Summerland Key Vacation Rentals

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Check prices for these dates

Tonight
Dec 30 - Dec 31
Tomorrow
Dec 31 - Jan 1
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Summerland Key vacation rentals

Swim-up bar
Atlantic View Luxury Villa with Pool

Villa in Summerland Key

Atlantic View Luxury Villa with Pool
3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is P33,045
P60,307 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Atlantic View Luxury Villa with Pool
2 bedrooms, Internet
Starlight Serenity - Hideaway w Stunning Views

Vacation Home in Summerland Key

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
The price is P22,244
P44,679 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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.
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Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"It was so nice experience to stay there."
Tapas 1-night trip
Posted 1 day ago
Sugar Loaf Lodge

Find out more about Summerland Key

Search for holiday rentals in Summerland Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Summerland Key using one of the methods below:

  • View our selection of featured holiday rentals in Summerland Key
  • Use the map to find apartments and other holiday homes in the Summerland Key neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Summerland Key while they last

Look no further and take a look at our great range of rental properties in Summerland Key!

Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

How many vacation rentals are there in Summerland Key?

Choose from 484 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

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

What are vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.