The Best Hotels Closest to Squirrel Key in Summerland Key for 2026

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Our top choices for Squirrel Key hotels

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

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. Sugar Loaf Lodge

6.8 km from Squirrel Key

morgan

￥18,812

￥21,164 total

includes taxes & fees

Oct 18 - Oct 19

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

A concrete pathway flanked by lush green foliage, leading to a shaded area.

A large house with a pool, surrounded by lush greenery.

A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

2. Atlantic View Luxury Villa with Pool

12.4 km from Squirrel Key

Preetam

￥81,806

￥154,276 total

includes taxes & fees

Oct 18 - Oct 19

A wooden deck with a railing, wicker chairs, and a view of greenery.

A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.

A two-story house with a balcony and a staircase leading to the upper level.

A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.

3. Starlight Serenity - Hideaway w Stunning Views

8.8 km from Squirrel Key

max

￥47,627

￥108,354 total

includes taxes & fees

Oct 27 - Oct 28

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

A breakfast setting with a table, chairs, a vase with flowers, and a city view.

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

A clear view of turquoise ocean water and a blue sky with clouds.

4. Hilton Key West Resort & Marina

16.5 km from Squirrel Key

Eric A

￥19,340

￥31,005 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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.

5. The Perry Hotel & Marina Key West

17 km from Squirrel Key

Jade

￥22,105

￥34,614 total

includes taxes & fees

Oct 30 - Oct 31

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

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.

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

6. Hampton Inn Key West FL

18.6 km from Squirrel Key

Erika

￥26,716

￥30,056 total

includes taxes & fees

Oct 25 - Oct 26

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

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A resort with a well-maintained lawn, palm trees, a pool area, 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.

7. Hyatt Vacation Club at Windward Pointe, Key West

18.8 km from Squirrel Key

Tina

￥27,038

￥37,532 total

includes taxes & fees

Oct 27 - Oct 28

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

A beach with palm trees, clear blue water, and a pier extending into the sea.

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.

8. Beachside Resort & Residences

17.6 km from Squirrel Key

Mollie

￥18,492

￥35,921 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

9. Hyatt Vacation Club at Beach House, Key West

17.4 km from Squirrel Key

￥36,991

￥48,729 total

includes taxes & fees

Oct 29 - Oct 30

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

A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.

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

A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.

10. DoubleTree Resort by Hilton Grand Key - Key West

18.2 km from Squirrel Key

Nancy

￥18,843

￥26,533 total

includes taxes & fees

Oct 27 - Oct 28

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

A wooden dock with a table and chairs, a table lamp, and a toaster.

Three floating cabins with balconies, named Aqua-Lodge, docked on calm water with a clear sky and trees in the background.

A marina with boats docked, a restaurant with outdoor seating, and a building with a blue roof.

11. Aqua Lodges at Hurricane Hole Marina

17.2 km from Squirrel Key

Kagni

￥23,938

￥54,236 total

includes taxes & fees

Oct 28 - Oct 29

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 multi-story hotel with balconies and a well-lit entrance.

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.

12. The Laureate Key West

18.1 km from Squirrel Key

Eileen

￥25,135

￥32,725 total

includes taxes & fees

Oct 18 - Oct 19

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

An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

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.

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

17.7 km from Squirrel Key

Brian

￥21,199

￥28,294 total

includes taxes & fees

Oct 25 - Oct 26

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

A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.

14. Grand Marina Suite by Brightwild Waterfront

16.2 km from Squirrel Key

Pawel

￥51,301

￥96,126 total

includes taxes & fees

Oct 19 - Oct 20

A swimming pool with lounge chairs and palm trees.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

A modern living room with a sectional sofa, a small round table, and a potted plant.

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

15. Hilton Garden Inn Key West / The Keys Collection

17.7 km from Squirrel Key

Eli

￥16,789

￥23,341 total

includes taxes & fees

Oct 28 - Oct 29

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

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

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

16. Blue Flamingo Resort Key West

17.7 km from Squirrel Key

Esteban

￥19,776

￥31,140 total

includes taxes & fees

Oct 25 - Oct 26

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

A modern restaurant with a wooden counter, seating area, and large windows.

