Find Hotels with a Pool in Summerland Key, FL

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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

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1002)
"Great place to stary. Staff was very nice."
United States
norka
The price is ￥15,425
￥17,354 total
includes taxes & fees
Dec 19 - Dec 20
Sugar Loaf Lodge
Outdoor pool, pool umbrellas, sun 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, (1002)
"Was nice roo.s and close to my charter boat captain "
United States
Nicholas
The price is ￥19,651
￥22,108 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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, (1001)
"Room was clean and comfortable."
United States
Barbara K
The price is ￥20,894
￥28,590 total
includes taxes & fees
Dec 14 - Dec 15
Parmer's Resort
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, (50)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is ￥21,034
￥49,430 total
includes taxes & fees
Dec 14 - Dec 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Exterior
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% 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.
The price is ￥23,216
￥67,622 total
includes taxes & fees
Dec 14 - Dec 15
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
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, (120)
"Jennifer was very nice and accommodating."
United States
Randy G.
The price is ￥24,930
￥51,184 total
includes taxes & fees
Dec 15 - Dec 16
Charming cottages, dockage, pool, 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.

Canal front lot only. No house or RV. You need to bring your RV.
Cudjoe Key
The price is ￥23,216
￥29,391 total
includes taxes & fees
Dec 14 - Dec 15
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

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (88)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is ￥24,540
￥57,505 total
includes taxes & fees
Dec 15 - Dec 16
Canal front, dockage, 2 bedroom, 2 bath
Deluxe Villa, Ocean View | 4 bedrooms, laptop workspace, iron/ironing board, free WiFi
Atlantic View Luxury Villa with Pool

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 ￥78,717
￥142,978 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Atlantic View Luxury Villa with Pool
Outdoor pool, a heated pool
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% 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.
The price is ￥38,797
￥87,176 total
includes taxes & fees
Dec 14 - Dec 15
DECEMBER SAVE 60% 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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Hotels with pools and ocean views in Summerland Key

Exterior
Parmer's Resort

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1001)
The price is ￥20,894
￥28,590 total
includes taxes & fees
Dec 14 - Dec 15
Parmer's Resort
View all properties

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
The price is ￥23,216
￥29,391 total
includes taxes & fees
Dec 14 - Dec 15
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

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Great place to stary. Staff was very nice."
norka 1-night trip
Posted 6 days ago
Sugar Loaf Lodge

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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. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Offers free self parking, an outdoor pool, and complimentary wireless internet access. 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. Private Secluded Ocean View & Pool Near Key West: 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 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 Out Keys, 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.