Summerland Key

Travel Guide

View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds
View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds
Aerial view of overseas highway and bridge road surrounded by blue water and the Gulf of Mexico, Summerland Key, United States.
Aerial view of road and bridge over turquoise water along the coastline, Summerland Key, Florida, United States.
Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.

Where to stay in Summerland Key

Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.

Sugarloaf Shores
Bird refuge wildlife background panorama banner of nature landscape ocean birds in Key West, Florida. Animals of the USA.

Cutthroat Harbor Estates

While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Venture Key.

Cutthroat Harbor Estates
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Cudjoe Gardens

While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Upper Sugarloaf Sound.

Cudjoe Gardens
Bahia Honda State Park - Calusa Beach, Florida Keys - tropical beach - USA.

Breezeswept Beach Estates

While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Big Pine Key Flea Market.

Breezeswept Beach Estates
Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the bar and the helpful staff in their reviews. ...
7.6/10 Good! (1,015 reviews)
The whole building was so old it was literally crumbling and felt unsafe. The door to our room was so ill fitting and had been broken into so many times it barely locked and you could see day light coming through all around the edges.

Reviewed on 24 Feb, 2026

Looe Key Reef Resort
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
The price is S$476 per night from 5 Mar to 6 Mar
S$476
5 Mar - 6 Mar
includes taxes & fees
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
9/10 Wonderful! (1,015 reviews)
What a wonderful place to stay. Very beautiful and tranquil. If you are looking for things to do, it is there. Everyone there was extremely helpful and was quick to go out of their way to make sure your stay was enjoyable.

Reviewed on 24 Feb, 2026

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 Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9.8/10 Exceptional! (492 reviews)
Very clean and great staff. Perfect location for access to all the islands. Had the corner unit, very large and spacious. Would definitely go back!!!

Reviewed on 21 Feb, 2026

Sugarloaf Key Hotel at KOA Resort
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.
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Stay at this family-friendly hotel in Orlando. Enjoy free Wi-Fi, 6 outdoor pools and 3 restaurants. Our guests praise the pool and the helpful staff in their ...
9.2/10 Wonderful! (4,693 reviews)
Room was very clean upon arrival, having access to so many pools was definitely the highlight. You can tell everything is very well maintained. The market place is a nice a little bonus as well if you forgot something or looking to grab something quick. Walking to get coffee from the market place ...

Reviewed on 24 Feb, 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
Vacation Village Orlando, Celebration

Vacation Village Orlando, Celebration

3 out of 5
2975 Arabian Nights Blvd Kissimmee FL
Stay at this family-friendly condo in Kissimmee. Enjoy free Wi-Fi, 7 outdoor pools and 7 hot tubs. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (3,461 reviews)
Staff, amenities, location, cleanliness

Reviewed on 23 Feb, 2026

Vacation Village Orlando, Celebration
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Stay at this spa hotel in Orlando. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
9/10 Wonderful! (3,931 reviews)
Our 2 bedroom villa was absolutely amazing and very clean and comfortable and I truly love staying there! We were only there for a one night stay, but I really love the property and would highly recommend it to others. We don’t golf but if we did, it would be an excellent choice for people as the ...

Reviewed on 24 Feb, 2026

Marriott's Grande Vista
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

Things to do