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

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

1. Hampton Inn Key West FL

Key West

Erika

฿5,664

฿6,372 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.

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

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

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

New Town

Brian

฿4,193

฿5,659 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

3. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

฿3,995

฿5,625 total

includes taxes & fees

27 Oct - 28 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.

4. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿5,828

฿6,556 total

includes taxes & fees

26 Oct - 27 Oct

A swimming pool with lounge chairs and palm trees.

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

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.'

5. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

฿3,905

฿5,336 total

includes taxes & fees

28 Oct - 29 Oct

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

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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.

6. The Perry Hotel & Marina Key West

Stock Island

Jade

฿4,687

฿7,339 total

includes taxes & fees

31 Oct - 1 Nov

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

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

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.

7. Hilton Key West Resort & Marina

Stock Island

Eric A

฿4,095

฿6,567 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 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 hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

8. Margaritaville Beach House Key West

Key West

Richard

฿6,837

฿9,805 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

฿4,193

฿6,602 total

includes taxes & fees

25 Oct - 26 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

฿6,907

฿9,279 total

includes taxes & fees

28 Oct - 29 Oct

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

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

11. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

฿6,636

฿8,974 total

includes taxes & fees

30 Oct - 31 Oct

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

A spacious lobby with a marble floor, leather sofas, and large potted plants.

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

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

12. Beachside Resort & Residences

Key West

Deana

฿3,921

฿7,615 total

includes taxes & fees

27 Oct - 28 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 pool area with blue lounge chairs, a hot tub, and a covered seating area.

13. Ibis Bay Beach Resort

Northside Resort

Andre

฿4,561

฿6,212 total

includes taxes & fees

18 Oct - 19 Oct

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

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, lounge chairs, and umbrellas.

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

14. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿5,094

฿7,654 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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.

15. Sugar Loaf Lodge

Summerland Key

morgan

฿3,988

฿4,487 total

includes taxes & fees

26 Oct - 27 Oct

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

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

16. Havana Cabana at Key West

New Town

Stephanie

฿4,860

฿7,596 total

includes taxes & fees

1 Nov - 2 Nov

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

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

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

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

17. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

฿5,111

฿8,012 total

includes taxes & fees

27 Oct - 28 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 swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.

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.

18. The Laureate Key West

New Town

Eileen

฿5,329

฿6,938 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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

19. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Charlene

฿7,236

฿10,403 total

includes taxes & fees

25 Oct - 26 Oct

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

A sunset view with a thatched structure and a palm tree by a calm body of water.

20. Parmer's Resort

Summerland Key

Mireya

฿4,914

฿6,621 total

includes taxes & fees

3 Nov - 4 Nov

View all properties

Hotels recommended for families in Saddlebunch Keys

Hampton Inn Key West FL

Key West

฿5,664

฿6,372 total

includes taxes & fees

25 Oct - 26 Oct

Sugar Loaf Lodge

Summerland Key

฿3,988

฿4,487 total

includes taxes & fees

26 Oct - 27 Oct

Hilton Key West Resort & Marina

Stock Island

฿4,095

฿6,567 total

includes taxes & fees

27 Oct - 28 Oct

Hilton Garden Inn Key West / The Keys Collection

New Town

฿3,905

฿5,336 total

includes taxes & fees

28 Oct - 29 Oct

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

New Town

฿4,193

฿5,659 total

includes taxes & fees

25 Oct - 26 Oct

The Perry Hotel & Marina Key West

Stock Island

฿4,687

฿7,339 total

includes taxes & fees

31 Oct - 1 Nov

DoubleTree Resort by Hilton Grand Key - Key West

Key West

฿3,995

฿5,625 total

includes taxes & fees

27 Oct - 28 Oct

Courtyard by Marriott Key West Waterfront

Northside Resort

฿5,828

฿6,556 total

includes taxes & fees

26 Oct - 27 Oct

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Top Saddlebunch Keys Hotel Reviews

Havana Cabana at Key West

10/10 Excellent

"The staff was so kind and the vibes were very Key West lol. 10/10"

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."

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."

The Southernmost Inn - Adults Only

10/10 Excellent

"I enjoy staying at this hotel when I am visiting the Keys. Anthony is fabulous at the front desk. It’s close to the action on Duval and a wonderful Italian restaurant called Abbondanza. The pools at the property are always clean and refreshing. A great way to spend the afternoon. This time I was there, they were doing maintenance on the property. You would hear occasional construction noise (sawing, drilling, banging), so it was not as relaxing sitting by the pool. At around 5:00 pm several iguanas came down from the trees to enjoy Happy Hour. The pump on the hot tub was not working, so it was basically a sit bath - with a strong smell of chlorine. It would have been nice to have that working. Other than that, it was a nice stay overall."

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

Southwinds Motel

1321 Simonton Street Key West FL

฿4,659

฿6,372 total

27 Oct - 28 Oct

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,664

฿6,372 total

25 Oct - 26 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)

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! (1,002 reviews)

Alexander Palms Court

715 South St Key West FL

฿7,541

฿8,484 total

19 Oct - 20 Oct

includes taxes & fees

9.4/10 Exceptional! (1,006 reviews)

Find hotels in Saddlebunch Keys, FL from ฿4,487

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. DoubleTree Resort by Hilton Grand Key - Key West

4. Courtyard by Marriott Key West Waterfront

5. Hilton Garden Inn Key West / The Keys Collection

6. The Perry Hotel & Marina Key West

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. Beachside Resort & Residences

13. Ibis Bay Beach Resort

14. Parrot Key Hotel & Villas

15. Sugar Loaf Lodge

16. Havana Cabana at Key West

17. The Reach Key West, Curio Collection by Hilton

18. The Laureate Key West

19. Casa Marina Key West, Curio Collection by Hilton

20. Parmer's Resort

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

Havana Cabana at Key West

The Perry Hotel & Marina Key West

Pier House Resort & Spa

Opal Key Resort & Marina, Key West

Margaritaville Beach House Key West

The Southernmost Inn - Adults Only

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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