A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

17. Courtyard by Marriott Key West Waterfront

19.1 km from Squirrel Key

Everton

￥27,487

￥30,922 total

includes taxes & fees

Oct 26 - Oct 27

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

A beach with palm trees, lounge chairs, and umbrellas.

A tall palm tree with a white building in the background.

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

18. Parrot Key Hotel & Villas

19.5 km from Squirrel Key

Anthony

￥24,028

￥36,102 total

includes taxes & fees

Oct 29 - Oct 30

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

A marina with boats docked, a beach resort building, and palm trees.

19. Ibis Bay Beach Resort

19.1 km from Squirrel Key

Andre

￥21,511

￥29,300 total

includes taxes & fees

Oct 18 - Oct 19

A coastal hotel with multiple buildings, a swimming pool, and a marina with boats.

A lobby with a reception desk, a bar area, and a sign that reads "Tavern Town".

20. Resort View 1BR Suite

17.5 km from Squirrel Key

Michael

￥34,286

￥52,514 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Compare popular hotels close to Squirrel Key

Property	Star rating	Guest rating
Sugar Loaf Lodge	8.2 Very good 1,000 reviews	View
Atlantic View Luxury Villa with Pool	7.4 Good 3 reviews	View
Starlight Serenity - Hideaway w Stunning Views	10.0 Exceptional 1 review	View
Hilton Key West Resort & Marina	9.0 Wonderful 1,793 reviews	View
The Perry Hotel & Marina Key West	9.4 Exceptional 1,307 reviews	View

Hotels recommended for families near Squirrel Key

Sugar Loaf Lodge

Summerland Key

￥18,812

￥21,164 total

includes taxes & fees

Oct 18 - Oct 19

Starlight Serenity - Hideaway w Stunning Views

Summerland Key

￥47,627

￥108,354 total

includes taxes & fees

Oct 27 - Oct 28

A two-story house with a balcony, a staircase, and a view of the beach.

A beach view with a swimming pool, palm trees, and lounge chairs.

A kitchen with a window, a sink, and wooden cabinets.

A beach with palm trees, a wooden dock, and lounge chairs.

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Cudjoe Key

￥51,376

￥115,221 total

includes taxes & fees

Oct 19 - Oct 20

Hilton Key West Resort & Marina

Stock Island

￥19,340

￥31,005 total

includes taxes & fees

Oct 25 - Oct 26

The Perry Hotel & Marina Key West

Stock Island

￥22,105

￥34,614 total

includes taxes & fees

Oct 30 - Oct 31

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

A resort with a swimming pool, beach area, and marina.

A coastal residential area with houses, a marina, and a flag.

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Cudjoe Key

￥19,752

￥65,319 total

includes taxes & fees

Oct 16 - Oct 17

An aerial view of a resort with a large pool, palm trees, and a pier.

A balcony with wicker furniture, a wooden table, and a view of the surrounding area.

A modern kitchen with a central island, bar stools, a refrigerator, and a seating area with a sofa and chairs.

A two-story building with a balcony, a covered entrance, and a parking area with a bicycle.

Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key

￥55,328

￥109,510 total

includes taxes & fees

Oct 27 - Oct 28

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Cudjoe Key

￥31,537

￥80,632 total

includes taxes & fees

Oct 21 - Oct 22

Top Squirrel Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

10/10 Excellent

"Friendly and helpful staff from the moment we entered the Sugarloaf KOA property (Thanks Elizabeth). It was so nice to come back to a cool and clean 2 bedroom cottage after a fun filled day of water activities. It was perfect for our family of 5."

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"I cannot say enough good things about this property. The staff is incredibly friendly and helpful. The amenities are great and the hotel itself is very clean and fairly modern. We had three teenagers with us and we had a blast every day. We had bad weather, but there were still so many things to see and do in the area. The wildlife is so fun. There’s a whole family of Stone crabs that live behind the marina. There are tons of fish in the water to go visit every day. It was just so much fun. I’ve never stayed at a KOA campground or hotel before and was beyond pleasantly surprised."

