Find Hotels with a Pool in Summerland Key, FL

  • 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 availability on Summerland Key Hotels with a Pool

Our top choices for Summerland Key hotels with a pool

Outdoor pool

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1,006 reviews)
"Clean, convenient location. "
United States
Michael
The price is AED 915
AED 1,029 total
includes taxes & fees
12 Mar - 13 Mar
Sugar Loaf Lodge
Private beach, sun loungers, beach umbrellas, beach towels

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,011 reviews)
"Staff were amazing "
United States
Thomas
The price is AED 889
AED 1,120 total
includes taxes & fees
12 Mar - 13 Mar
Parmer's Resort
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers

Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.6 out of 10, Good, (1,014 reviews)
"Staff was great everything was fine had a fun sisters trip. Great tiki bar!"
United States
Jill
Looe Key Reef Resort
Pool

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (56 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is AED 909
AED 1,671 total
includes taxes & fees
12 Mar - 13 Mar
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior

Canal front lot only. No house or RV. You need to bring your RV.

Canal front lot only. No house or RV. You need to bring your RV.
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Just as described, a place to park our RV, nice amenities, (extra 125 one time charge, but that was explained ahead of time)"
United States
Larry B.
The price is AED 547
AED 689 total
includes taxes & fees
31 Mar - 1 Apr
Canal front lot only. No house or RV. You need to bring your RV.
Pool

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (124 reviews)
"host answered our question. Did not know w& d was coin washer and dryer"
United States
Robin D.
The price is AED 826
AED 1,516 total
includes taxes & fees
20 Mar - 21 Mar
Charming cottages, dockage, pool, just minutes to Key West
Exterior

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is AED 744
AED 1,272 total
includes taxes & fees
12 Mar - 13 Mar
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Front of property

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"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 AED 2,066
AED 3,771 total
includes taxes & fees
15 Mar - 16 Mar
Atlantic View Luxury Villa with Pool
A heated pool

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is AED 826
AED 1,657 total
includes taxes & fees
12 Mar - 13 Mar
Waterfront Home
Outdoor dining

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
The price is AED 624
AED 1,092 total
includes taxes & fees
21 Mar - 22 Mar
Endless Summer Hideaway - lot 181
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

Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars

Eid al-Fitr Sale

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

Hotels with pools and hot tubs in Summerland Key

Exterior
Canal front lot only. No house or RV. You need to bring your RV.

Canal front lot only. No house or RV. You need to bring your RV.

Canal front lot only. No house or RV. You need to bring your RV.
Cudjoe Key
10.0 out of 10, Exceptional, (3)
The price is AED 547
AED 689 total
includes taxes & fees
31 Mar - 1 Apr
Canal front lot only. No house or RV. You need to bring your RV.
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

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Ocean views and warm pool!"
Juliet 1-night trip
Posted 23 hours ago
Parmer's Resort

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Summerland Key?
If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 7 places to stay with pools. During your visit, you can explore attractions like Upper Sugarloaf Key and Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that guests like for their pools.
What are some accommodations with pools in Summerland Key?
Parmer's Resort: Features a private beach, an outdoor pool, and daily. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool, and a snack bar/deli. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Provides free self parking, an outdoor pool, and complimentary wireless internet access. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Features 2 outdoor tennis courts, an outdoor pool, and free self parking. Cottage with Pool and Boat Dockage just minutes to Key West!: Offers kitchens, a communal pool, and Smart TVs.
How many hotels with pools will I be able to find in Summerland Key?
Expedia has 7 hotels in Summerland Key for your poolside break.
What is there to see and do in Summerland Key?
The picturesque setting of Upper Sugarloaf Key and Florida Keys Beaches showcase the area's natural beauty. Discover sights such as Sugarloaf Beach, Venture Key, and Venture Out Keys during your stay.
When is the best time to book a hotel with a pool in Summerland Key?
Taking into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Summerland Key is 35 inches.