Summerland Key Hotel Guide - Hotels with Pool in Summerland Key, Florida

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Check availability on Summerland Key Hotels with Pool

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Summerland Key Hotels with Pool

Dock
Parmer's Resort

Parmer's Resort

2.5 star property
Summerland Key
  • Outdoor pool
  • Pool loungers
  • On private beach
9.0 out of 10, Wonderful, (1008)
Floating in the refreshing outdoor pool surrounded by swaying palms creates the perfect complement to days spent exploring the private beach. This waterfront haven offers kayaking, sailing, and boat tours just steps from comfortable, individually furnished rooms.
The price is €133
includes taxes & fees
30 Nov - 1 Dec
Parmer's Resort
Outdoor pool
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 star property
Summerland Key
  • Outdoor pool
8.2 out of 10, Very good, (1005)
Splash into serenity at the heated outdoor pool overlooking beautiful ocean vistas. This hotel balances aquatic bliss with active pursuits, offering tennis courts, marina access, kayaking, and boat tours, all amid peaceful surroundings praised by guests.
The price is €96
includes taxes & fees
3 Dec - 4 Dec
Sugar Loaf Lodge
Exterior
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
  • Near the beach
8.2 out of 10, Very good, (48)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pool
Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
  • Air conditioning
9.2 out of 10, Wonderful, (160)
The price is €280
includes taxes & fees
6 Dec - 7 Dec
Cottage with Pool and Dockage, just minutes to Key West
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
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
  • Air conditioning
8.6 out of 10, Excellent, (151)
The price is €224
includes taxes & fees
15 Dec - 16 Dec
Cottage with Pool and Boat Dockage just minutes to Key West!
Outdoor pool, pool umbrellas, pool loungers
Looe Key Reef Resort

Looe Key Reef Resort

2.5 star property
Summerland Key
  • Outdoor pool
  • Pool loungers
  • Near the beach
7.4 out of 10, Good, (1004)
Sparkling outdoor pool creates the perfect retreat after adventures exploring Looe Key Reef. Surrounded by sun loungers and umbrellas, swimmers can enjoy poolside dining or venture into scuba diving, kayaking, and sailing directly from the dock.
Looe Key Reef Resort
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.

Cudjoe Key
  • Outdoor pool
  • Hot tub
The price is €166
includes taxes & fees
29 Nov - 30 Nov
Canal front lot only. No house or RV. You need to bring your RV.
Outdoor pool, a heated pool
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key
  • Outdoor pool
  • Children's pool
  • Hot tub
9.6 out of 10, Exceptional, (100)
The price is €405
includes taxes & fees
1 Dec - 2 Dec
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key
  • Outdoor pool
  • Near the beach
9.8 out of 10, Exceptional, (82)
The price is €494
includes taxes & fees
3 Dec - 4 Dec
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Pool
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates
  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
  • Air conditioning
8.4 out of 10, Very good, (118)
The price is €477
includes taxes & fees
7 Dec - 8 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming 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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views. "
Heather 1-night trip
Posted 4 days ago
Parmer's Resort

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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 Upper Sugarloaf Key and Florida Keys Beaches, 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. Sugar Loaf Lodge: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool and free self parking. Looe Key Reef Resort: Provides free self parking, an outdoor pool and complimentary wireless Internet access. Sugarloaf Key Hotel at KOA Resort: Features a private beach, an outdoor pool and a snack bar/deli. Old Florida Style, wrap around porch, boat basin for dockage, open water: Features kitchens, a communal pool and televisions.
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 Upper Sugarloaf Key and Florida Keys Beaches showcase the area's natural beauty. Discover sights such as Venture Out Keys, Coupon Bight Aquatic Preserve and Upper Sugarloaf Sound 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.