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 corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

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

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

1. Sugar Loaf Lodge

4.2 mi from Squirrel Key

Marjorie

$119 nightly

$134 total

Sep 1 - Sep 2

Total with taxes and fees

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

A residential property with a swimming pool, a covered patio, and a view of the ocean.

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

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

2. Atlantic View Luxury Villa with Pool

7.7 mi from Squirrel Key

Preetam

$925 nightly

$1,041 total

Sep 9 - Sep 10

Total with taxes and fees

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

A modern kitchen with a large island, bar stools, and a dining area with a round table and chairs.

A spacious living room with a large flat-screen TV, a white sofa, two round coffee tables, and a dining area with a glass table and wicker chairs.

A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.

3. Starlight Serenity - Hideaway w Stunning Views

5.5 mi from Squirrel Key

max

$533 nightly

$600 total

Sep 7 - Sep 8

Total with taxes and fees

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.

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

4. Hilton Key West Resort & Marina

10.3 mi from Squirrel Key

Linda

$167 nightly

$188 total

Sep 7 - Sep 8

Total with taxes and fees

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

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with numerous yachts docked, surrounded by palm trees and a clear sky.

An outdoor seating area with tables and chairs, overlooking a marina with boats.

5. The Perry Hotel & Marina Key West

10.6 mi from Squirrel Key

Boyan

$199 nightly

$224 total

Sep 21 - Sep 22

Total with taxes and fees

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

A bar area with a thatched roof, wooden chairs, and a poolside view.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

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

6. Hampton Inn Key West FL

11.6 mi from Squirrel Key

Melisa

$139 nightly

$156 total

Sep 1 - Sep 2

Total with taxes and fees

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 beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

7. Hyatt Vacation Club at Windward Pointe, Key West

11.7 mi from Squirrel Key

Mauricio

$211 nightly

$237 total

Sep 14 - Sep 15

Total with taxes and fees

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 spacious living area with a large window, a dining table, and comfortable seating.

8. Hyatt Vacation Club at Beach House, Key West

10.8 mi from Squirrel Key

Kailey

$237 nightly

$266 total

Sep 2 - Sep 3

Total with taxes and fees

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

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

A modern office space with a reception desk, computer, and seating area.

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

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

11 mi from Squirrel Key

Fernando

$141 nightly

$159 total

Sep 20 - Sep 21

Total with taxes and fees

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

A hotel with a central courtyard, palm trees, and a fountain.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

10. DoubleTree Resort by Hilton Grand Key - Key West

11.3 mi from Squirrel Key

Jose

$144 nightly

$162 total

Sep 7 - Sep 8

Total with taxes and fees

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

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.

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

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

11. The Laureate Key West

11.3 mi from Squirrel Key

Jayce

$184 nightly

$207 total

Sep 1 - Sep 2

Total with taxes and fees

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

A modern dining area with a glass table, four chairs, and a ceiling fan.

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.

12. Beachside Resort & Residences

10.9 mi from Squirrel Key

Jerome

$192 nightly

$216 total

Sep 1 - Sep 2

Total with taxes and fees

A hotel with a large pool, multiple balconies, and palm trees.

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

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

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

13. Blue Flamingo Resort Key West

11 mi from Squirrel Key

Sabrina

$166 nightly

$187 total

Sep 1 - Sep 2

Total with taxes and fees

A swimming pool with lounge chairs and palm trees.

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

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

14. Hilton Garden Inn Key West / The Keys Collection

11 mi from Squirrel Key

Amanda

$135 nightly

$152 total

Sep 22 - Sep 23

Total with taxes and fees

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

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.

15. Havana Cabana at Key West

11.4 mi from Squirrel Key

Fabrizio

$195 nightly

$220 total

Sep 2 - Sep 3

Total with taxes and fees

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.

16. Grand Marina Suite by Brightwild Waterfront

10 mi from Squirrel Key

Pawel

$459 nightly

$516 total

Sep 13 - Sep 14

Total with taxes and fees

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

A wooden deck with a table and chairs, overlooking a calm water body with boats and a house in the background.

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

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

17. Aqua Lodges at Hurricane Hole Marina

10.7 mi from Squirrel Key

Kagni

$238 nightly

$268 total

Sep 1 - Sep 2

Total with taxes and fees

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 hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

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

18. Courtyard by Marriott Key West Waterfront

11.9 mi from Squirrel Key

Everton

$174 nightly

$195 total

Sep 29 - Sep 30

Total with taxes and fees

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

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.

