The Best Hotels Closest to Squirrel Key in Summerland Key - 2026 Updated Prices

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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

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

1. Sugar Loaf Lodge

4.2 mi from Squirrel Key

Richard

£101

includes taxes & fees

4 Oct - 5 Oct

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

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

A modern kitchen with a large island, white cabinetry, and three wicker bar stools.

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

2. Starlight Serenity - Hideaway w Stunning Views

5.5 mi from Squirrel Key

max

£465

includes taxes & fees

5 Oct - 6 Oct

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.

3. Hilton Key West Resort & Marina

10.3 mi from Squirrel Key

Molly

£152

includes taxes & fees

12 Oct - 13 Oct

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 balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

4. The Perry Hotel & Marina Key West

10.6 mi from Squirrel Key

Jade

£146

includes taxes & fees

26 Oct - 27 Oct

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

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

5. Hampton Inn Key West FL

11.6 mi from Squirrel Key

Jaycie

£141

includes taxes & fees

7 Oct - 8 Oct

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

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

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.

6. Beachside Resort & Residences

10.9 mi from Squirrel Key

James

£147

includes taxes & fees

4 Oct - 5 Oct

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

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

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

An outdoor patio with tables and chairs, umbrellas, and palm trees.

7. DoubleTree Resort by Hilton Grand Key - Key West

11.3 mi from Squirrel Key

Nancy

£131

includes taxes & fees

11 Oct - 12 Oct

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

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

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 hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

8. The Laureate Key West

11.3 mi from Squirrel Key

Mailyn

£157

includes taxes & fees

4 Oct - 5 Oct

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

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

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

9. Blue Flamingo Resort Key West

11 mi from Squirrel Key

Esteban

£143

includes taxes & fees

4 Oct - 5 Oct

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 hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

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

11 mi from Squirrel Key

Patricia

£131

includes taxes & fees

4 Oct - 5 Oct

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

11. Hilton Garden Inn Key West / The Keys Collection

11 mi from Squirrel Key

Walt

£116

includes taxes & fees

8 Oct - 9 Oct

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

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

12. Grand Marina Suite by Brightwild Waterfront

10 mi from Squirrel Key

Pawel

£495

includes taxes & fees

7 Oct - 8 Oct

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

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

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

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

13. Parrot Key Hotel & Villas

12.1 mi from Squirrel Key

Anthony

£156

includes taxes & fees

11 Oct - 12 Oct

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

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

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

14. Havana Cabana at Key West

11.4 mi from Squirrel Key

Gustavo

£155

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

15. Ibis Bay Beach Resort

11.8 mi from Squirrel Key

Stephanie

£133

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

16. Courtyard by Marriott Key West Waterfront

11.9 mi from Squirrel Key

Everton

£165

includes taxes & fees

26 Oct - 27 Oct

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

An outdoor bar area with a large island, bar stools, and a pool.

17. Resort View 1BR Suite

10.9 mi from Squirrel Key

Michael

£211

includes taxes & fees

6 Oct - 7 Oct

18. Island View 1BR Residence With Balcony

10.9 mi from Squirrel Key

Luis

£223

includes taxes & fees

6 Oct - 7 Oct

A beach view with palm trees, a wooden pier, and a sunset over the water.

19. Ocean Front 1BR Suite With Direct Beach Access

10.9 mi from Squirrel Key

Jacqueline

£265

includes taxes & fees

4 Oct - 5 Oct

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

A swimming pool with a green-roofed building, palm trees, and a clear blue sky.

A modern kitchen with a central island, bar stools, and a dining area with a lamp.

A compact kitchen with a central island, a dining area with wicker furniture, and a view of the outdoors.

20. The Grenada Suite Pool View Private Balcony

11.5 mi from Squirrel Key

Luis

£422

includes taxes & fees

5 Oct - 6 Oct

View all properties

Compare popular hotels close to Squirrel Key

Property	Property class	Guest rating
Sugar Loaf Lodge	8.2 Very good 1,000 reviews	View
Starlight Serenity - Hideaway w Stunning Views	10.0 Exceptional 1 review	View
Hilton Key West Resort & Marina	9.0 Wonderful 1,800 reviews	View
The Perry Hotel & Marina Key West	9.4 Exceptional 1,315 reviews	View
Hampton Inn Key West FL	9.0 Wonderful 1,539 reviews	View

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"

Sugarloaf Key RV Resort & Cottages

8/10 Good

"Nice for a chill weekend in the lower keys and for people with family accompanying them"

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Great host ! Few snags but it all worked out great."

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

10/10 Excellent

"nice location, lovely atmosphere in neighborhood"

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 39 hotels and other accommodations within a few miles for a convenient home base.

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

Sugar Loaf Lodge is one of the top choices for your stay based on our traveller data, and this hotel offers a marina and a restaurant. It's located 4.2 mi (6.8 km) from Squirrel Key. Other good choices 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 accommodation options 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, most room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a non-refundable reservation, it might still be possible to cancel it and get a refund within 24 hours of your booking. Plug in your dates, click on "Search", then use the filter option "fully refundable" to review top deals close to Squirrel Key.

Search Hotels Near Squirrel Key, Summerland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Squirrel Key hotels

1. Sugar Loaf Lodge

2. Starlight Serenity - Hideaway w Stunning Views

3. Hilton Key West Resort & Marina

4. The Perry Hotel & Marina Key West

5. Hampton Inn Key West FL

6. Beachside Resort & Residences

7. DoubleTree Resort by Hilton Grand Key - Key West

8. The Laureate Key West

9. Blue Flamingo Resort Key West

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

11. Hilton Garden Inn Key West / The Keys Collection

12. Grand Marina Suite by Brightwild Waterfront

13. Parrot Key Hotel & Villas

14. Havana Cabana at Key West

15. Ibis Bay Beach Resort

16. Courtyard by Marriott Key West Waterfront

17. Resort View 1BR Suite

18. Island View 1BR Residence With Balcony

19. Ocean Front 1BR Suite With Direct Beach Access

20. The Grenada Suite Pool View Private Balcony

Compare popular hotels close to Squirrel Key

Top Squirrel Key Hotel Reviews

Sugar Loaf Lodge

Sugarloaf Key RV Resort & Cottages

Private Secluded Ocean View & Pool Near Key West

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

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