Hotels in Summerland Key

Sun, Feb 22
Tue, Feb 24
February 2026
21
March 2026

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Tonight
Feb 21 - Feb 22
Tomorrow
Feb 22 - Feb 23
Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8

Where to stay in Summerland Key?

Looe Key Reef Resort
Looe Key Reef Resort
Summerland Key
$140 nightly
$158 total
Mar 24 - Mar 25
Total with taxes and fees
Looe Key Reef Resort
Parmer's Resort
Parmer's Resort
Summerland Key
$334 nightly
$376 total
Mar 23 - Mar 24
Total with taxes and fees
Parmer's Resort
Atlantic View Luxury Villa with Pool
Atlantic View Luxury Villa with Pool
Summerland Key
  • Waterfront villa with 10 pools on tranquil Summerland Key, minutes from beaches.
$975 nightly
$1,097 total
Feb 22 - Feb 23
Total with taxes and fees
Atlantic View Luxury Villa with Pool
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway w Stunning Views
Summerland Key
$821 nightly
$924 total
Mar 12 - Mar 13
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views
Sugar Loaf Lodge
Sugar Loaf Lodge
Summerland Key
$299 nightly
$336 total
Feb 22 - Feb 23
Total with taxes and fees
Sugar Loaf Lodge
Old Wooden Bridge Resort and Marina
Old Wooden Bridge Resort and Marina
Punta Brisa
  • Waterfront escape with a marina, outdoor pool, and easy access to Florida Keys Beaches.
$358 nightly
$403 total
Feb 23 - Feb 24
Total with taxes and fees
Old Wooden Bridge Resort and Marina
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
Stock Island
  • Relax in a luxurious marina getaway with six outdoor pools and Key West views.
$410 nightly
$461 total
Mar 24 - Mar 25
Total with taxes and fees
Oceans Edge Key West Resort, Hotel & Marina
Grand Marina Suite by Brightwild Waterfront
Grand Marina Suite by Brightwild Waterfront
Stock Island
  • Experience Key West waterfront living with short drives to Duval and Smathers Beach.
$806 nightly
$907 total
Mar 1 - Mar 2
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
Aqua Lodges at Hurricane Hole Marina
Aqua Lodges at Hurricane Hole Marina
Stock Island
  • Floating marina oasis puts you minutes from Duval Street and Smathers Beach.
$355 nightly
$400 total
Mar 8 - Mar 9
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Beach House, Key West
Key West
  • Embrace oceanfront luxury at this Key West retreat with a bar and hot tub.
$536 nightly
$603 total
Mar 9 - Mar 10
Total with taxes and fees
Hyatt Vacation Club at Beach House, Key West
Knight's Key Suites
Knight's Key Suites
Marathon
  • Relaxing aparthotel near Sombrero Beach with pool and premium comforts.
$229 nightly
$255 total
Mar 8 - Mar 9
Total with taxes and fees
Knight's Key Suites
Beachside Resort & Residences
Beachside Resort & Residences
Key West
  • Beachside escape with private shoreline, two restaurants, and scenic ocean views.
$360 nightly
$405 total
Mar 1 - Mar 2
Total with taxes and fees
Beachside Resort & Residences
Blue Flamingo Resort Key West
Blue Flamingo Resort Key West
New Town
  • Paradise awaits at this Key West hotel, featuring 2 outdoor pools and poolside bars.
$373 nightly
$420 total
Mar 1 - Mar 2
Total with taxes and fees
Blue Flamingo Resort Key West
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key West
Key West
  • Oceanfront condo hotel with resort pool just minutes from Smathers Beach.
$511 nightly
$575 total
Mar 23 - Mar 24
Total with taxes and fees
Hyatt Vacation Club at Windward Pointe, Key West
Captain Pips Marina & Hideaway
Captain Pips Marina & Hideaway
Marathon
  • Marina-side escape with outdoor pool and free bicycles near Sombrero Beach.
$179 nightly
$202 total
Mar 1 - Mar 2
Total with taxes and fees
Captain Pips Marina & Hideaway
The Laureate Key West
The Laureate Key West
New Town
  • Explore the tropical haven minutes from Hemingway's home and Duval Street.
$404 nightly
$455 total
Mar 1 - Mar 2
Total with taxes and fees
The Laureate Key West
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
Stock Island
  • Bask in waterfront marina luxury with two pools and seafood dining on Stock Island.
$433 nightly
$487 total
Mar 2 - Mar 3
Total with taxes and fees
The Perry Hotel & Marina Key West
Hampton Inn Key West FL
Hampton Inn Key West FL
Key West
  • Unwind by the poolside just minutes from Smathers Beach and Key West's attractions.
$449 nightly
$505 total
Mar 4 - Mar 5
Total with taxes and fees
Hampton Inn Key West FL
Resort View 1BR Suite With Direct Pool Access
Resort View 1BR Suite With Direct Pool Access
Key West
  • Walk to Duval Street or kick back in the poolside suite near Key West's top beaches.
$496 nightly
$558 total
Mar 2 - Mar 3
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West
Key West
$381 nightly
$429 total
Mar 23 - Mar 24
Total with taxes and fees
DoubleTree Resort by Hilton Grand Key - Key West
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Our prices for hotels in Summerland Key are cheapest in August
Price trends for hotels in Summerland Key
Pricing is based on two traveler single night rates
View properties in February

