View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds

Hotels with Pool & Resorts in Summerland Key from NZ$251

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Check availability on Summerland Key Hotels with Pool

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, (1,004 reviews)
  • cleanliness
    Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
The price is NZ$251
includes taxes & fees
14 June - 15 June
Sugar Loaf Lodge
Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, pool loungers

Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
Summerland Key
7.6 out of 10, Good, (1,003 reviews)
  • cleanliness
    Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
The price is NZ$302
includes taxes & fees
2 July - 3 July
Looe Key Reef Resort
Dock

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,013 reviews)
  • cleanliness
    Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
The price is NZ$404
includes taxes & fees
23 June - 24 June
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, (165 reviews)
Cottage with Pool and Boat Dockage just minutes to Key West!
Outdoor pool, 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
Cudjoe Key
8.8 out of 10, Excellent, (97 reviews)
The price is NZ$634
includes taxes & fees
15 June - 16 June
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Outdoor pool, a heated pool

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

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
The price is NZ$739
includes taxes & fees
15 June - 16 June
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
10 outdoor pools, pool umbrellas, pool loungers

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 NZ$1,948
includes taxes & fees
14 June - 15 June
Atlantic View Luxury Villa with Pool
Outdoor pool, a heated pool

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
The price is NZ$716
includes taxes & fees
14 June - 15 June
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Outdoor pool, a heated pool

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (100 reviews)
The price is NZ$683
includes taxes & fees
12 June - 13 June
Canal front, dockage, 2 bedroom, 2 bath
A heated pool

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
The price is NZ$947
includes taxes & fees
8 July - 9 July
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 spa pools in Summerland Key

Exterior
Atlantic View Luxury Villa with Pool

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)
The price is NZ$1,948
includes taxes & fees
14 June - 15 June
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.
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Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Parmer’s Resort on Little Torch Key is the kind of place you go when you truly want to slow down and unwind—but still have everything you need within reach. The property has a classic“old Florida” charm that is not flashy or overdone—instead, it feels cozy, laid-back, and genuinely welcoming. Parmer's has that homey, relaxed vibe that makes it easy to settle in, unplug, and enjoy the simple pleasures of the Keys. It’s the perfect setting if you’re looking to escape the hustle and just breathe for a while. It’s tucked away in a quiet spot, giving you that “away-from-it-all” feeling, yet you’re still just a short drive from great food and local favorites. Places like Kiki’s, Square Grouper, and Tonio’s are all nearby, and there’s even a fun little taco spot a few miles down the road that’s worth checking out. The amenities really add to the experience without feeling overwhelming. There’s a small private beach where you can relax by the water, plus bicycles, kayaks, and stand-up paddleboards available so you can explore at your own pace. It’s easy to fill your day with outdoor activities—or do nothing at all, which is just as enjoyable here. [parmersresort.com] Another highlight is the daily breakfast, which is such a nice touch. Having that ready each morning makes the stay even more convenient. We will be back!!!"
Cheryl 3-night trip
Posted 20 hours ago
Parmer's 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 28 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 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 can I expect to find in Summerland Key?
Expedia's 28 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 Sugarloaf Beach.
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.