Book a hotel near Squirrel Key, Summerland Key

Top hotels close to Squirrel Key

Sugar Loaf Lodge

17001 Overseas Hwy Summerland Key FL

Free Cancellation

Reserve now, pay when you stay

4.2 mi from Squirrel Key

$119 nightly

$134 total

Aug 25 - Aug 26

Total with taxes and fees

This hotel features a marina, 2 outdoor tennis courts, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. A bar/lounge and a garden are also provided.

Pool

Parking included

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Key West FL

4.32 mi from Squirrel Key

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This vacation home features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

Pool

Hot Tub

Key West Beach House with heated pool, tiki, and dock.♿︎

Key West FL

4.42 mi from Squirrel Key

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A gym is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.

Pool

Kitchen

Sublimely private luxury home with enveloping oceanfront views near Key West

Sugarloaf Key FL

5.34 mi from Squirrel Key

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This vacation home includes a garden and barbecue grills.

Pool

Kitchen

Starlight Serenity - Hideaway with Stunning Views

Summerland Key FL

5.46 mi from Squirrel Key

$511 nightly

$567 total

Aug 25 - Aug 26

Total with taxes and fees

This vacation home features a water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

INFINITE HORIZONS Waterfront Home & Pool + Last Key White Glove Service...

Key West FL

5.7 mi from Squirrel Key

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Laundry facilities, concierge services, and barbecue grills are available at this vacation home.

Pool

Kitchen

Private and Exclusive Florida Keys Getaway

Upper Sugarloaf Key FL

6.16 mi from Squirrel Key

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

The Hemingway - Beach Houses Key West

Upper Sugarloaf Key FL

6.16 mi from Squirrel Key

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Florida Keys Beach Getaway

Sugarloaf Key FL

6.19 mi from Squirrel Key

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Private and Exclusive Beach Getaway

Sugarloaf Key FL

6.2 mi from Squirrel Key

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A gym is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Beach Getaway in the Florida Keys

SUGARLOAF KEY FL

6.21 mi from Squirrel Key

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This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Sugarloaf Key RV Resort & Cottages

311 Johnson Rd Summerland Key FL

6.49 mi from Squirrel Key

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An outdoor pool, free self parking, and laundry facilities are featured at this vacation home. WiFi in public areas is free. Luggage storage is also provided.

Pool

Pet friendly

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Squirrel Key hotels essential information

Accommodation	1,176 hotels
Lowest Price	$134
Highest Price	$567
Popular hotels	Sugar Loaf Lodge, Luxurious Oceanfront 5BR Property with heated Pool & Waterfall, Key West Beach House with heated pool, tiki, and dock.♿︎, Sublimely private luxury home with enveloping oceanfront views near Key West, Starlight Serenity - Hideaway with Stunning Views, INFINITE HORIZONS Waterfront Home & Pool + Last Key White Glove Service..., Private and Exclusive Florida Keys Getaway, The Hemingway - Beach Houses Key West, Sugarloaf Key RV Resort & Cottages, Florida Keys Beach Getaway, Private and Exclusive Beach Getaway, Beach Getaway in the Florida Keys

Recent Squirrel Key hotel reviews by fellow wanderers

Sugar Loaf Lodge

5 out of 5

Posted less than an hour ago

Travelocity Verified Review

"Me gustaría más opciones como un regular desayuno"

A verified traveler stayed at Sugar Loaf Lodge

Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

5 out of 5

Posted 4 months ago

Travelocity Verified Review

"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!"

A verified traveler stayed at Luxurious Oceanfront 5BR Property with heated Pool & Waterfall

Starlight Serenity - Hideaway with Stunning Views

5 out of 5

Posted 4 months ago

Travelocity Verified Review

"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!"

A verified traveler stayed at Starlight Serenity - Hideaway with Stunning Views

Sublimely private luxury home with enveloping oceanfront views near Key West

5 out of 5

Posted 5 months ago

Travelocity Verified Review

"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."

A verified traveler stayed at Sublimely private luxury home with enveloping oceanfront views near Key West