Top neighborhoods in Summerland Key

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.

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.

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.

See all hotels in Summerland Key
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Ver nice , quiet stay highly recommend"
A Jeanette 4-night trip
Posted 3 days ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Clean room and great staff"
Paula 1-night trip
Posted 5 days ago
Sugar Loaf Lodge
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Excellent "
Arelis 2-night trip
Posted 6 days ago
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Great place ! Friendly staff "
Tom 1-night trip
Posted 2 weeks ago
Looe Key Reef Resort
Little Torch Cottages

Little Torch Cottages

10/10 Excellent
"Will return "
Vanessa 2-night trip
Posted 11 months ago
Little Torch Cottages

Frequently asked questions

How much does a hotel room cost in Summerland Key?
You can choose a great hotel in Summerland Key from $158 with properties to suit all budgets and needs. If you're after an affordable hotel in Summerland Key that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Summerland Key hotels?
Discover great deals on Summerland Key hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Summerland Key hotels.
Can I book Summerland Key hotels with free cancellation?
In order to book a refundable Summerland Key hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are the top-rated luxury hotels in Summerland Key?
One of the most popular luxury hotels in Summerland Key is Little Palm Island Resort & Spa - A Noble House Resort. Little Palm Island Resort & Spa - A Noble House Resort is a luxury resort with a high guest rating amongst our travelers, and it offers an outdoor pool, a full-service spa and scuba diving.
What are some top pet-friendly hotels in Summerland Key?
Our travelers' top pet-friendly hotels in Summerland Key include:You can also use the "Amenities" filter in your search on Hotels.com and check "Pet friendly" to discover more pet-friendly hotels in Summerland Key.
What are some of the best hotels in Summerland Key for couples?
Choose a top-rated Summerland Key romantic hotel and enjoy your couple's getaway. Our travelers love Little Palm Island Resort & Spa - A Noble House Resort, a resort with a private beach as well as in-room champagne service. Discover more hotels in Summerland Key on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".
What are the top Summerland Key hotels with a pool?
For a little extra luxury, discover some of the best Summerland Key hotels with a pool. Sugarloaf Key Hotel at KOA Resort is a great hotel with an outdoor pool and a guest rating of 9.8 out of 10. Plus, you can make the most of its private beach and hot tub. To find more stays in Summerland Key with a pool, use the "Amenities" filter on Hotels.com in your search and select "Pool".
What are some of the best Summerland Key hotels with free parking?
If you're driving, a great Summerland Key hotel with free parking is a bonus. Our travelers' favorites include:
What are some popular hotels in central Summerland Key?
If you're looking for hotels in central Summerland Key, check out Sugarloaf Key Hotel at KOA Resort. Travelers love Sugarloaf Key Hotel at KOA Resort for its location, as well as the private beach, outdoor pool and hot tub this hotel offers. Cutthroat Harbor Estates and Cudjoe Gardens are some of the most central neighborhoods for your Summerland Key vacation.
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 472 vacation homes. You can also consider one of 9 villas or 54 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.

