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

Summerland Key Hotel with Pool

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Check availability on Summerland Key Hotel with Pool

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Summerland Key hotels with a pool

A sunset view with a thatched structure and a palm tree by a calm body of water.
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A hotel room with a bed, a flat-screen TV, a small kitchenette, and a balcony with a view of palm trees and the ocean.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

1. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
HK$994
HK$1,374 total
includes taxes & fees
2 Nov - 3 Nov
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A waterfront building with a flat roof, large windows, and a balcony.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
HK$934
HK$1,051 total
includes taxes & fees
12 Oct - 13 Oct
Sugar Loaf Lodge
A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

3. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
HK$792
HK$891 total
includes taxes & fees
7 Oct - 8 Oct
Looe Key Reef Resort
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A balcony with a view of neighboring houses, a street, and a clear sky.
A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.
A marina with RVs docked along a waterway, surrounded by palm trees and buildings.

4. SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
HK$1,091
HK$3,286 total
includes taxes & fees
9 Oct - 10 Oct
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a swimming pool, beach area, and marina.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A waterfront property with a boat dock, a covered outdoor seating area, and a two-story building with balconies.
A covered outdoor seating area with white chairs and tables, overlooking turquoise waters and distant islands.

5. Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
HK$3,090
HK$5,875 total
includes taxes & fees
7 Oct - 8 Oct
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
A beach view with a swimming pool, palm trees, and lounge chairs.
A spacious living room with a white sofa, two armchairs, a round coffee table, and a balcony with a view of palm trees.
A two-story house with a balcony, a staircase, and a view of the beach.
A beach with palm trees, a wooden dock, and lounge chairs.

6. Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
HK$2,550
HK$5,680 total
includes taxes & fees
19 Oct - 20 Oct
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A resort with a swimming pool, beach area, and marina.
A spacious living area with a view of the ocean, a dining area with a kitchen, and a ceiling fan.
A view from a balcony overlooking a beach with a clear sky and calm sea.
A kitchen with a view of the sea, a dining table set with plates, and a blue cabinet.

7. Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
HK$3,708
HK$6,664 total
includes taxes & fees
7 Oct - 8 Oct
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
An aerial view of a resort with a large pool, palm trees, and a pier.
A balcony with wicker furniture, a view of the ocean, and a parked truck.
A spacious living area with a round wooden table, comfortable seating, and large windows offering a view of the outdoors.
A beachfront property with a covered patio, outdoor seating, and a view of the ocean.

8. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
HK$2,943
HK$5,585 total
includes taxes & fees
11 Oct - 12 Oct
Spanish Queen @Venture Out, Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A dining area with a glass table, wicker chairs, and a view of the ocean.
A resort with a swimming pool, beach area, and marina.
Outdoor dining

9. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
HK$1,772
HK$4,235 total
includes taxes & fees
7 Oct - 8 Oct
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A dining area with a wooden table set for two, white cushioned seating, and a view of the sea through a glass door.
A living room with a sofa, chairs, a coffee table, a TV, and large windows overlooking the ocean.

10. Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
HK$3,214
HK$6,534 total
includes taxes & fees
7 Oct - 8 Oct
Post Card Point #319 - Ocean Views!
View all properties

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

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Summerland Key Hotel Reviews

Looe Key Reef Resort

Looe Key Reef Resort

8/10 Good
"This is a great inexpensive place to stay. Room was clean. Resort is showing some wear but is still good. Staff are very helpful with local recommendations. There is a great gas station next door with some items for sale in case you forget something. I would stay again."
Brandy 2-night trip
Posted 12 hours ago
Looe Key Reef Resort
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Just a fantastic property, wonderful staff, great amenities, so many waterfront places to chill. Immaculate grounds with a laid back vibe, loved it!!"
Moira 1-night trip
Posted 2 days ago
Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
Richard 2-night trip
Posted 11 days ago
Sugar Loaf Lodge

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 Hotel at KOA Resort: Offers a private beach, an outdoor pool and a snack bar/deli. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool and a full-service spa. Looe Key Reef Resort: Features free self parking, an outdoor pool and complimentary wireless Internet access. 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.

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