The Best Hotels in Cutthroat Harbor Estates, Summerland Key - 2026 Updated Prices

A calm lake with several white birds, including herons and pelicans, on the water's edge.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Cutthroat Harbor Estates hotels

1. Sugar Loaf Lodge

9 km from Cutthroat Harbor Estates

Marjorie

฿4,426 total

includes taxes & fees

16 Aug - 17 Aug

2. Atlantic View Luxury Villa with Pool

2.5 km from Cutthroat Harbor Estates

Preetam

฿37,287 total

includes taxes & fees

11 Aug - 12 Aug

3. Looe Key Reef Resort

7.2 km from Cutthroat Harbor Estates

Christopher

฿3,752 total

includes taxes & fees

1 Sept - 2 Sept

4. Parmer's Resort

9.2 km from Cutthroat Harbor Estates

John

฿4,841 total

includes taxes & fees

17 Aug - 18 Aug

5. Starlight Serenity - Hideaway w Stunning Views

6.1 km from Cutthroat Harbor Estates

max

฿21,974 total

includes taxes & fees

17 Aug - 18 Aug

1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

6. Old Wooden Bridge Resort and Marina

13.8 km from Cutthroat Harbor Estates

Kathy

฿7,996 total

includes taxes & fees

1 Sept - 2 Sept

7. Hyatt Vacation Club at Windward Pointe, Key West

30 km from Cutthroat Harbor Estates

Adam

฿8,424 total

includes taxes & fees

2 Sept - 3 Sept

8. Hilton Key West Resort & Marina

27.5 km from Cutthroat Harbor Estates

Alondra

฿6,524 total

includes taxes & fees

16 Aug - 17 Aug

Outdoor pool, pool umbrellas, pool loungers

9. Hampton Inn Key West FL

29.8 km from Cutthroat Harbor Estates

Marines

฿5,501 total

includes taxes & fees

30 Aug - 31 Aug

Suite, 1 Bedroom, Ocean View (Spacious | King) | In-room safe, desk, blackout curtains, soundproofing

10. The Laureate Key West

30.1 km from Cutthroat Harbor Estates

Robert

฿6,844 total

includes taxes & fees

9 Aug - 10 Aug

Outdoor pool, open 7:00 AM to 9:00 PM, pool cabanas (surcharge)

11. DoubleTree Resort by Hilton Grand Key - Key West

29.6 km from Cutthroat Harbor Estates

Chandra

฿5,549 total

includes taxes & fees

16 Aug - 17 Aug

12. The Perry Hotel & Marina Key West

28.4 km from Cutthroat Harbor Estates

Mauricio

฿6,969 total

includes taxes & fees

10 Aug - 11 Aug

13. Hyatt Vacation Club at Beach House, Key West

29.2 km from Cutthroat Harbor Estates

Lakshit

฿9,709 total

includes taxes & fees

30 Aug - 31 Aug

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

29.5 km from Cutthroat Harbor Estates

Fernando

฿5,579 total

includes taxes & fees

19 Aug - 20 Aug

15. The Fairhaven House at Solaire Lunara Bay

26.9 km from Cutthroat Harbor Estates

฿104,420 total

includes taxes & fees

8 Sept - 9 Sept

Outdoor pool, open 6:00 AM to 10:00 PM, pool cabanas (surcharge)

16. Hilton Garden Inn Key West / The Keys Collection

29.5 km from Cutthroat Harbor Estates

Oscar

฿4,702 total

includes taxes & fees

20 Aug - 21 Aug

Ocean View 3BR Condo with Rooftop Balcony | Balcony

17. Beachside Resort & Residences

29.4 km from Cutthroat Harbor Estates

Nicole

฿7,129 total

includes taxes & fees

9 Aug - 10 Aug

2 outdoor pools, open 7:00 AM to 10:00 PM, pool cabanas (surcharge)

18. Blue Flamingo Resort Key West

29.6 km from Cutthroat Harbor Estates

Robert

฿6,349 total

includes taxes & fees

7 Sept - 8 Sept

19. Aqua Lodges at Hurricane Hole Marina

28.8 km from Cutthroat Harbor Estates

Emily

฿9,191 total

includes taxes & fees

13 Aug - 14 Aug

Condo | Living area | 32-inch Smart TV with satellite channels

20. Coconut Mallory Marina and Resort Condo

29.4 km from Cutthroat Harbor Estates

Paris

฿43,400 total

includes taxes & fees

9 Aug - 10 Aug

View all properties

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas for the activities you enjoy most.

A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

See properties

Boat traveling under the Seven Mile Bridge, Florida Keys, USA

Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Florida Keys Beaches.

See properties

Aerial view of scenic coastal road with turquoise water and bridge, Summerland Key, Florida, United States.

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

See properties

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Big Pine Key Flea Market and Venture Out Keys.

See properties

Top Cutthroat Harbor Estates Hotel Reviews

The Perry Hotel & Marina Key West

8/10 Good

"Room was small but nice and very clean. Biggest let down was that we chartered a boat and stayed at this hotel due to the marina and their restaurant cooking our catch for us. We took our catch to the restaurant when we returned, only to be told the restaurant was bought out for the night. No notice, no apology. Received a text hours later telling everyone it would be closed to hotel patrons that night."

