Squirrel Key Tours

Plan a trip to see Squirrel Key

Price found within the past 48 hours. Click for updated prices.
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,624, price is now $666 per person
$666
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
19.2/10 Exceptional! (53 reviews)
Lovely property. Staff service inconsistent overall. Room was not serviced one day. On the day there was construction above pool area, no notice was sent out. Pool area staff/manager and construction crew didn't seem to be on the same page.

Reviewed on Nov 13, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,997, price is now $760 per person
$760
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16/10 Exceptional! (1,004 reviews)
Room was clean and spacious. Property did not have available microwave for guest. House keeping was good but did not replace soap or drinking glass. Gym not located in main hotel area and it closes at 5pm. Overall property is beautiful and good amenities.

Reviewed on Nov 7, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $16,768, price is now $7,492 per person
$7,492
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
16/10 Exceptional! (1 review)

Popular places to visit

Upper Sugarloaf Sound

Upper Sugarloaf Sound

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

Upper Sugarloaf Sound
Shark Key

Shark Key

Commune with nature and explore the great outdoors at Shark Key during your travels in Key West. In the area, take in the great live music and beautiful sunsets.

Shark Key
South Beach which includes a beach and a coastal town as well as a large group of people

Florida Keys Beaches

4/5(519 reviews)

Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?

Florida Keys Beaches

Halfmoon Key

Commune with nature and explore the great outdoors at Halfmoon Key during your travels in Key West. Discover the area's great live music, or seek out its biking trails.

Halfmoon Key

Wilhelmina Harvey Park

Explore the great outdoors at Wilhelmina Harvey Park, a lovely green space in Key West.

Wilhelmina Harvey Park

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Best Lodging Options Near Squirrel Key

Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
Sugar Loaf Lodge
Sublimely private luxury home with enveloping oceanfront views near Key West

Sublimely private luxury home with enveloping oceanfront views near Key West

Near Key West
Sublimely private luxury home with enveloping oceanfront views near Key West
34’ Catamaran Sailboat

34’ Catamaran Sailboat

Key West
34’ Catamaran Sailboat
Florida Keys Beach Getaway

Florida Keys Beach Getaway

Upper Sugarloaf Key
Florida Keys Beach Getaway
Beach Getaway in the Florida Keys

Beach Getaway in the Florida Keys

SUGARLOAF KEY
Beach Getaway in the Florida Keys
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
Sugarloaf Key Hotel at KOA Resort
Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

Summerland Key
Private Secluded Ocean View & Pool Near Key West
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Ocean View 4/2 Estate with Private Pool 15 minutes from Key West

Cudjoe Key FL
Ocean View 4/2 Estate with Private Pool 15 minutes from Key West
Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

3.5 out of 5
125 Colson Dr Summerland Key FL
Atlantic View Luxury Villa with Pool
See all 1,199 properties in Squirrel Key
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.