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

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Check prices for these dates

This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

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Our top choices for Cutthroat Harbor Estates hotels

Karaoke room

1. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
7.2 km from Cutthroat Harbor Estates
7.6 out of 10, Good, (1,003 reviews)
"Had a great time over the weekend . Great vibe!"
United States
Michel
The price is AED 278
AED 313 total
includes taxes & fees
27 Sep - 28 Sep
Looe Key Reef Resort
Exterior

2. Parmer's Resort

Parmer's Resort
2.5 star property
9.2 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,003 reviews)
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
United States
Mireya
The price is AED 528
AED 713 total
includes taxes & fees
4 Oct - 5 Oct
Parmer's Resort
1 Bedroom Aqualodge # 6 Tarpon | Living area | Flat-screen TV

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
13.8 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (372 reviews)
"Nice place"
United States
abhimanyu
The price is AED 331
AED 888 total
includes taxes & fees
27 Sep - 28 Sep
Old Wooden Bridge Resort and Marina
Exterior

4. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
9 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,000 reviews)
"I didn't stay in much, mostly sleeping at night and spending the rest of my time in Key West. That said, this place is a great way to mix in quiet stays away while being well situated to head into Key West (approximately 15 minutes away sans traffic). I'd stay here again without hesitation and you should really consider booking here!"
United States
Kevin
The price is AED 364
AED 409 total
includes taxes & fees
27 Sep - 28 Sep
Sugar Loaf Lodge
Exterior

5. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
2.5 km from Cutthroat Harbor Estates
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is AED 1,901
AED 3,585 total
includes taxes & fees
25 Sep - 26 Sep
Atlantic View Luxury Villa with Pool
House | Terrace/patio

6. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
6.1 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is AED 838
AED 2,283 total
includes taxes & fees
30 Sep - 1 Oct
Starlight Serenity - Hideaway w Stunning Views
Exterior

7. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
4.0 star property
27.5 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,811 reviews)
"Beautiful property would stay there again"
United States
Molly
The price is AED 419
AED 691 total
includes taxes & fees
30 Sep - 1 Oct
Hilton Key West Resort & Marina
Marina

8. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
28.4 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,317 reviews)
"Beautiful place to stay, would definitely stay here again."
United States
Jade
The price is AED 457
AED 739 total
includes taxes & fees
29 Sep - 30 Sep
The Perry Hotel & Marina Key West
Outdoor pool, pool umbrellas, sun loungers

9. Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
29.8 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,520 reviews)
"Very clean comfortable bed , very friendly staff Very clean pool 💕"
United States
Rabia
The price is AED 496
AED 558 total
includes taxes & fees
29 Sep - 30 Sep
Hampton Inn Key West FL
Property grounds

10. Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
3.5 star property
29.2 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,245 reviews)
"Great place to stay with the family"
United States
Rachel
The price is AED 637
AED 882 total
includes taxes & fees
7 Oct - 8 Oct
Hyatt Vacation Club at Beach House, Key West
Outdoor pool, open 7:00 AM to 9:00 PM, cabanas (surcharge), sun loungers

11. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
29.6 km from Cutthroat Harbor Estates
8.4 out of 10, Very good, (1,106 reviews)
"The hotel was clean, great customer service, and the food was really good!"
United States
Craige
The price is AED 379
AED 550 total
includes taxes & fees
30 Sep - 1 Oct
DoubleTree Resort by Hilton Grand Key - Key West
Ocean View 3BR Condo with Rooftop Balcony | Balcony

12. Beachside Resort & Residences

Beachside Resort & Residences
3.5 star property
29.4 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,549 reviews)
"Great location"
United States
James
The price is AED 321
AED 712 total
includes taxes & fees
27 Sep - 28 Sep
Beachside Resort & Residences
Property grounds

13. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
30 km from Cutthroat Harbor Estates
9.4 out of 10, Exceptional, (1,290 reviews)
"Amazing spa, beautiful property, friendly staff and gorgeous beaches."
United States
Tina
The price is AED 682
AED 933 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Vacation Club at Windward Pointe, Key West
Outdoor pool

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

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
3.5 star property
29.5 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (1,133 reviews)
"Nice place"
United States
Travis
The price is AED 426
AED 583 total
includes taxes & fees
30 Sep - 1 Oct
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
2 outdoor pools, open 7:00 AM to 10:00 PM, cabanas (surcharge)

15. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
29.6 km from Cutthroat Harbor Estates
8.6 out of 10, Excellent, (2,681 reviews)
"Great spot will stay again"
United States
Esteban
The price is AED 434
AED 695 total
includes taxes & fees
27 Sep - 28 Sep
Blue Flamingo Resort Key West
House | 2 bedrooms, soundproofing

16. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
27 km from Cutthroat Harbor Estates
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
The price is AED 1,152
AED 2,189 total
includes taxes & fees
26 Sep - 27 Sep
Grand Marina Suite by Brightwild Waterfront
Outdoor pool, open 6:00 AM to 10:00 PM, cabanas (surcharge)

17. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
3.5 star property
29.5 km from Cutthroat Harbor Estates
8.2 out of 10, Very good, (1,328 reviews)
"Love the breakfast and pool/ bar area"
United States
Walt
The price is AED 388
AED 540 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Key West / The Keys Collection
Outdoor pool, sun loungers

18. Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
30.3 km from Cutthroat Harbor Estates
9.0 out of 10, Wonderful, (1,852 reviews)
"Absolutely going to be staying here again. Our family throughly enjoyed the hotel, amenities and location to Key West"
United States
Silvia
The price is AED 408
AED 691 total
includes taxes & fees
27 Sep - 28 Sep
Havana Cabana at Key West
Suite, 1 Bedroom, Ocean View (Spacious | King) | In-room safe, desk, blackout drapes, soundproofing

19. The Laureate Key West

The Laureate Key West
3.5 star property
30.1 km from Cutthroat Harbor Estates
9.2 out of 10, Wonderful, (1,019 reviews)
"We loved the room and location!"
United States
Mailyn
The price is AED 584
AED 760 total
includes taxes & fees
27 Sep - 28 Sep
The Laureate Key West
Front of property

20. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
28.8 km from Cutthroat Harbor Estates
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is AED 361
AED 1,034 total
includes taxes & fees
26 Sep - 27 Sep
Aqua Lodges at Hurricane Hole Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most.
A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

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 Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.

Top Cutthroat Harbor Estates Hotel Reviews

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Very quiet and clean. Staff were excellent. Well appointed accommodation."
Norma 2-night trip
Posted 5 hours ago
Beachside Resort & Residences

Frequently asked questions

What's it like in Cutthroat Harbor Estates?
Travelers to Summerland Key's Cutthroat Harbor Estates neighborhood will be sure to enjoy a stay in this neighborhood.
What's the best accommodation in Cutthroat Harbor Estates?
For your stay in Cutthroat Harbor Estates, Just 20 miles from Key West! Oceanfront, dockage, swimming pool is one of the top choices based on our traveler data.
How many hotels will I find in Cutthroat Harbor Estates?
Expedia has 69 hotels and other accommodations 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 reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Add dates, click "Search", then you can filter by "fully refundable" to view the best deals in Cutthroat Harbor Estates.
Where can I learn more about changing or cancelling my trip to Cutthroat Harbor Estates?
For more details about changing or cancelling your trip to Cutthroat Harbor Estates, click here.
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.