Summerland Key, FL

Travel Guide

A coastal road with a beach on one side and a marina with boats on the other.
A coastal pier extending into the sea, surrounded by rocky shores and greenery.
An aerial view of a long bridge over turquoise waters with clear visibility of the bridge's structure and vehicles.
An aerial view of a long bridge over turquoise waters with clear visibility of the bridge's structure and surrounding landscape.
A long bridge over turquoise waters with clear skies.

Where to stay in Summerland Key

Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about Summerland Key
Learn more about Summerland Key
An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

Bay Point might not have many top sights, but Lower Sugarloaf Sound and Florida Keys Beaches are two attractions nearby that you can check out.

A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.

A waterfront property with a pool, palm trees, and a building with a white roof.

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

An aerial view of a bridge over turquoise water.

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Big Pine Key Flea Market are some notable places to visit nearby.

Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
$198 nightly
The price is $223 total per night from Nov 30 to Dec 1
$223 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Get rates
Sugarloaf Key Hotel at KOA Resort
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
$161 nightly
The price is $181 total per night from Nov 9 to Nov 10
$181 total
Nov 9 - Nov 10
Total with taxes and fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Looe Key Reef Resort
See all 646 properties in Summerland 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.
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

3 out of 5
311 Johnson Rd Summerland Key FL
Stay at this vacation home in Summerland Key. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
9.2/10 Wonderful! (41 reviews)
"Clean and quiet bungalow that is convenient to Key West but far enough away to enjoy the quiet."

Reviewed on Nov 4, 2026

Sugarloaf Key RV Resort & Cottages
Keys Beach houses with a daily, rental license. Just remodeled

Keys Beach houses with a daily, rental license. Just remodeled

Summerland Key FL
Book a stay at this beach vacation home in Summerland Key. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Crab Key and Pye Key are located ...
Keys Beach houses with a daily, rental license. Just remodeled
Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,

Little Torch Key FL
Stay at this cottage in Summerland Key. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Boondocks Grille & Draft House and Big Pine Key ...
8.4/10 Very Good! (210 reviews)
"This entire home should be condemned We left Wouldn’t stay the night We were forced to change for a wedding came back and checked into a decent place The ac non existent in 1/2 the house Windows with cardboard and duct tape Place was absolute trash Apparently zero standard to be in VRBO"

Reviewed on Oct 18, 2026

Direct Oceanfront Cottage-Sunrise View- #2,
See all properties in Summerland 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.

Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

Things to do

12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

$33
per adult
82% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

$39
per adult
88% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

$70
per adult
76% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
Key West's Island Eco Tour: Kayaking, Snorkeling & Sandbar Adventure

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

$130
per adult
98% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

$33
per adult
Full Day Trip in Key West from Miami
See all activities in Summerland Key

Frequently asked questions

Is Summerland Key worth visiting?
Summerland Key is worth visiting for its local dining scene, where travelers can enjoy fresh seafood and Italian cuisine, including delicious pasta. The area also offers opportunities to explore nearby places like Little Torch Key and Sugarloaf Key.
When is the best time to visit Summerland Key?
The best time to visit Summerland Key is from November through March, when the weather is typically mild and pleasant. For fewer crowds and better value, the quieter, warmer months of June through September are a good option, offering a more relaxed experience.
What is Summerland Key known for?
Summerland Key is known for its unique island environment, serving as a gateway to nearby Little Torch Key, Sugarloaf Key, and Cudjoe Key. Travelers can explore these distinct keys, each offering a relaxed atmosphere and a chance to experience the area's natural beauty.
What is a good itinerary length for Summerland Key?
A good itinerary length for Summerland Key is two to three days to explore nearby Little Torch Key and Sugarloaf Key, and enjoy a Guided Clear Kayak Eco-Tour. For an extended stay of four to five days, travelers can also visit Cudjoe Key, experience a Marathon Backcountry Fishing Charter, and savor the local seafood. See Summerland Key Activities.
How do I plan a trip to Summerland Key?
To plan your trip to Summerland Key, book flights and places to stay on Expedia in advance. Consider a rental car to explore nearby nature areas like Little Torch Key and Sugarloaf Key. Plan activities such as a Guided Clear Kayak Eco-Tour or a Marathon Backcountry Fishing Charter for early morning or late afternoon.
What cuisines can you find in Summerland Key?
In Summerland Key, you can find Caribbean cuisine, with dishes like jerk chicken, rice and peas, and plantains. Travelers also enjoy fresh seafood options. Additionally, there are Italian choices such as pasta and pizza, and Latin American flavors like tacos and empanadas.
Can I book a refundable hotel in Summerland Key?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Summerland Key by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Summerland Key with Expedia?
Expedia makes it easier to plan your Summerland Key trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Summerland Key?
The best choice depends on your travel style. Hotels in Summerland Key can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Summerland Key trip on Expedia?
Once you've booked your Summerland Key trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Summerland Key trip?
Expedia offers customer support before, during, and after your Summerland Key trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Summerland Key?
If it's your first trip to Summerland Key, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Summerland Key hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Summerland Key hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Summerland Key

A beach with palm trees, people sunbathing, and a resort in the background.

Key West

A calm river with boats, lush greenery, and a clear blue sky.

Big Pine Key

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