Saddlebunch Keys Holiday Rentals, Florida: Private House Rentals

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Go beyond your typical stay in Saddlebunch Keys

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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 balcony, a bed, a desk, and two chairs.

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

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

1. Hampton Inn Key West FL

Key West

Erika

฿5,649

฿6,355 total

includes taxes & fees

25 Oct - 26 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 modern office space with a reception desk, computer, and seating area.

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

New Town

Brian

฿4,181

฿5,644 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 hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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

3. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,717

฿6,220 total

includes taxes & fees

16 Nov - 17 Nov

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

4. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

฿3,984

฿5,610 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

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

5. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿5,812

฿6,538 total

includes taxes & fees

26 Oct - 27 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 bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

6. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

฿3,546

฿4,929 total

includes taxes & fees

28 Oct - 29 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 clear view of turquoise ocean water and a blue sky with clouds.

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

7. Hilton Key West Resort & Marina

Stock Island

Eric A

฿4,087

฿6,553 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 beach with a palm tree and two chairs.

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

8. Margaritaville Beach House Key West

Key West

Siamak

฿6,837

฿9,805 total

includes taxes & fees

30 Oct - 31 Oct

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

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

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

9. Blue Flamingo Resort Key West

New Town

Esteban

฿4,181

฿6,585 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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.

10. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

฿6,214

฿8,499 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

11. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

฿6,377

฿8,679 total

includes taxes & fees

31 Oct - 1 Nov

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 pool area with blue lounge chairs, a hot tub, and a covered seating area.

12. Ibis Bay Beach Resort

Northside Resort

Andre

฿4,561

฿6,212 total

includes taxes & fees

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

13. Beachside Resort & Residences

Key West

Deana

฿3,910

฿7,595 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

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

14. Havana Cabana at Key West

New Town

Stephanie

฿4,813

฿7,537 total

includes taxes & fees

2 Nov - 3 Nov

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.

15. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿5,094

฿7,654 total

includes taxes & fees

29 Oct - 30 Oct

A resort with a pool, palm trees, and a thatched-roof structure.

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

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

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

16. Sugar Loaf Lodge

Summerland Key

morgan

฿3,977

฿4,475 total

includes taxes & fees

8 Nov - 9 Nov

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 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 marina with jet skis docked in front of a hotel with a dock and a boat in the background.

17. Hyatt Centric Key West Resort and Spa

Key West Historic District

Joseph

฿8,456

฿11,845 total

includes taxes & fees

2 Nov - 3 Nov

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

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

18. The Laureate Key West

New Town

Eileen

฿5,314

฿6,919 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

19. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

฿5,099

฿7,999 total

includes taxes & fees

26 Oct - 27 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 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.

20. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Charlene

฿7,216

฿10,374 total

includes taxes & fees

25 Oct - 26 Oct

View all properties

Hotels recommended for families in Saddlebunch Keys

Hampton Inn Key West FL

Key West

฿5,649

฿6,355 total

includes taxes & fees

25 Oct - 26 Oct

Sugar Loaf Lodge

Summerland Key

฿3,977

฿4,475 total

includes taxes & fees

15 Nov - 16 Nov

Hilton Key West Resort & Marina

Stock Island

฿4,087

฿6,553 total

includes taxes & fees

25 Oct - 26 Oct

Hilton Garden Inn Key West / The Keys Collection

New Town

฿3,546

฿4,929 total

includes taxes & fees

28 Oct - 29 Oct

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

New Town

฿4,181

฿5,644 total

includes taxes & fees

25 Oct - 26 Oct

The Perry Hotel & Marina Key West

Stock Island

฿3,717

฿6,220 total

includes taxes & fees

16 Nov - 17 Nov

DoubleTree Resort by Hilton Grand Key - Key West

Key West

฿3,984

฿5,610 total

includes taxes & fees

28 Oct - 29 Oct

Courtyard by Marriott Key West Waterfront

Northside Resort

฿5,812

฿6,538 total

includes taxes & fees

26 Oct - 27 Oct

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Top Saddlebunch Keys Hotel Reviews

Southernmost Beach Resort and Guesthouses

8/10 Good

"👍"

Havana Cabana at Key West

10/10 Excellent

"So Pretty and clean the place"

Pier House Resort & Spa

10/10 Excellent

"This resort has everything with the best hospitality! I highly recommend this resort for anyone that wants to enjoy Key West with total relaxation! 😎"

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."

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."

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

฿4,561

฿6,212 total

18 Oct - 19 Oct

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,649

฿6,355 total

25 Oct - 26 Oct

includes taxes & fees

Southwinds Motel

1321 Simonton Street Key West FL

฿4,659

฿6,372 total

26 Oct - 27 Oct

includes taxes & fees

Parmer's Resort

565 Barry Avenue Summerland Key FL

฿4,914

฿6,621 total

3 Nov - 4 Nov

includes taxes & fees

9/10 Wonderful! (1,001 reviews)

Alexander Palms Court

715 South St Key West FL

฿7,520

฿8,461 total

19 Oct - 20 Oct

includes taxes & fees

9.4/10 Exceptional! (1,000 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

฿6,033

฿8,483 total

1 Nov - 2 Nov

includes taxes & fees

8.2/10 Very good! (1,000 reviews)

Find hotels in Saddlebunch Keys, FL from ฿4,475

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

3. The Perry Hotel & Marina Key West

4. DoubleTree Resort by Hilton Grand Key - Key West

5. Courtyard by Marriott Key West Waterfront

6. Hilton Garden Inn Key West / The Keys Collection

7. Hilton Key West Resort & Marina

8. Margaritaville Beach House Key West

9. Blue Flamingo Resort Key West

10. Hyatt Vacation Club at Windward Pointe, Key West

11. Hyatt Vacation Club at Beach House, Key West

12. Ibis Bay Beach Resort

13. Beachside Resort & Residences

14. Havana Cabana at Key West

15. Parrot Key Hotel & Villas

16. Sugar Loaf Lodge

17. Hyatt Centric Key West Resort and Spa

18. The Laureate Key West

19. The Reach Key West, Curio Collection by Hilton

20. Casa Marina Key West, Curio Collection by Hilton

Hotels recommended for families in Saddlebunch Keys

Hampton Inn Key West FL

Sugar Loaf Lodge

Hilton Key West Resort & Marina

Hilton Garden Inn Key West / The Keys Collection

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

The Perry Hotel & Marina Key West

DoubleTree Resort by Hilton Grand Key - Key West

Courtyard by Marriott Key West Waterfront

Top Saddlebunch Keys Hotel Reviews

Southernmost Beach Resort and Guesthouses

Havana Cabana at Key West

Pier House Resort & Spa

The Perry Hotel & Marina Key West

Opal Key Resort & Marina, Key West

Margaritaville Beach House 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

Hampton Inn Key West FL

Southwinds Motel

Parmer's Resort

Alexander Palms Court

Pegasus International Hotel

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