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.

What's a favourite hotel to stay 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 traveller data.

How many hotels are there in Cutthroat Harbor Estates?

Expedia has 74 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.

Cutthroat Harbor Estates Hotels: 1,355 Cheap Accommodation in Cutthroat Harbor Estates

1355 Cheap Hotels in Cutthroat Harbor Estates - Specials, Reviews, & Last Minute Deals

"Perfect place for a quiet getaway."

includes taxes & fees

26 Aug - 27 Aug

2 Bedroom Aqua Lodge # 13 Barracuda | Living area

"I love ❤️ this place "

Suite, 1 Bedroom, Kitchen, Sea Facing | Beach/ocean view

"Very nice place."

includes taxes & fees

26 Aug - 27 Aug

"We only stayed one night but it was nice and we enjoyed ourselves."

includes taxes & fees

10 Aug - 11 Aug

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

includes taxes & fees

2 Aug - 3 Aug

"Good to stay for a night ! "

includes taxes & fees

10 Aug - 11 Aug

"Nice place "

includes taxes & fees

20 Aug - 21 Aug

Daily cooked-to-order breakfast for a fee

"Amazing place to stay! "

includes taxes & fees

3 Aug - 4 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

12 Aug - 13 Aug

includes taxes & fees

26 Aug - 27 Aug

includes taxes & fees

11 Aug - 12 Aug

includes taxes & fees

11 Aug - 12 Aug

"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"

includes taxes & fees

11 Aug - 12 Aug

Save an average of 15% on thousands of hotels when you're signed in

Our guide on where to stay in Cutthroat Harbor Estates

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

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

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 Venture Out Keys.

See properties

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Newfound Harbor Keys and Cook Island.

See properties

Top Cutthroat Harbor Estates Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"We stayed for July 4th and it was perfect! Loved the suite and as a family it was very convenient to have a kitchen, washer and dryer! "

Beachside Resort & Residences

10/10 Excellent

"We were here with our family (party of 10). Some of the reviews had me nervous after booking but honestly we had zero issues. Everything was beautiful and clean, staff was amazing! We were right on the pool and had zero issue with late night noise. Parking was super convenient in garages right under your rooms. We loved being able to take the shuttle although if going in the evening, be sure to arrive early to get on the shuttle back so your party doesn’t split. Ours didn’t all fit on in the evening but we sent a mom and all the kids on one and then the dads and older kids took an uber back and actually made it back before us. We will definitely be back and hope to get a chance to try Tavern on the Town restaurant. It smelled SO good!"

Hampton Inn Key West FL

10/10 Excellent

"Perfect hotel kinda on the other side of the main area of key west but island is so small it still feels close. Theirs a shuttle that runs every 45 minutes sign up in lobby asap! We rented a golf cart from hotel that was so convenient. Its every close to keywest Airport which was so cool watching the planes fly over while in the pool especially when the sea plane fly over it make you really feel like your on a island in the middle of nowhere! The rooms are spacious the bathroom are very nice! Get a room with a pool view second floor with balcony its worth it! Staff was very friendly at front desk. Perks are you get a drink card with 2 free drinks pre day from pool bar! We will definitely stay here again... "

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Hotels Near Summerland Key, Florida

Hotels near popular Summerland Key Attractions

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Cutthroat Harbor Estates Hotels, Summerland Key

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cutthroat Harbor Estates

Check prices for these dates

Filter by

1355 Cheap Hotels in Cutthroat Harbor Estates - Specials, Reviews, & Last Minute Deals

Barnacle Resort

Barnacle Resort

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Parmer's Resort

Parmer's Resort

Looe Key Reef Resort

Looe Key Reef Resort

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

Sugar Loaf Lodge

Sugar Loaf Lodge

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House

New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House

Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House

Evershore House Pool Parking Dock

Evershore House Pool Parking Dock

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House

Aquaria House by Brightwild Pool Boat Dock

Aquaria House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock

Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool

Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock

Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool

Our guide on where to stay in Cutthroat Harbor Estates

Sugarloaf Shores

Cudjoe Gardens

Breezeswept Beach Estates

Top Cutthroat Harbor Estates Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Hotels Near Summerland Key, Florida

Hotels near popular Summerland Key Attractions

More accommodation types in Cutthroat Harbor Estates

Accommodation Near Summerland Key, Florida

Explore more hotels

More ways to book

Expedia's Latest Trends

Frequently asked questions