A coastal road with a beach on one side and a marina with boats on the other.

Search Hotels with Pool in Summerland Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Summerland Key Hotels with Pool

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Summerland Key hotels with a pool

Dock

1. Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
The price is ฿3,660
฿5,207 total
includes taxes & fees
10 Aug - 11 Aug
Parmer's Resort
Outdoor pool

2. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
The price is ฿3,972
฿4,469 total
includes taxes & fees
26 Aug - 27 Aug
Sugar Loaf Lodge
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

3. 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 snorkelling adventures nearby.
The price is ฿4,681
฿5,266 total
includes taxes & fees
26 Aug - 27 Aug
Looe Key Reef Resort
Outdoor pool, pool umbrellas, pool loungers

4. Hampton Inn Key West FL

Hampton Inn Key West FL
2.5 star property
Key West
9.0 out of 10, Wonderful, (1,442 reviews)
  • cleanliness
    Splash into ocean-view paradise at this poolside haven with loungers, umbrellas, and refreshing cocktail service.
The price is ฿4,937
฿5,554 total
includes taxes & fees
30 Aug - 31 Aug
Hampton Inn Key West FL
6 outdoor pools, free pool cabanas, pool umbrellas

5. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
4.0 star property
Stock Island
9.0 out of 10, Wonderful, (1,837 reviews)
  • cleanliness
    Float above the Florida Keys in a waterfront paradise with 6 serene pools, a private marina, and breathtaking sunset views.
The price is ฿4,085
฿6,595 total
includes taxes & fees
18 Aug - 19 Aug
Hilton Key West Resort & Marina
Food and drink

6. Margaritaville Beach House Key West

Margaritaville Beach House Key West
4.0 star property
Key West
8.8 out of 10, Excellent, (1,793 reviews)
  • cleanliness
    Float in serene waters at this sun-soaked poolside paradise with direct beach access and friendly round-the-clock service.
The price is ฿6,574
฿9,507 total
includes taxes & fees
27 Aug - 28 Aug
Margaritaville Beach House Key West
10 outdoor pools, pool umbrellas, pool loungers

7. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
  • cleanliness
    Private plunge pool paradise unfolds with Atlantic views and 7 outdoor oases for sun-drenched days.
The price is ฿21,885
฿37,827 total
includes taxes & fees
11 Aug - 12 Aug
Atlantic View Luxury Villa with Pool
2 outdoor pools, pool cabanas (surcharge), pool umbrellas

8. Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into paradise at this waterfront hotel offering 2 outdoor pools, a hot tub, and free cabanas for a tranquil Florida escape.
The price is ฿5,040
฿6,984 total
includes taxes & fees
27 Aug - 28 Aug
Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys
On the beach, sun-loungers, beach umbrellas, beach towels

9. Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa
5.0 star property
Marathon
9.2 out of 10, Wonderful, (1,206 reviews)
  • cleanliness
    Sun-kissed island retreat offers five heated pools with loungers and poolside cocktails.
The price is ฿7,360
฿10,293 total
includes taxes & fees
27 Aug - 28 Aug
Isla Bella Beach Resort & Spa
Outdoor pool, open 8:30 AM to 8:00 PM, pool loungers

10. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (360 reviews)
  • cleanliness
    Soak in tropical views at the outdoor pool, then paddle away from this waterfront cottage with an on-site marina and private dock.
The price is ฿3,248
฿8,348 total
includes taxes & fees
11 Aug - 12 Aug
Old Wooden Bridge Resort and Marina
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

Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars

Top Summerland Key Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"A clean comfortable room, with a lovely view from the back patio! All staff were very helpful."
Marjorie 1-night trip
Posted 3 days ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"Very "Florida Keys" type of place to stay. The good: Very convenient, super friendly staff, big pool, the overall "Keys" vibe. Rooms were decent and clean. Dive and snorkeling trips daily and a very convenient Shell station next door. The not so great: Rooms a bit dated and in need of some minor repairs here and there. The Tiki Hut ran out of food for a couple of days so we had to search out other places to eat in the evenings. Nothing was bad enough for us to not want to go back! Outstanding staff!"
Mark 10-night trip
Posted 1 month ago
Looe Key Reef Resort

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 27 places to stay with pools. During your visit, you can explore attractions such as Florida Keys Beaches, and then relax and unwind poolside at one of the accommodation options in Summerland Key that travellers 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. Sugarloaf Key RV Resort & Cottages: Offers a private beach, an outdoor pool and a full-service spa. Sugarloaf Key Hotel at KOA Resort: Provides free self parking, an outdoor pool and complimentary wireless Internet access. Looe Key Reef Resort: Features a private beach, an outdoor pool and a snack bar/deli. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Offers free self parking, an outdoor pool and complimentary wireless Internet access.
How many hotels with pools can I expect 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 such as Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Venture Out Keys.
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.