Hotels in Summerland Key

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Looe Key Reef Resort
Looe Key Reef Resort
2.5 star property
Summerland Key
7.4 out of 10, Good, (1,001 reviews)
The price is $140
$158 total
includes taxes & fees
Jan 29 - Jan 30
Looe Key Reef Resort
Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
  • cleanliness
    Waterfront villa with 10 pools on tranquil Summerland Key, minutes from beaches.
The price is $616
$1,087 total
includes taxes & fees
Jan 21 - Jan 22
Atlantic View Luxury Villa with Pool
Parmer's Resort
Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,001 reviews)
The price is $254
$318 total
includes taxes & fees
Jan 19 - Jan 20
Parmer's Resort
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is $359
$757 total
includes taxes & fees
Jan 28 - Jan 29
Starlight Serenity - Hideaway w Stunning Views
Sugar Loaf Lodge
Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1,001 reviews)
The price is $199
$224 total
includes taxes & fees
Jan 19 - Jan 20
Sugar Loaf Lodge
Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (287 reviews)
  • cleanliness
    Waterfront escape with a marina, outdoor pool, and easy access to Florida Keys Beaches.
The price is $149
$308 total
includes taxes & fees
Jan 28 - Jan 29
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
Sunshine Key RV Resort & Marina
2.0 star property
Big Pine Key
8.8 out of 10, Excellent, (160 reviews)
The price is $365
$411 total
includes taxes & fees
Jan 28 - Jan 29
Sunshine Key RV Resort & Marina
Waterfront Luxury Home - Tidelands House
Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
  • cleanliness
    Secluded garden retreat near Duval Street and Key West's famous beaches.
The price is $1,884
$3,146 total
includes taxes & fees
Jan 18 - Jan 19
Waterfront Luxury Home - Tidelands House
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
Stock Island
9.0 out of 10, Wonderful, (1,776 reviews)
  • cleanliness
    Relax in a luxurious marina getaway with six outdoor pools and Key West views.
The price is $267
$362 total
includes taxes & fees
Jan 21 - Jan 22
Oceans Edge Key West Resort, Hotel & Marina
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (172 reviews)
  • cleanliness
    Floating marina oasis puts you minutes from Duval Street and Smathers Beach.
The price is $169
$358 total
includes taxes & fees
Jan 21 - Jan 22
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,002 reviews)
  • cleanliness
    Embrace oceanfront luxury at this Key West retreat with a bar and hot tub.
The price is $463
$566 total
includes taxes & fees
Feb 16 - Feb 17
Hyatt Vacation Club at Beach House, Key West
Knight's Key Suites
Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,164 reviews)
  • cleanliness
    Relaxing aparthotel near Sombrero Beach with pool and premium comforts.
The price is $138
$177 total
includes taxes & fees
Jan 19 - Jan 20
Knight's Key Suites
The Laureate Key West
The Laureate Key West
3.5 star property
New Town
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Explore the tropical haven minutes from Hemingway's home and Duval Street.
The price is $299
$365 total
includes taxes & fees
Jan 19 - Jan 20
The Laureate Key West
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key West
3.5 star property
Key West
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Oceanfront condo hotel with resort pool just minutes from Smathers Beach.
The price is $492
$599 total
includes taxes & fees
Feb 5 - Feb 6
Hyatt Vacation Club at Windward Pointe, Key West
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West
4.0 star property
New Town
8.0 out of 10, Very Good, (1,864 reviews)
  • cleanliness
    Paradise awaits at this Key West hotel, featuring 2 outdoor pools and poolside bars.
The price is $314
$410 total
includes taxes & fees
Jan 19 - Jan 20
Blue Flamingo Resort Key West
Beachside Resort & Residences
Beachside Resort & Residences
3.5 star property
Key West
8.6 out of 10, Excellent, (1,911 reviews)
  • cleanliness
    Beachside escape with private shoreline, two restaurants, and scenic ocean views.
The price is $285
$416 total
includes taxes & fees
Jan 19 - Jan 20
Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection
3.5 star property
New Town
8.0 out of 10, Very Good, (1,187 reviews)
  • cleanliness
    Unwind poolside in Key West with convenient access to Duval Street and beaches.
The price is $319
$387 total
includes taxes & fees
Jan 19 - Jan 20
Hilton Garden Inn Key West / The Keys Collection
Grand Marina Suite by Brightwild Waterfront
Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
  • cleanliness
    Experience Key West waterfront living with short drives to Duval and Smathers Beach.
The price is $554
$879 total
includes taxes & fees
Jan 18 - Jan 19
Grand Marina Suite by Brightwild Waterfront
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1,193 reviews)
  • cleanliness
    Bask in waterfront marina luxury with two pools and seafood dining on Stock Island.
The price is $363
$471 total
includes taxes & fees
Jan 21 - Jan 22
The Perry Hotel & Marina Key West
Captain Pips Marina & Hideaway
Captain Pips Marina & Hideaway
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Marina-side escape with outdoor pool and free bicycles near Sombrero Beach.
The price is $134
$179 total
includes taxes & fees
Jan 20 - Jan 21
Captain Pips Marina & Hideaway
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.

