Overseas highway in the Florida Keys taken by drone

Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

Our top choices for Summerland Key hotels with a pool

Outdoor pool

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
The price is AED 621
AED 698 total
includes taxes & fees
23 Jun - 24 Jun
Sugar Loaf Lodge
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers

Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
The price is AED 572
AED 644 total
includes taxes & fees
25 Jun - 26 Jun
Looe Key Reef Resort
Dock

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
The price is AED 658
AED 860 total
includes taxes & fees
28 Jun - 29 Jun
Parmer's Resort
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, (166 reviews)
The price is AED 512
AED 1,000 total
includes taxes & fees
22 Jun - 23 Jun
Cottage with Pool and Boat Dockage just minutes to Key West!
Pool

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (158 reviews)
The price is AED 992
AED 2,188 total
includes taxes & fees
28 Jun - 29 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
A heated pool

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
The price is AED 918
AED 1,793 total
includes taxes & fees
29 Jun - 30 Jun
Waterfront Home
Exterior detail

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
The price is AED 853
AED 2,364 total
includes taxes & fees
29 Jun - 30 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A heated pool

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
The price is AED 694
AED 2,184 total
includes taxes & fees
22 Jun - 23 Jun
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A heated pool

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very Good, (3 reviews)
The price is AED 675
AED 2,159 total
includes taxes & fees
22 Jun - 23 Jun
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Outdoor pool, a heated pool

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
The price is AED 841
AED 1,969 total
includes taxes & fees
26 Jun - 27 Jun
SAVE BIG $$ JUNE/JULY! 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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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars

Hotels with pools and hot tubs in Summerland Key

Terrace/patio
Waterfront Home

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187)
The price is AED 918
AED 1,793 total
includes taxes & fees
29 Jun - 30 Jun
Waterfront Home
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"The staff here are amazing they are so nice and helpful. The breakfast in the morning was much more than we had expected and cookies and lemonade in the afternoon was a special treat again not expected but a nice touch. Our room was somewhat dated but we’re not there to spend time in the room. My only complaint would be to please update the bed it was not comfortable at all. But I would still give this place 5 stars and recommend it to anyone. Lots of great places to eat in the area and close to places of interest."
Linda 4-night trip
Posted 1 day ago
Parmer's Resort

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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 27 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that travelers 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. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool, and a full-service spa. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool, and a snack bar/deli. Sugar Loaf Lodge: Features free self parking, an outdoor pool, and complimentary wireless internet access. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool, and free self parking.
How many hotels with pools will I be able to find in Summerland Key?
Expedia's 27 hotels in Summerland Key give you a great choice for your poolside getaway.
What is there to see and do in Summerland Key?
Explore places like Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Sugarloaf Beach.
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.