Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

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Dec 2 - Dec 3
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Dec 3 - Dec 4
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Dec 5 - Dec 7
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Dec 12 - Dec 14

Top Summerland Key Hotels with a Pool

Dock
Parmer's Resort

Parmer's Resort

2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1011)
"Breakfast options, a heated pool"
United States
Ricardo
$144 nightly
The price is $162
Dec 14 - Dec 15
Total with taxes and fees
Parmer's Resort
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
$99 nightly
The price is $111
Dec 3 - Dec 4
Total with taxes and fees
Sugar Loaf Lodge
Exterior
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, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
$286 nightly
The price is $317
Dec 3 - Dec 4
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pool
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$285 nightly
The price is $316
Dec 6 - Dec 7
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West
Outdoor pool, a heated pool
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$391 nightly
The price is $434
Dec 3 - Dec 4
Total with taxes and fees
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Pool
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, (151)
"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.
$228 nightly
The price is $253
Dec 15 - Dec 16
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to 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
$169 nightly
The price is $188
Dec 3 - Dec 4
Total with taxes and fees
Canal front lot only. No house or RV. You need to bring your RV.
Outdoor pool, pool umbrellas, sun 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
$164 nightly
The price is $184
Dec 8 - Dec 9
Total with taxes and fees
Looe Key Reef Resort
Outdoor dining
Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181

Cudjoe Key
$198 nightly
The price is $211
Dec 3 - Dec 4
Total with taxes and fees
Endless Summer Hideaway - lot 181
Outdoor pool, a heated pool
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$504 nightly
The price is $560
Dec 3 - Dec 4
Total with taxes and fees
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views. "
Heather 1-night trip
Posted 8 days ago
Parmer's Resort

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. 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. Private Secluded Ocean View & Pool Near Key West: Offers sun loungers, a pool, and complimentary wireless internet access.
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 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 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.

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