Blue Flamingo Resort Key West

8/10 Good

"The hotel was ok, nothing special to need to pay $50 a day resort fee. The rooms are your typical hotel room, nothing fancy. One hard chair to sit on, no couch or other seating besides bed. No clock or microwave in room. Bathroom has a standing glass shower with no privacy which is not convenient when someone has to use toilet/ bathroom. The backyard was pretty nice with 2 pools, games, small workout room and plenty of seating. Did not see a hot tub on property which is what is advertised on Expedia website. We had a Ocean view room on 5th floor which faces the main road / busy highway. Circle k and mcdonalds very close to walk to, can see from hotel.Food at the property is extremely expensive. Went down to the toasted coconut for breakfast one morning, ordered 2 parfait which are $14 each, 1 breakfast meal which was $20, 2 small orange juice at $5 a juice. They automatically add on a 18% gratuity to the check and breakfast for 3 was $77 and some change, needless to say that was our only time getting breakfast there. Go next door for breakfast at mcdonalds and save a ton of money. The shuttle is very convenient as you are far away from the action, just schedule ahead of time at front desk."

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"The property is absolutely STUNNING. Balconies with rocking chairs, table and telescope. Gas grills, lovely infinity pool and hot tub. Close to the airport, over 4 days I heard the planes like 5 or 6 times and that was it. Need to Uber or Cab down to Old Town. Maria was AWESOME, she showed us to our room. Room was extremely clean and beautiful, had everything we needed. It was not ready when we arrived but they secured all.of our luggage so we could go ahead and explore and use the amenities, then delivered the luggage to our room for us!! We had so much fun, delicious drinks at the bar, the Benihana out front is great too!! We will DEFINITELY come back to this property again and again. Also great for handicap access, one of our party is disabled and she had zero problems with the stay. Would give more"

Aqua Lodges at Hurricane Hole Marina

8/10 Good

"Loved our stay at Aqua Lodge during the last week of July 2026. Rooms were larger than anticipated, bathroom and shower full size and better than I thought (if you're a boater, you know what I mean). Location is fantastic. Only area Aqua Lodge could improve on is with regard to linens. Towels are extremely cheap, course, and very threadbare. Bed sheets and pillow cases are similar. Having said that, the units are professionally crafted floating hotel rooms mounted on pontoons. You have the option of tying your boat up alongside and having quick access to it. Truly enjoyed our stay at Aqua Lodge in Hurricane Hole Marina on Stock Island and will probably be back in the not too distant future."

Sugarloaf Key Hotel at KOA Resort

8/10 Good

"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina rental closes super early and last call for rental is too early as well but the place is nice especially if you have children. It’s clean, easy to move around, close to Key West. Bartenders are all super nice and there are different activities like smores or live singers. It was a great experience. We will be back."

Frequently asked questions

What's it like in Cutthroat Harbor Estates?

Travellers to Summerland Key's Cutthroat Harbor Estates neighbourhood will be sure to enjoy a stay here.

How many hotels are there in Cutthroat Harbor Estates?

Expedia has 68 hotels and other accommodation options in Cutthroat Harbor Estates to choose from, making this an ideal home base for exploring the greater Summerland Key area.

If I need to cancel my hotel reservation in Cutthroat Harbor Estates, will I receive a refund?

Yes! Most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and receive a refund within 24 hours of booking. Add dates, click "Search", then use the filter option "fully refundable" to get the best options available in Cutthroat Harbor Estates.

What are the top things to see and do in Cutthroat Harbor Estates?

A few places to visit in the area around Cutthroat Harbor Estates include Venture Key, Out Key and Venture Out Keys. Crab Key and Pye Key are also worth a visit when you're out sightseeing in Summerland Key.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Cutthroat Harbor Estates on Expedia.com

Search Hotels in Cutthroat Harbor Estates, Summerland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cutthroat Harbor Estates hotels

1. Sugar Loaf Lodge

2. Atlantic View Luxury Villa with Pool

3. Looe Key Reef Resort

4. Parmer's Resort

5. Starlight Serenity - Hideaway w Stunning Views

6. Old Wooden Bridge Resort and Marina

7. Hyatt Vacation Club at Windward Pointe, Key West

8. Hilton Key West Resort & Marina

9. Hampton Inn Key West FL

10. The Laureate Key West

11. DoubleTree Resort by Hilton Grand Key - Key West

12. The Perry Hotel & Marina Key West

13. Hyatt Vacation Club at Beach House, Key West

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

15. The Fairhaven House at Solaire Lunara Bay

16. Hilton Garden Inn Key West / The Keys Collection

17. Beachside Resort & Residences

18. Blue Flamingo Resort Key West

19. Aqua Lodges at Hurricane Hole Marina

20. Coconut Mallory Marina and Resort Condo

Where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Cudjoe Gardens

Bay Point

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

The Perry Hotel & Marina Key West

Frequently asked questions

Explore a world of travel with Expedia