Find Hotels with a Pool in Summerland Key, FL

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Top Summerland Key Hotels with a Pool

Pool
105 - Newly renovated house Oceanside and Pool

105 - Newly renovated house Oceanside and Pool

Cudjoe Key
$734 nightly
The price is $776
Nov 18 - Nov 19
Total with taxes and fees
105 - Newly renovated house Oceanside and Pool
Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1000)
"Tiki hit closed, wish I had known Staff very nice, rooms fine"
United States
James
$99 nightly
The price is $111
Nov 30 - Dec 1
Total with taxes and fees
Sugar Loaf Lodge
Dock
Parmer's Resort

Parmer's Resort

2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1005)
"Wonderful spot…loved it!!!"
Canada
Christopher
$158 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
Parmer's Resort
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
Nov 30 - Dec 1
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, a heated pool
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.6 out of 10, Exceptional, (98)
"This is a great place to stay, neighborhood is nice, very convenient with the marina and boat ramp on site. I would definitely stay here again. "
United States
Edward H.
$392 nightly
The price is $435
Nov 13 - Nov 14
Total with taxes and fees
NOV. & DEC. 50% OFF! WATERFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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, (158)
"Great location and very happy with our accommodations."
United States
Carrie B.
$286 nightly
The price is $317
Nov 13 - Nov 14
Total with taxes and fees
Cottage with Pool and 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
$170 nightly
The price is $189
Nov 13 - Nov 14
Total with taxes and fees
Canal front lot only. No house or RV. You need to bring your RV.
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
$353 nightly
The price is $392
Nov 16 - Nov 17
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath
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, (1003)
"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
$192 nightly
The price is $216
Nov 23 - Nov 24
Total with taxes and fees
Looe Key Reef Resort
Outdoor pool, a heated pool
NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

NOV. & DEC. 50% OFF! OCEANFRONT, 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
9.8 out of 10, Exceptional, (82)
"Great property, owners were very helpful and we really enjoyed our stay!"
United States
Lee J.
$472 nightly
The price is $524
Nov 16 - Nov 17
Total with taxes and fees
NOV. & DEC. 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
"Excellent service and ammenities. We enjoyed our stay, very personable resort and we took pleasure in getting to know the other patrons at the pool. The Resort is in the perfect central location, we travelled to both Islamorada and Key West a couple of days. A fishing charter picked us up right at the Resort dock. We took our catch down to Kiki's and they cooked it up for us. Also, nightly live entertainment at Kiki's just down the road. "
Tara 6-night trip
Posted 4 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 5 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches and Sugarloaf Beach, 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. Little Torch Cottages: Offers complimentary wireless internet access, a communal pool, and kitchens.
How many hotels with pools will I be able 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 Coupon Bight Aquatic Preserve 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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