When is the best time to visit Summerland Key?

Our prices for hotels in Summerland Key are cheapest in September
Price trends for hotels in Summerland Key
Pricing is based on two traveler single night rates
View properties in January

Top neighborhoods in Summerland Key

Cutthroat Harbor Estates

Escape the tourist rush at Cutthroat Harbor Estates, a peaceful slice of paradise on Summerland Key. This residential waterfront neighborhood offers crystal-clear waters perfect for fishing, kayaking, and boating from your private dock. The low-rise coastal homes on stilts create a genuine Keys atmosphere where you can spot tropical birds and enjoy breathtaking sunset views. You'll need to drive to nearby Cudjoe Key or Summerland Key for dining options featuring fresh seafood and Caribbean flavors. Vacation rental homes with waterfront views dominate accommodation choices. The neighborhood's layout prioritizes privacy and seclusion, making it ideal for travelers seeking the authentic Florida Keys lifestyle.

Sugarloaf Shores

Sugarloaf Shores delivers waterfront paradise without the tourist crowds. Private canals weave between stilted homes where you can launch kayaks right from your rental's backyard dock. The crystal-clear backcountry waters beckon with world-class fishing, while gentle waves provide perfect spots for swimming and snorkeling. Dining and shopping require a short drive, as this peaceful residential enclave focuses on natural beauty rather than commercial offerings. Most visitors stay in spacious vacation homes with private pools and boat docks. A rental car is essential for exploring the rest of the Florida Keys from this secluded waterfront haven.

Cudjoe Gardens

Cudjoe Gardens offers a slice of authentic Florida Keys living with canal-front homes where you can park your boat right out back. This peaceful residential retreat lets you escape the crowds while still having easy access to the surrounding waters. Wildlife enthusiasts will spot herons stalking the shallows and fish jumping at sunrise while the gentle sound of water lapping against docks creates your vacation soundtrack. Nearby restaurants in Summerland Key and Cudjoe Key serve up fresh seafood just a short drive away. Most homes feature private pools, boat docks, and tropical landscaping, all designed for relaxation and water activities. A rental car is essential for exploring the area, as this quiet community focuses on waterfront living rather than tourist amenities.

Breezeswept Beach Estates

Breezeswept Beach Estates is a slice of Florida Keys paradise where private docks and waterfront homes replace tourist traps. You'll spend your days exploring crystal-clear waters, spotting marine life while kayaking, or casting a line into the Gulf. The surrounding Newfound Harbor Keys and nearby islands offer perfect day-trip adventures when you're ready to venture beyond your peaceful retreat. Vacation rentals with tropical landscaping and breezy porches make up the accommodation options here. You'll need a car to reach restaurants on Ramrod Key or stock up on groceries for cooking. The quiet streets and gentle waves create the perfect soundtrack for stargazing and disconnecting from the everyday hustle.

Learn more about Summerland Key

Summerland Key is well-known for its attractions such as Florida Keys Beaches and Sugarloaf Beach.

Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.

Check out reviews of Summerland Key hotels guests love

Frequently asked questions

What accommodations do travelers like in Summerland Key?
Sugarloaf Key Hotel at KOA Resort, Parmer's Resort and Sugar Loaf Lodge are all accommodations that are popular with guests.
Can I book a refundable hotel in Summerland Key?
If you're looking for the flexibility to change your travel plans to Summerland Key, most properties offer refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Summerland Key if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, look over our selection of 485 vacation homes. You can also consider one of 9 villas or 53 cottages for your stay.
What will the weather in Summerland Key be like during my trip?
Summerland Key is a great place to visit any time of year with an average temperature of 73°F during the coldest months.
Why should I book my Summerland Key hotel with Hotels.com?
There are lots of reasons to book your Summerland Key trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.