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

19. Parrot Key Hotel & Villas

12.1 mi from Squirrel Key

Melvin

$214 nightly

$241 total

Sep 14 - Sep 15

Total with taxes and fees

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

A pool area with blue lounge chairs, a hot tub, and a covered seating area.

20. Ibis Bay Beach Resort

11.8 mi from Squirrel Key

Roland

$136 nightly

$153 total

Sep 1 - Sep 2

Total with taxes and fees

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 1,832 reviews	View
The Perry Hotel & Marina Key West	9.4 Exceptional 1,329 reviews	View

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"Me gustaría más opciones como un regular desayuno"

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

10/10 Excellent

"nice location, lovely atmosphere in neighborhood"

Florida Keys Beach Getaway

10/10 Excellent

"Man, this place was awesome. If it wasnt for the sea weed, we would never want or have a need to leave. Seaweed was thinning out towards the end of our trip, but man, this place was worth it. Tom, your a gem bud."

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Best house I’ve ever stayed in, would absolutely recommend for that city life getaway. Host made sure we had everything we needed!"

Private and Exclusive Florida Keys Getaway

10/10 Excellent

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

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

10/10 Excellent

"We had an absolutely incredible stay in the Florida Keys this spring! This home exceeded every expectation and was the perfect place for our group of friends and family to relax and enjoy island life. Cris was wonderful to work with — communication was prompt, friendly, and seamless from start to finish.The property was spotless, beautifully maintained, and thoughtfully stocked with everything we needed. The oceanfront setting was stunning, with peaceful mornings by the water and unforgettable sunsets at nearby waterfront restaurants. The outdoor spaces quickly became our favorite place to gather, relax, and soak in the laid-back Keys atmosphere.We loved kayaking from the property, swimming in the clear ocean water, and fishing from the dock. Playing pickleball nearby and walking to the local island coffee shop afterward became one of our favorite routines. The two-story layout with kitchens on both levels was perfect for our group, giving everyone plenty of space and privacy while still feeling connected.The location was ideal — close to restaurants and activities while still peaceful and private. This home created unforgettable memories for all of us, and we would return in a heartbeat. Highly recommend for the perfect Florida Keys getaway!"

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."

Sublimely private luxury home with enveloping oceanfront views near Key West

10/10 Excellent

"We had a wonderful stay at this home. The property itself is absolutely stunning, with beautiful sunset views and a great layout that made it easy for everyone to spread out and relax. The pool was warm and inviting, and there was plenty of space for our group to enjoy both indoors and outdoors. The party room was fun for our teenagers and adults! One of the highlights was the location on the bay—the water is very shallow and incredibly calm, which made it perfect for relaxing and enjoying the surroundings. However, if you’re looking for ocean waves, you won’t get that here. The bedrooms were a pleasant surprise. Although there were no photos listed, they were all very spacious and each had its own en-suite bathroom, which added a lot of comfort and convenience for our group.There were just a couple of things to note. The upstairs bathrooms had low water pressure, which could be improved. Additionally, only four exterior cameras were disclosed in the listing; however, we counted seven cameras around the exterior of the home. Full and accurate disclosure of all cameras is important, and this discrepancy made us feel uncomfortable at times—especially traveling with teenage daughters.Overall, this is a beautiful home in a great setting, and we truly enjoyed our stay."

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 38 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 38 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 $134

Upfront pricing

Treat yourself

Be picky

Check prices for these dates

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Star rating

Guest rating

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. Hyatt Vacation Club at Beach House, Key West

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

10. DoubleTree Resort by Hilton Grand Key - Key West

11. The Laureate Key West

12. Beachside Resort & Residences

13. Blue Flamingo Resort Key West

14. Hilton Garden Inn Key West / The Keys Collection

15. Havana Cabana at Key West

16. Grand Marina Suite by Brightwild Waterfront

17. Aqua Lodges at Hurricane Hole Marina

18. Courtyard by Marriott Key West Waterfront

19. Parrot Key Hotel & Villas

20. Ibis Bay Beach Resort

Compare popular hotels close to Squirrel Key

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

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

Florida Keys Beach Getaway

Private Secluded Ocean View & Pool Near Key West

Private and Exclusive Florida Keys Getaway

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Starlight Serenity - Hideaway with Stunning Views

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

Sublimely private luxury home with enveloping oceanfront views near Key West

Other attractions near Squirrel Key

Upper Sugarloaf Sound

Frequently asked questions