Top Cutthroat Harbor Estates Hotels from ￥11,175

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Our top choices for Cutthroat Harbor Estates hotels

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

1. Sugar Loaf Lodge

9 km from Cutthroat Harbor Estates

David

￥17,808 total

includes taxes & fees

Nov 30 - Dec 1

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

2. Parmer's Resort

9.2 km from Cutthroat Harbor Estates

Natalie

￥32,755 total

includes taxes & fees

Dec 1 - Dec 2

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

3. Looe Key Reef Resort

7.2 km from Cutthroat Harbor Estates

Stephen

￥31,062 total

includes taxes & fees

Nov 16 - Nov 17

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

4. The Perry Hotel & Marina Key West

28.4 km from Cutthroat Harbor Estates

Dharmesh Raju

￥29,663 total

includes taxes & fees

Nov 30 - Dec 1

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

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

29.5 km from Cutthroat Harbor Estates

Sandra

￥28,617 total

includes taxes & fees

Nov 29 - Nov 30

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

6. Hampton Inn Key West FL

29.8 km from Cutthroat Harbor Estates

John

￥27,701 total

includes taxes & fees

Nov 17 - Nov 18

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

7. Old Wooden Bridge Resort and Marina

13.8 km from Cutthroat Harbor Estates

Anthony

￥35,055 total

includes taxes & fees

Dec 4 - Dec 5

A hotel with a swimming pool, sun loungers, and palm trees.

8. Blue Flamingo Resort Key West

29.6 km from Cutthroat Harbor Estates

Sigrid A

￥29,877 total

includes taxes & fees

Nov 15 - Nov 16

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

9. Hyatt Vacation Club at Windward Pointe, Key West

30 km from Cutthroat Harbor Estates

John

￥35,500 total

includes taxes & fees

Nov 30 - Dec 1

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

10. Hilton Key West Resort & Marina

27.5 km from Cutthroat Harbor Estates

Kevin

￥33,703 total

includes taxes & fees

Nov 16 - Nov 17

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

11. Atlantic View Luxury Villa with Pool

2.5 km from Cutthroat Harbor Estates

Preetam

￥156,043 total

includes taxes & fees

Nov 15 - Nov 16

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

12. Hyatt Vacation Club at Beach House, Key West

29.2 km from Cutthroat Harbor Estates

Joshua

￥40,521 total

includes taxes & fees

Nov 17 - Nov 18

A swimming pool with lounge chairs and palm trees.

13. Hilton Garden Inn Key West / The Keys Collection

29.5 km from Cutthroat Harbor Estates

Darlene

￥26,363 total

includes taxes & fees

Nov 17 - Nov 18

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

14. Havana Cabana at Key West

30.3 km from Cutthroat Harbor Estates

Robert

￥31,454 total

includes taxes & fees

Nov 29 - Nov 30

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

15. The Laureate Key West

30.1 km from Cutthroat Harbor Estates

Eileen

￥33,062 total

includes taxes & fees

Nov 30 - Dec 1

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

16. Aqua Lodges at Hurricane Hole Marina

28.8 km from Cutthroat Harbor Estates

Kagni

￥52,254 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a hanging hammock and a view of a green landscape.

17. Starlight Serenity - Hideaway w Stunning Views

6.1 km from Cutthroat Harbor Estates

max

￥112,220 total

includes taxes & fees

Nov 19 - Nov 20

A beachside resort with a wooden deck, palm trees, and a sunset view.

18. Grand Marina Suite by Brightwild Waterfront

27 km from Cutthroat Harbor Estates

Pawel

￥108,928 total

includes taxes & fees

Nov 20 - Nov 21

A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

19. The Grenada Suite Pool View Private Balcony

29.8 km from Cutthroat Harbor Estates

Luis

￥88,607 total

includes taxes & fees

Nov 30 - Dec 1

View all properties

Compare popular hotels in Cutthroat Harbor Estates

Property	Star rating	Guest rating
Parmer's Resort	2.5 star property	9.0 Wonderful 1,001 reviews	View
The Perry Hotel & Marina Key West	4.0 star property	9.4 Exceptional 1,318 reviews	View
Hyatt Vacation Club at Beach House, Key West	3.5 star property	9.4 Exceptional 1,290 reviews	View
Fairfield by Marriott Inn & Suites Key West at The Keys Collection	3.5 star property	8.8 Excellent 1,204 reviews	View
Hampton Inn Key West FL	2.5 star property	9.0 Wonderful 1,582 reviews	View

Hotels recommended for families in Cutthroat Harbor Estates

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

￥84,582 total

includes taxes & fees

Nov 29 - Nov 30

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.

