Summerland Key Hotels with Swimming Pool

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Swimming Pools

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Summerland Key Hotels with Swimming Pools

2 outdoor pools, open 8:00 AM to 10:00 PM, pool loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1165)
"Will be staying here every single time we visit! "
United States
Rebecca
The price is RM2,512
RM3,096 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Perry Hotel & Marina Key West
3 outdoor pools, pool umbrellas, pool loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (2908)
"Room was great, the pools and beach were great"
United States
Tina
The price is RM694
RM1,083 total
includes taxes & fees
17 Dec - 18 Dec
Southernmost Beach Resort and Guesthouses
2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4.0 star property
New Town
8.0 out of 10, Very good, (1744)
"Loved staying here and would again next time we are in Key West!!"
Canada
David
The price is RM493
RM786 total
includes taxes & fees
9 Dec - 10 Dec
Blue Flamingo Resort Key West
Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
Summerland Key
8.2 out of 10, Very good, (1008)
"Tiki hit closed, wish I had known Staff very nice, rooms fine"
United States
James
The price is RM408
RM459 total
includes taxes & fees
4 Dec - 5 Dec
Sugar Loaf Lodge
Dock
Parmer's Resort

Parmer's Resort

2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1012)
"Breakfast options, a heated pool"
United States
Ricardo
The price is RM474
RM667 total
includes taxes & fees
14 Dec - 15 Dec
Parmer's Resort
Outdoor pool, pool umbrellas, pool loungers
Looe Key Reef Resort

Looe Key Reef Resort

2.5 star property
Summerland Key
7.4 out of 10, Good, (1005)
"Room was really clean and receptionist very friendly. Travelling with my son so had a nice big bed each. Balcony was nice and its only 35 mins to Key West which was oerfect"
United Kingdom
Clare
Looe Key Reef Resort
2 outdoor pools, pool loungers
Little Torch Cottages

Little Torch Cottages

2.0 star property
Summerland Key
9.2 out of 10, Wonderful, (9)
"Felt like home. We'd stay here again!"
United States
William
Little Torch Cottages
Swim-up bar
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)
"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 RM2,088
RM3,793 total
includes taxes & fees
16 Dec - 17 Dec
Atlantic View Luxury Villa with Pool
View from property
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5.0 star property
Marathon
9.2 out of 10, Wonderful, (1054)
"Rooms and property were very clean . "
United States
Jessica
The price is RM1,198
RM1,606 total
includes taxes & fees
9 Dec - 10 Dec
Isla Bella Beach Resort & Spa
2 outdoor pools, free pool cabanas, pool umbrellas
Courtyard by Marriott Faro Blanco Resort

Courtyard by Marriott Faro Blanco Resort

3.0 star property
Marathon
9.2 out of 10, Wonderful, (1000)
"Nice hotel"
United States
Ivonne
The price is RM623
RM863 total
includes taxes & fees
9 Dec - 10 Dec
Courtyard by Marriott Faro Blanco 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.
View all properties

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Awesome Experience. Such a fun Atmosphere "
Robert 4-night trip
Posted 1 day ago
Parmer's Resort

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 7 places to stay with pools. During your visit, you can explore attractions such as Upper Sugarloaf Key and Florida Keys Beaches, 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?
Parmer's Resort: Features a private beach, an outdoor pool and daily. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool and free self parking. Looe Key Reef Resort: Provides free self parking, an outdoor pool and complimentary wireless Internet access. Sugarloaf Key Hotel at KOA Resort: Features a private beach, an outdoor pool and a snack bar/deli. Little Torch Cottages: Offers sunloungers, a pool and complimentary wireless Internet access.
How many hotels with pools can I expect 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 Venture Out Keys, Coupon Bight Aquatic Preserve 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.