Summerland Key, FL

Travel Guide

Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house

Where to stay in Summerland Key

Default Image

Cutthroat Harbor Estates

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

Cutthroat Harbor Estates
Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

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

Sugarloaf Shores
Default Image

Bay Point

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

Bay Point
Default Image

Cudjoe Gardens

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

Cudjoe Gardens
Default Image

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Venture Out Keys and Cook Island are some notable places to visit nearby.

Breezeswept Beach Estates
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
The price is ￥16,258 per night from Oct 16 to Oct 17
￥16,258
￥23,245 total
Oct 16 - Oct 17
includes taxes & 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 ...
9/10 Wonderful! (1,002 reviews)
"Excellent laid back property. Close to a good restaurant"

Reviewed on Oct 9, 2025

Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
The price is ￥18,065 per night from Oct 16 to Oct 17
￥18,065
￥20,324 total
Oct 16 - Oct 17
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,000 reviews)
"This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!"

Reviewed on Oct 6, 2025

Sugar Loaf Lodge
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 3-star 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 ...
9.6/10 Exceptional! (439 reviews)
"It was great!"

Reviewed on Oct 7, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 621 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.
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
9.4/10 Exceptional! (82 reviews)
"Nice house in a great location."

Reviewed on Sep 29, 2025

Old Florida Style, wrap around porch, boat basin for dockage, open water
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and tennis courts. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (229 reviews)
"This is by far the best property we have rented in Venture Out. Everything was amazing, everything was well thought out, super clean, and the extra little thoughtful touches went a long way! We really enjoyed the complimentary pie and the book was very well put together and helpful!"

Reviewed on Aug 15, 2025

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Florida Keys Beaches and Venture ...
9.6/10 Exceptional! (34 reviews)
"This home was a 10/10 experience. Everything was top notch from the cleanliness to the amenities available. It looks exactly like the pictures online but in person it was so much better. The view from the balcony was the best part about it as well as the boat access. We also spent lots of time at ..."

Reviewed on Sep 28, 2025

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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.

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

Sugarloaf Beach

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

Sugarloaf Beach

Upper Sugarloaf Key

4/5(21 reviews)

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

Upper Sugarloaf Key

Crab Key

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

Crab Key

Squirrel Key

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

Squirrel Key

Pye Key

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

Pye Key

Things to do

Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

￥11,711
per traveler
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Family navigating the sea on the glass bottom boat in Key West

Key West Sunset Cruise & Glass Bottom Eco Tour

￥9,422
per adult
74% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

￥8,144
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
We never take more than 6 people on-board to let you ENJOY your adventure!

Dolphin & Snorkel

￥19,775
per adult
Dolphin & Snorkel
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

￥6,606
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West Haunted Tour : Ghosts & Gravestones

Key West Haunted Tour : Ghosts & Gravestones

￥5,837
per adult
86% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
See all activities in Summerland Key

Cities near Summerland Key

South Beach featuring tropical scenes, general coastal views and a beach

Key West

Big Pine Key featuring a river or creek, a bay or harbor and general coastal views

Big Pine Key