Hotels in Summerland Key

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Tonight
Aug 23 - Aug 24
Tomorrow
Aug 24 - Aug 25
Next weekend
Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

Top 5 hotels in Summerland Key at a glance

  1. Parmer's Resort — 2.5-star hotel in Summerland Key. Guest rating: 9.0/10 — Wonderful.
  2. Looe Key Reef Resort — 2.5-star hotel in Summerland Key. Guest rating: 7.6/10 — Good.
  3. Sugar Loaf Lodge — 2.5-star hotel in Summerland Key. Guest rating: 8.2/10 — Very Good.
  4. Starlight Serenity - Hideaway w Stunning Views — 2-star hotel in Summerland Key. Guest rating: 10/10 — Exceptional.
  5. Atlantic View Luxury Villa with Pool — 3.5-star hotel in Summerland Key. Guest rating: 7.4/10 — Good.

Where to stay in Summerland Key?

Parmer's Resort

Parmer's Resort
Summerland Key
$119
$167 total
includes taxes & fees
Aug 24 - Aug 25
Parmer's Resort

Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
$101
$114 total
includes taxes & fees
Sep 2 - Sep 3
Looe Key Reef Resort

Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
$119
$134 total
includes taxes & fees
Aug 24 - Aug 25
Sugar Loaf Lodge

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
$229
$604 total
includes taxes & fees
Aug 25 - Aug 26
Starlight Serenity - Hideaway w Stunning Views

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
$575
$1,041 total
includes taxes & fees
Sep 9 - Sep 10
Atlantic View Luxury Villa with Pool

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
$118
$133 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn Key West FL

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
$114
$188 total
includes taxes & fees
Sep 7 - Sep 8
Hilton Key West Resort & Marina

Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
$209
$298 total
includes taxes & fees
Aug 24 - Aug 25
Margaritaville Beach House Key West

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
Punta Brisa
$100
$253 total
includes taxes & fees
Sep 1 - Sep 2
Old Wooden Bridge Resort and Marina

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
Marathon
$135
$191 total
includes taxes & fees
Sep 1 - Sep 2
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Knight's Key Suites

Knight's Key Suites
Marathon
$69
$99 total
includes taxes & fees
Sep 3 - Sep 4
Knight's Key Suites

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
Marathon
$226
$314 total
includes taxes & fees
Sep 22 - Sep 23
Isla Bella Beach Resort & Spa

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton
Marathon
$147
$203 total
includes taxes & fees
Sep 7 - Sep 8
Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Captain Pips Marina & Hideaway

Captain Pips Marina & Hideaway
Marathon
$99
$140 total
includes taxes & fees
Sep 1 - Sep 2
Captain Pips Marina & Hideaway

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
Marathon
$133
$177 total
includes taxes & fees
Sep 15 - Sep 16
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West
Key West
$222
$295 total
includes taxes & fees
Sep 19 - Sep 20
Hyatt Vacation Club at Beach House, Key West

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
$107
$153 total
includes taxes & fees
Aug 24 - Aug 25
Ibis Bay Beach Resort

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
$200
$271 total
includes taxes & fees
Aug 31 - Sep 1
Hyatt Vacation Club at Windward Pointe, Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
$116
$187 total
includes taxes & fees
Aug 24 - Aug 25
Blue Flamingo Resort Key West

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
$169
$190 total
includes taxes & fees
Aug 24 - Aug 25
Courtyard by Marriott Key West Waterfront
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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 August
Typical weather for Summerland Key
August
High 30°C / low 28°C. Sunny most days.
View properties in August
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Monthly weather averages (˚C)

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.

Top landmarks in Summerland Key

Sugarloaf Beach

8.4/10 (38 reviews)
Whether you want to collect beach glass or watch the sunset, Sugarloaf Beach is a spot you might want to check out, located 8.1 mi (13 km) from central Summerland Key. Catch the sunset by the shore at Florida Keys Beaches, just a short walk away.
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Upper Sugarloaf Key

8.6/10 (54 reviews)
Upper Sugarloaf Key is 5.2 mi (8.3 km) from central Summerland Key, why not stop by during your stay.
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Pye Key

Pye Key is 1.9 mi (3 km) from central Summerland Key, why not stop by during your stay.
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Upper Sugarloaf Sound

9.2/10 (17 reviews)
Listen to the relaxing sound of the water and take some great vacation pics at Upper Sugarloaf Sound located 6.3 mi (10.2 km) from central Summerland Key.
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Venture Key

Venture Key is 1.7 mi (2.8 km) from central Summerland Key, why not stop by during your stay.
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Crab Key

Crab Key is 1.4 mi (2.3 km) from central Summerland Key, why not stop by during your stay.
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Squirrel Key

Squirrel Key is 11.3 mi (18.1 km) from central Summerland Key, why not stop by during your stay.
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Boondocks Grille & Draft House

You could stop off for a few afternoon drinks at Boondocks Grille & Draft House when visiting Summerland Key.
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Learn more about Summerland Key

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

See all hotels in Summerland Key
A long bridge over turquoise waters with clear skies.

Check out reviews of Summerland Key hotels guests love

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Very clean. Great sunrise view. Staff are super nice. Good coffee!"
Amy 1-night trip
Posted 4 days ago
Parmer's Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"We had an amazing stay AGAIN at Sugarloaf RV & Cottage Resort in the Florida Keys! The property was beautiful, peaceful, clean, and the perfect place to relax and enjoy the Keys. The location is fantastic—close enough to Key West while still giving you that quiet, laid-back island feeling. The staff was friendly and welcoming, and everything was well maintained. We especially loved the tropical atmosphere and being able to truly disconnect and enjoy paradise. 🌴☀️🌊 We’ll definitely be back and highly recommend Sugarloaf to anyone looking for a relaxing Florida Keys getaway!"
Osmany 3-night trip
Posted 5 days ago
Sugarloaf Key RV Resort & Cottages
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Excellent place to Stay. calm and relaxed environment"
Ashish 1-night trip
Posted 6 days ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Great clean place to stay with a great tiki bar/restaurant/pool and fabulous dive/snorkle center on site with a fabulous crew that takes you to the protected Looe Key Reef. Highly recommend the water trip over anything in Key West,"
Bonita 4-night trip
Posted 7 days ago
Looe Key Reef Resort

Frequently asked questions

What accommodations do travelers like in Summerland Key?
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 476 vacation homes. You can also consider one of 8 villas or 48 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.

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