Summerland Key Hotel with Pool

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Check availability on Summerland Key Hotel with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Summerland Key hotels with a pool

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, (1001)
"Staff very polite and accommodating. "
United States
Gregory Mark
Looe Key Reef Resort
Dock
Parmer's Resort

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1000)
"Beautiful and relaxing "
United States
Michael
The price is HK$1,498
HK$1,939 total
includes taxes & fees
8 Jan - 9 Jan 2026
Parmer's Resort
Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1001)
"Great place to stary. Staff was very nice."
United States
norka
The price is HK$1,547
HK$1,741 total
includes taxes & fees
8 Jan - 9 Jan 2026
Sugar Loaf Lodge
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 HK$1,159
HK$1,459 total
includes taxes & fees
8 Jan - 9 Jan 2026
Canal front lot only. No house or RV. You need to bring your RV.
Outdoor pool, a heated pool
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 HK$2,325
HK$4,741 total
includes taxes & fees
10 Jan - 11 Jan 2026
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool
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, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
The price is HK$1,750
HK$2,943 total
includes taxes & fees
19 Jan - 20 Jan 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior
Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1)
The price is HK$1,322
HK$2,335 total
includes taxes & fees
29 Dec - 30 Dec
Seabreeze Escape WF RV Lot 489
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 HK$2,325
HK$4,742 total
includes taxes & fees
18 Jan - 19 Jan 2026
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Outdoor dining
Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181

Endless Summer Hideaway - lot 181
Cudjoe Key
The price is HK$1,322
HK$2,320 total
includes taxes & fees
27 Dec - 28 Dec
Endless Summer Hideaway - lot 181
Swim-up bar
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 HK$4,374
HK$7,982 total
includes taxes & fees
16 Jan - 17 Jan 2026
Atlantic View Luxury Villa with Pool
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
"Staff was wonderful. Room is sweet and on pretty piece of water. Aging property, but well kept. Quiet, clean, good shower, comfy beds. Quick trip to key west. Great deal for the money. Very happy this is where we landed."
cynthia 1-night trip
Posted 4 days ago
Sugar Loaf Lodge

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?
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. Little Torch Cottages: Offers complimentary wireless Internet access, a communal pool and kitchens.
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.

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