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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.

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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.

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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.

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Top Cutthroat Harbor Estates Hotel Reviews

Parmer's Resort

Summerland Key

10/10 Excellent

Michael

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Lindsay

Havana Cabana at Key West

New Town

10/10 Excellent

Eliana

Hampton Inn Key West FL

Key West

10/10 Excellent

Karen

Hyatt Vacation Club at Beach House, Key West

Key West

10/10 Excellent

Sonia

Sugar Loaf Lodge

Summerland Key

10/10 Excellent

Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...

Momi

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

DoubleTree Resort by Hilton Grand Key - Key West

Key West

10/10 Excellent

Hector

Old Wooden Bridge Resort and Marina

Punta Brisa

10/10 Excellent

Our stay in cabin 9 (turquoise one) was great. This cabin was perfect for our needs and we brought two dogs with us, no issues with that. We loved our stay but to be transparent this is really no frills. There is no sink sponge, no aluminum foil no nothing extra in the kitchen so bring your own!! The mattresses are VERY firm. There were a few small cosmetic issues that could be addressed in this cabin that would make a huge difference, example, crooked drawer front in kitchen, pinned drapes...

Nancy

The Laureate Key West

New Town

10/10 Excellent

We stayed two nights in the 3-bedroom suite. Everything, from the moment of arrival, was top rate. The front desk attendant was in contact with me via text to ensure a smooth and efficient check in before arrival and was a great help with local recommendations at check in. Departure took 30 seconds yet the desk attendant took the time to ask how everything was, if I needed anything, wished me well, etc. The suite was beautiful appointed and the furniture very functional and comfortable. Our...

Shannon

Aqua Lodges at Hurricane Hole Marina

Stock Island

10/10 Excellent

Abigail

Hilton Garden Inn Key West / The Keys Collection

New Town

10/10 Excellent

Charity

Grand Marina Suite by Brightwild Waterfront

Stock Island

10/10 Excellent

Pawel

Starlight Serenity - Hideaway w Stunning Views

Summerland Key

10/10 Excellent

max

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.

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Find hotels in Cutthroat Harbor Estates, Summerland Key from ￥11,175

Change your mind

Treat yourself

Be picky

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Our top choices for Cutthroat Harbor Estates hotels

1. Sugar Loaf Lodge

2. Parmer's Resort

3. Looe Key Reef Resort

4. The Perry Hotel & Marina Key West

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

6. Hampton Inn Key West FL

7. Old Wooden Bridge Resort and Marina

8. Blue Flamingo Resort Key West

9. Hyatt Vacation Club at Windward Pointe, Key West

10. Hilton Key West Resort & Marina

11. Atlantic View Luxury Villa with Pool

12. Hyatt Vacation Club at Beach House, Key West

13. Hilton Garden Inn Key West / The Keys Collection

14. Havana Cabana at Key West

15. The Laureate Key West

16. Aqua Lodges at Hurricane Hole Marina

17. Starlight Serenity - Hideaway w Stunning Views

18. Grand Marina Suite by Brightwild Waterfront

19. The Grenada Suite Pool View Private Balcony

Compare popular hotels in Cutthroat Harbor Estates

Hotels recommended for families in Cutthroat Harbor Estates

SAVE BIG $$$ NOV./DEC. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Cudjoe Gardens

Bay Point

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

Parmer's Resort

10/10 Excellent

Frequently Asked Questions

What's it like in Cutthroat Harbor Estates?

What's the best accommodation in Cutthroat Harbor Estates?

How many hotels will I find in Cutthroat Harbor Estates?

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

Where can I learn more about changing or cancelling my trip to Cutthroat Harbor Estates?

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

Explore a world of travel with Expedia