A coastal road with a beach on one side and a marina with boats on the other.

Summerland Key Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Summerland Key holiday rentals

2 bedrooms, Internet

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is S$924
includes taxes & fees
7 Jul - 8 Jul
Starlight Serenity - Hideaway w Stunning Views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Very well maintained and clean. Pool area is very nice and margaritas from the bar are great."
Gilian 2-night trip
Posted 3 hours ago
Sugarloaf Key Hotel at KOA Resort

Frequently asked questions

Can I find holiday rentals in Summerland Key?

Yes, there are holiday rentals close to the most popular sights in Summerland Key, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Summerland Key has to offer?

Sugarloaf Key RV Resort & Cottages: This highly rated holiday home rental in Summerland Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Summerland Key?

Choose from 473 Expedia holiday rentals in Summerland Key for a memorable holiday.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Sugarloaf Beach and Crab Key are other places to visit while you're in town.

What are holiday rentals like in Summerland Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Summerland Key. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.