Summerland Key Hotel Guide - Hotels with Pool in Summerland Key, Florida

  • 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 Pool

Our top choices for Summerland Key hotels with a pool

Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,003 reviews)
"It was so nice experience to stay there."
United States
Tapas
The price is €192
includes taxes & fees
15 Jan - 16 Jan
Sugar Loaf Lodge
A heated 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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (54 reviews)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is €347
includes taxes & fees
15 Jan - 16 Jan
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, pool umbrellas, pool loungers
Looe Key Reef Resort

Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.4 out of 10, Good, (1,005 reviews)
"Clean old Florida motel. For the price we would stay again."
United States
James
Looe Key Reef Resort
Private beach, sun-loungers, beach umbrellas, beach towels
Parmer's Resort

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,002 reviews)
"Gorgeous view, convenient location, friendly staff! "
United States
Sandra
The price is €248
includes taxes & fees
19 Jan - 20 Jan
Parmer's Resort
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
The price is €166
includes taxes & fees
19 Jan - 20 Jan
Canal front lot only. No house or RV. You need to bring your RV.
Pool
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (155 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
The price is €279
includes taxes & fees
15 Jan - 16 Jan
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool
Charming cottages, dockage, pool, just minutes to Key West

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, (121 reviews)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
United States
ANJANA
The price is €328
includes taxes & fees
15 Jan - 16 Jan
Charming cottages, dockage, pool, just minutes to Key West
A heated pool
Waterfront Home

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (175 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is €349
includes taxes & fees
19 Jan - 20 Jan
Waterfront Home
Exterior
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
A heated pool
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
2.5 star property
Cudjoe Key
9.2 out of 10, Wonderful, (7 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is €531
includes taxes & fees
19 Jan - 20 Jan
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"Staff was friendly. Room was clean. Furniture a little worn but bed comfortable and clean linens "
Lora 2-night trip
Posted 5 days ago
Looe Key Reef 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 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?
Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Features free self parking, an outdoor pool and complimentary wireless Internet access. Parmer's Resort: Offers a private beach, an outdoor pool and daily. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Provides 2 outdoor tennis courts, an outdoor pool and free self parking. Sugarloaf Key Hotel at KOA Resort: Features a private beach, an outdoor pool and a snack bar/deli. Little Torch Cottages: Hotel located near Florida Keys Beaches. Offers a sauna, 2 outdoor swimming pools and free self parking.
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 Florida Keys Beaches and Sugarloaf Beach showcase the area's natural beauty. Discover sights such as Venture Out Keys, Upper Sugarloaf Key and Coupon Bight Aquatic Preserve 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.