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
26 Sept - 27 Sept
Tomorrow
27 Sept - 28 Sept
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Our top choices for Summerland Key hotels with a pool

A swimming pool with blue and white tiles, surrounded by lounge chairs and palm trees.
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.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

1. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkelling adventures nearby.
HK$594
HK$668 total
includes taxes & fees
27 Sept - 28 Sept
Looe Key Reef Resort
A sunset view with a thatched structure and a palm tree by a calm body of water.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
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.

2. 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$1,127
HK$1,523 total
includes taxes & fees
5 Oct - 6 Oct
Parmer's Resort
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A waterfront building with a flat roof, large windows, and a balcony.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
HK$777
HK$874 total
includes taxes & fees
27 Sept - 28 Sept
Sugar Loaf Lodge
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, a marina, and a flag.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

4. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
HK$980
HK$3,076 total
includes taxes & fees
2 Oct - 3 Oct
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.
A waterfront property with a two-story building, a covered outdoor area, and a dock.
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.

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
HK$1,012
HK$3,040 total
includes taxes & fees
29 Sept - 30 Sept
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A marina with boats, a dock, and a white building with a balcony.
A covered balcony with a table and chairs, a grill, and a boat docked nearby.
A waterfront property with a covered porch, a boat dock, and a clear sky.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

6. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
HK$1,169
HK$3,208 total
includes taxes & fees
28 Sept - 29 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.
A waterfront property with a view of the sea, a dock, and a building with balconies.
A waterfront property with a pool, multiple houses, and a boat dock.
A marina with bicycles parked near the water, a boat docked, and a building with a balcony.

7. Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
HK$1,941
HK$3,799 total
includes taxes & fees
28 Sept - 29 Sept
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

8. 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
HK$1,235
HK$3,379 total
includes taxes & fees
28 Sept - 29 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A living room with a television displaying a show, a ceiling fan, and a window with blinds.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

9. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
HK$1,412
HK$4,273 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A covered outdoor area with wicker furniture and string lights.

10. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
HK$1,359
HK$3,533 total
includes taxes & fees
28 Sept - 29 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
Hot tub
5 stars
Spa

Hotels with pools and hot tubs in Summerland Key

A waterfront property with a covered porch, a boat dock, and a clear sky.
A bedroom with a bed, a ceiling fan, a window with blinds, and a door with a sign.
A marina with boats, a dock, and a white building with a balcony.
A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
HK$1,169
HK$3,208 total
includes taxes & fees
28 Sept - 29 Sept
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.
A living room with a television displaying a show, a ceiling fan, and a window with blinds.
A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.
A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
HK$1,412
HK$4,273 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A kitchen with white cabinets, a stove, and a dining area with chairs and a table.

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
HK$1,235
HK$3,379 total
includes taxes & fees
28 Sept - 29 Sept
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 waterfront property with a pool, a covered outdoor area, and a mobile home labeled 'Premier.'
A coastal residential area with houses, a marina, and a flag.

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
HK$1,647
HK$3,897 total
includes taxes & fees
28 Sept - 29 Sept
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A covered outdoor area with a glass table and chairs, overlooking a body of water and a distant island.

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
HK$1,729
HK$3,974 total
includes taxes & fees
2 Oct - 3 Oct
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
A coastal residential area with houses, a marina, and a flag.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
HK$1,647
HK$3,873 total
includes taxes & fees
28 Sept - 29 Sept
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
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 marina with boats docked, a clear sky, and a calm waterway.
A coastal residential area with houses, a marina, and a flag.

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
HK$1,565
HK$3,773 total
includes taxes & fees
28 Sept - 29 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A pier with a palm tree, clear turquoise water, and a distant shoreline.
A living room with a large TV, a balcony with a view of the sea, and a dining area with a table and chairs.
A resort with a swimming pool, a parking area, and a view of the ocean.
A beach with palm trees, a bench, and a clear view of the ocean.

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
HK$1,989
HK$3,662 total
includes taxes & fees
2 Oct - 3 Oct
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
A modern living space with a kitchen, dining area, and seating area.
A waterfront property with multiple buildings, a dock, and a clear view of the water.
A covered outdoor area with a table and chairs, a view of a body of water, and a white building in the background.

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
HK$1,771
HK$4,021 total
includes taxes & fees
27 Sept - 28 Sept
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A covered outdoor area with wicker furniture and string lights.

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
HK$1,359
HK$3,533 total
includes taxes & fees
28 Sept - 29 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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

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 1 day ago
Sugar Loaf Lodge
Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"The lady that checked me in was super cool. Had"
Kevin 1-night trip
Posted 3 days 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 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. 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 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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