Sugar Loaf Lodge

8/10 Good

"Balcony"

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Everything was great! The house and the pool were clean and the basketball goal was an added plus! We wished that there were pool/beach towels in the house, but other than that everything was perfect!"

Oceanside, pet friendly, smart home with plenty of paddle equipment

10/10 Excellent

"nice location, lovely atmosphere in neighborhood"

Fandango - private pool <br>This is a pet friendly home. A pet fee and approval of your pet is required.

8/10 Good

"Overall the house worked well for what we wanted. Like the proximity to Key West and a great area for a small boat to explore the backcountry from. Being critical, it could have been cleaner and it’s due for a remodel"

Private and Exclusive Florida Keys Getaway

10/10 Excellent

"Beautiful view and sweet natural beach/coastline. The pool was heavenly"

Starlight Serenity - Hideaway with Stunning Views

10/10 Excellent

"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

10/10 Excellent

"This was a lovely home and there was great communication with the host."

Other attractions near Squirrel Key

Upper Sugarloaf Sound

9.2/10 (17 reviews)

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

See properties

Frequently asked questions

What's the area like around Squirrel Key?

Squirrel Key is located in Summerland Key. You'll find 39 hotels and other accommodations within a few miles for a convenient home base.

What's the best hotel to stay close to Squirrel Key?

Sugar Loaf Lodge is one of the top choices for your stay based on our traveler data, and this hotel offers a marina and a restaurant. It's located 4.2 mi (6.8 km) from Squirrel Key. Other good options around the area include Sugarloaf Key RV Resort & Cottages and Sugarloaf Key Hotel at KOA Resort.

How many hotels should I expect to find near Squirrel Key?

Expedia has 39 hotels and other accommodations a few miles from Squirrel Key.

If I need to cancel the hotel reservation for my stay near Squirrel Key, will I receive a refund?

Yes, you'll find most hotel bookings are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to cancel it and receive a refund within 24 hours of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to view the best options available near Squirrel Key.

Where can I learn more about changing or cancelling my trip in the area near Squirrel Key?

For more details about rescheduling or cancelling your stay near Squirrel Key, go to https://www.expedia.com/service/.

Find hotels near Squirrel Key, Summerland Key from ￥21,164

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Property class

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Our top choices for Squirrel Key hotels

1. Sugar Loaf Lodge

2. Atlantic View Luxury Villa with Pool

3. Starlight Serenity - Hideaway w Stunning Views

4. Hilton Key West Resort & Marina

5. The Perry Hotel & Marina Key West

6. Hampton Inn Key West FL

7. Hyatt Vacation Club at Windward Pointe, Key West

8. Beachside Resort & Residences

9. Hyatt Vacation Club at Beach House, Key West

10. DoubleTree Resort by Hilton Grand Key - Key West

11. Aqua Lodges at Hurricane Hole Marina

12. The Laureate Key West

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

14. Grand Marina Suite by Brightwild Waterfront

15. Hilton Garden Inn Key West / The Keys Collection

16. Blue Flamingo Resort Key West

17. Courtyard by Marriott Key West Waterfront

18. Parrot Key Hotel & Villas

19. Ibis Bay Beach Resort

20. Resort View 1BR Suite

Compare popular hotels close to Squirrel Key

Hotels recommended for families near Squirrel Key

Sugar Loaf Lodge

Starlight Serenity - Hideaway w Stunning Views

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Hilton Key West Resort & Marina

The Perry Hotel & Marina Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Spanish Queen @Venture Out, Cudjoe Key

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Top Squirrel Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key Hotel at KOA Resort

Sugar Loaf Lodge

Private Secluded Ocean View & Pool Near Key West

Oceanside, pet friendly, smart home with plenty of paddle equipment

Fandango - private pool <br>This is a pet friendly home. A pet fee and approval of your pet is required.

Private and Exclusive Florida Keys Getaway

Starlight Serenity - Hideaway with Stunning Views

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

Other attractions near Squirrel Key

Upper Sugarloaf Sound

Frequently asked questions