Find out more about Summerland Key

Escape to Paradise: Discover the Hidden Gems of Summerland Key

Nestled in the enchanting Florida Keys, Summerland Key is a hidden gem that offers an idyllic blend of natural beauty and laid-back charm. This serene island escape boasts pristine beaches, crystal-clear waters, and vibrant coral reefs perfect for snorkeling and diving. Explore the nearby National Key Deer Refuge, where you can spot the adorable Key deer in their natural habitat. With its picturesque sunsets, cozy waterfront dining, and a welcoming community, Summerland Key is ideal for families, couples, and anyone seeking a tranquil getaway. Discover the essence of island life in this captivating slice of paradise.

Discover great hotels in Summerland Key

Summerland Key offers a variety of accommodations, from cozy vacation rentals to comfortable hotels. Visitors can enjoy beachfront properties with stunning views, charming inns, and laid-back motels, all providing easy access to the natural beauty and recreational activities of the Florida Keys. Here are some of the most popular hotels with our travelers in Summerland Key:

  1. Deer Run Bed & BreakfastOpens in a new window: This 2.5-star Bed and Breakfast hotel is ideal for leisure travelers seeking a beach vacation experience. With direct access to the beach, guests can enjoy sun-soaked days and tranquil evenings by the shore. The cozy atmosphere and personal touches create a welcoming environment that enhances relaxation. Visitors appreciate the intimate setting and the opportunity to unwind in a beautiful coastal location.
  2. Oceans Edge Key West ResortOpens in a new window: This 4.0-star hotel caters to adventure enthusiasts and business travelers alike, providing a well-rounded experience. With multiple meeting rooms and business facilities, the hotel also offers exciting adventure sports options, including onsite fishing, motorboating, and nearby parasailing. The blend of business amenities and recreational activities creates a dynamic environment, making it a top choice for those looking to balance work and play. Guests rave about the engaging atmosphere and the chance to explore thrilling activities right at their doorstep.
  3. The Perry Hotel & Marina Key WestOpens in a new window: This 4.0-star hotel is perfect for adventure seekers and LGBTQIA travelers. Offering a welcoming environment, the hotel features meeting rooms and conference spaces for those who require business facilities. Guests can take advantage of nearby bicycle rentals, parasailing, and windsurfing for a thrilling getaway. The vibrant atmosphere and inclusivity create an unforgettable experience, with many praising the diverse activities available to enhance their stay. This hotel stands out for its commitment to providing distinctive experiences in a supportive setting.

Top locations to stay in Summerland Key

In Bay Point, Cudjoe Key, and Little Torch Key, you'll find appealing options for your stay near Summerland Key. Bay Point offers stunning waterfront views and a serene atmosphere. Cudjoe Key is perfect for biking and exploring nature, while Little Torch Key is ideal for water activities and relaxation. For first-time visitors, Cudjoe Key is best suited for a memorable experience.

  1. Bay PointOpens in a new window: Bay Point is a fantastic spot for travelers looking to enjoy the serene beauty of the Florida Keys. Nestled along the water, it offers stunning views and a relaxed atmosphere perfect for unwinding. Here, you can indulge in various water activities like kayaking and paddleboarding. The nearby nature trails provide excellent opportunities for biking and observing local wildlife, making it a great choice for nature enthusiasts. Plus, the community vibe and easy access to local shops make it a convenient base to explore the surrounding areas.
  2. Cudjoe KeyOpens in a new window: Cudjoe Key is an idyllic destination that attracts those who love biking and outdoor exploration. With its picturesque landscapes and easy access to beautiful beaches, it's an excellent choice for those who want to soak in the sun. The area is also known for its vibrant local arts scene, showcasing unique cultural attractions. Whether you're exploring the scenic bike paths or enjoying the sunset at a nearby park, Cudjoe Key offers a laid-back charm that's hard to resist.
  3. Little Torch KeyOpens in a new window: Little Torch Key is a hidden gem perfect for those seeking a more relaxed and intimate experience in the Florida Keys. This area boasts beautiful resorts and quaint accommodations, making it ideal for a peaceful getaway. You can enjoy the local marine life through snorkeling or diving, and the calm waters are perfect for swimming. The charming surroundings offer a great escape from the hustle and bustle, allowing you to truly unwind and connect with nature.

