Hotels with Pool & Resorts in Summerland Key

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Best Summerland Key Hotels with Pool

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Frequently asked questions

What's it like visiting Summerland Key?
If taking it easy by the pool is your idea of a great getaway, you may want to look at Summerland Key, which has 5 places to stay with pools. During your visit, you can explore attractions such as Florida Keys Beaches and Sugarloaf Beach, and then relax and unwind poolside at one of the accommodation options in Summerland Key that guests like for their pools.
What are some accommodation options with pools in Summerland Key?
ISLAND PARADISE: Features complimentary wireless Internet access, a communal pool and kitchens. RV resort site/rvsite/spot/lot Cudjoe Florida mm23 Key West MONTHLY DISCOUNT 25%: Offers sunloungers, a pool and hot tubs.
How many hotels with pools can I expect to find in Summerland Key?
Expedia has 5 hotels in Summerland Key for your poolside break.
What is there to see and do in Summerland Key?
The picturesque setting of Florida Keys Beaches and Sugarloaf Beach showcase the area’s natural beauty. Discover sights such as Venture Out Keys, Upper Sugarloaf Key and Upper Sugarloaf Sound during your stay.
When is the best time to book a hotel with a pool in Summerland Key?
Taking the local weather in Summerland Key into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Summerland Key is 895 mm.