants. We did not use any of their resort amenities, so I will not opine on their quality. I will note that you need to add the daily resort fee to your room charge and tax to estimate the daily rate for staying there."

Pier House Resort & Spa

10/10 Excellent

"The perfect place to stay! Quiet, great soft music at the outside bar that we could hear on the private beach. Close to everything. Helpful staff. Only thing is it’s very expensive."

Havana Cabana at Key West

10/10 Excellent

"Great property, very clean and great friendly staff. Pool and bar was awesome."

Opal Key Resort & Marina, Key West

10/10 Excellent

"The hotel location, cleanliness and view are awesome. No complaints about anything. The unlimited cold water bottles were icing on the cake. If I’m so happy with a partial sea view room, I’ll be even happier with an oceanfront room. Maybe next time."

Margaritaville Beach House Key West

10/10 Excellent

"Very nice and friendly staff. It was a great place."

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"The resort staff was welcoming upon our arrival and the check-in process was efficient. Throughout our stay the members of your concierge service were extremely helpful, even proactively looking for and directing us to a beach that was clear of sargassum. The shuttle service was amazing with a great schedule."

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."

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."

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"Great property"

More cheap stays in Saddlebunch Keys

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Rp2.441.004

Rp3.324.809 total

18 Oct - 19 Oct

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

Rp2.488.517

Rp3.403.808 total

26 Oct - 27 Oct

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

Rp3.031.522

Rp3.410.463 total

25 Oct - 26 Oct

includes taxes & fees

Parmer's Resort

565 Barry Avenue Summerland Key FL

Rp2.629.889

Rp3.543.942 total

3 Nov - 4 Nov

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

Rp3.228.840

Rp4.540.557 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

Rp4.036.050

Rp4.540.646 total

19 Oct - 20 Oct

includes taxes & fees

9.4/10 Exceptional! (1,006 reviews)

Find hotels in Saddlebunch Keys, FL from Rp2.396.854

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Saddlebunch Keys

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Saddlebunch Keys hotels

1. Hampton Inn Key West FL

2. The Perry Hotel & Marina Key West

3. DoubleTree Resort by Hilton Grand Key - Key West

4. Hilton Key West Resort & Marina

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

6. Margaritaville Beach House Key West

7. Blue Flamingo Resort Key West

8. Hyatt Vacation Club at Windward Pointe, Key West

9. Hilton Garden Inn Key West / The Keys Collection

10. Parrot Key Hotel & Villas

11. Courtyard by Marriott Key West Waterfront

12. Havana Cabana at Key West

13. Hyatt Vacation Club at Beach House, Key West

14. Beachside Resort & Residences

15. The Reach Key West, Curio Collection by Hilton

16. The Laureate Key West

17. Casa Marina Key West, Curio Collection by Hilton

18. Hyatt Centric Key West Resort and Spa

19. Sugar Loaf Lodge

20. Ocean Key Resort - A Noble House Resort

Top Saddlebunch Keys Hotel Reviews

The Perry Hotel & Marina Key West

Pier House Resort & Spa

Havana Cabana at Key West

Opal Key Resort & Marina, Key West

Margaritaville Beach House Key West

DoubleTree Resort by Hilton Grand Key - Key West

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

Beachside Resort & Residences

Casa Marina Key West, Curio Collection by Hilton

More cheap stays in Saddlebunch Keys

Ibis Bay Beach Resort

Southwinds Motel

Hampton Inn Key West FL

Parmer's Resort

Pegasus International Hotel

Alexander Palms Court

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