Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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 ￥26,915
￥30,280 total
includes taxes & fees
Jun 22 - Jun 23
Sugar Loaf Lodge
Private beach, sun loungers, beach umbrellas, beach towels

Parmer's Resort

Parmer's Resort
2.5 star property
Summerland Key
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
The price is ￥28,568
￥37,344 total
includes taxes & fees
Jun 8 - Jun 9
Parmer's Resort
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, (1,001 reviews)
  • cleanliness
    Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
The price is ￥26,163
￥29,433 total
includes taxes & fees
Jun 7 - Jun 8
Looe Key Reef Resort
Exterior

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, (172 reviews)
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Exterior

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (170 reviews)
The price is ￥28,667
￥56,538 total
includes taxes & fees
Jun 3 - Jun 4
Cottage with Pool and Dockage, just minutes to Key West
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 ￥28,712
￥66,396 total
includes taxes & fees
Jun 2 - Jun 3
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, (99 reviews)
The price is ￥32,250
￥67,317 total
includes taxes & fees
Jun 4 - Jun 5
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 ￥28,428
￥92,662 total
includes taxes & fees
Jun 9 - Jun 10
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Outdoor pool, a heated pool

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

SAVE BIG $$$ JUNE!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (90 reviews)
The price is ￥36,471
￥85,682 total
includes taxes & fees
Jun 9 - Jun 10
SAVE BIG $$$ JUNE!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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 ￥36,464
￥101,855 total
includes taxes & fees
Jun 1 - Jun 2
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
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

Top Summerland Key Hotel Reviews

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

10/10 Excellent
"The property and Venture Out community were as described and very well maintained. The check in process was smooth and the whole experience is turn key. The house itself was very clean with several extras supplied, including linens, towels, and daily use kitchen items, in addition to Kayaks and bicycles. Highly recommend this home and the community as a base camp if you’re looking for a peaceful setting with an easy commute to Key West or the middle keys"
Mohammad H. 7-night trip
Posted 2 days ago
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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 25 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. Sugar Loaf Lodge: Provides a private beach, an outdoor pool, and a snack bar/deli. Sugarloaf Key RV Resort & Cottages: Hotel located near Florida Keys Beaches. Features 2 outdoor tennis courts, an outdoor pool, and free self parking. Looe Key Reef Resort: Offers free self parking, an outdoor pool, and complimentary wireless internet access.
How many hotels with pools will I be able to find in Summerland Key?
Expedia's 25 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.