Things to do in Summerland Key

Summerland Key, nestled in the Florida Keys, boasts stunning beaches and lush landscapes perfect for family fun. Enjoy boating, snorkeling in crystal-clear waters, or hiking through scenic nature trails. With vibrant shopping areas and relaxing resorts, this island paradise offers the ideal backdrop for unforgettable adventures and cherished memories.

  • Sugarloaf BeachOpens in a new window – Spend a relaxing day soaking up the sun on this beautiful beach, where the soft sands and gentle waves are perfect for families. Bring a picnic, build sandcastles, or simply enjoy the stunning views of the surrounding waters.
  • Upper Sugarloaf SoundOpens in a new window – Explore this picturesque island, where you can take in the serene beauty of the water and the lush landscapes. It's an ideal spot for kayaking or paddleboarding, providing a unique perspective of the vibrant marine life.
  • Upper Sugarloaf KeyOpens in a new window – Discover the charm of this quaint neighborhood. Enjoy a leisurely stroll, and take in the scenic views and local architecture that reflect the laid-back vibe of the Florida Keys.
  • Florida Keys BeachesOpens in a new window – Experience the quintessential beach life at one of the many stunning beaches in the area. From swimming to beach volleyball, there’s something for everyone to enjoy under the warm Florida sun.
  • Blue HoleOpens in a new window – Visit this unique lake, where you can spot various wildlife, including birds and fish. It’s a peaceful oasis, perfect for a quiet afternoon of nature watching or just unwinding by the water.

5 tips for savvy savings when booking a hotel in Summerland Key

  1. Book for the cheapest times: The most budget-friendly time to visit Summerland Key is from August to October, when hotel prices tend to be lower. A stay of at least 3 to 4 days is recommended to fully explore the key's notable landmarks, cultural sites, and historical attractions. While you're there, you can enjoy attractions such as the historic lighthouse, local art gallery, museums, state parks, and various recreational areas. This duration allows you to experience the rich history and vibrant culture of Summerland Key, all while keeping your trip affordable and great value for money.
  2. Look for last-minute deals on Hotels.com: To discover last-minute deals for Summerland Key, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted rates on accommodations as your travel date approaches. Consider enabling email alerts or push notifications from Hotels.com to keep informed about flash sales and special promotions, ensuring you don't miss potential savings. Additionally, the Smart ShoppingOpens in a new window tool available in the app allows you to compare hotel prices and amenities, helping you to make informed choices. If prices drop or new rooms become available, you could be among the first to know, making it easier to book a spontaneous getaway.
  3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates might help you save on your stay at a Summerland Key hotel. If you're seeking a distinctive experience, boutique hotels often provide a more personalized touch and can sometimes offer better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll recommend alternative dates that could help you secure a better deal.
  4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might want to look at hotels located in less central neighborhoods, which usually tend to be cheaper while still offering reasonable access to the sights you want to see. Additionally, exploring independent hotels a bit further out can lead to a more authentic and cost-effective experience.
  5. Become a Member: Join for free and start planning your next getaway to Summerland Key! As a member, you’ll unlock exclusive access to discounted rates on over 100,000 hotels worldwide. Enjoy benefits such as expedited booking, complimentary room upgrades when available, and special discounts on food and beverages at select VIP Access properties. Sign up today and enhance your travel experience!

Best time to go to Summerland Key

Summerland Key experiences its lowest average temperature in January, at 71.1°F (21.7°C), while August is the hottest month, with an average temperature of 84.4°F (29.1°C). September is typically the wettest month. If you’re looking to soak up the lively atmosphere in Summerland Key, March, April, and July are the peak months to visit, bustling with fellow travelers. During this peak period, the weather is mostly sunny, with little to no rainfall. However, if you prefer a more relaxed experience, May, October, and November are perfect for a quieter getaway, marked by light rainfall and mostly sunny conditions.

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