Hotels with a Pool in Summerland Key

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Hotels with a Pool in Summerland Key

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 sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

1. Looe Key Reef Resort

Summerland Key

Outdoor pool
Poolside bar
Pool loungers
Near the beach

$79

$89 total

includes taxes & fees

Oct 12 - Oct 13

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 reception area with a wooden sculpture, a reception desk, a computer, and a television.

A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

2. Sugar Loaf Lodge

Summerland Key

Outdoor pool

$119

$134 total

includes taxes & fees

Sep 13 - Sep 14

A sunset view with a thatched structure and a palm tree by a calm body of water.

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.

Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

3. Parmer's Resort

Summerland Key

Outdoor pool
Pool loungers
On private beach

$127

$175 total

includes taxes & fees

Sep 27 - Sep 28

A residential property with a swimming pool, a covered patio, and a view of the ocean.

A concrete pathway flanked by lush green foliage, leading to a shaded area.

A two-story building with a balcony, surrounded by tropical vegetation.

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

4. Atlantic View Luxury Villa with Pool

Summerland Key

10 outdoor pools
Pool loungers
Near the beach
Hot tub

$575

$1,041 total

includes taxes & fees

Sep 14 - Sep 15

A poolside area with lounge chairs and a view of boats in the background.

A clear view of turquoise ocean water and a blue sky with clouds.

A marina with numerous boats docked, a swimming pool, and palm trees.

A breakfast setting with a table, chairs, a vase with flowers, and a city view.

5. Hilton Key West Resort & Marina

Stock Island

6 outdoor pools
Poolside bar
Pool loungers

$106

$179 total

includes taxes & fees

Sep 17 - Sep 18

A blue chair with a sign reading "CaptainPips.com" and a website address.

A waterfront dock with boats and a sunset.

A room with a wooden table and chairs, a sliding glass door leading to a balcony, and a blue cooler on the floor.

A beach with a wooden pier, palm trees, and a clear blue sky.

6. Captain Pips Marina & Hideaway

Marathon

Outdoor pool
Pool loungers
Near the beach

$93

$132 total

includes taxes & fees

Sep 12 - Sep 13

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A balcony with wicker furniture and a view of the ocean and palm trees.

7. Hampton Inn Key West FL

Key West

Outdoor pool
Poolside bar
Pool loungers
Near the beach

$118

$133 total

includes taxes & fees

Sep 16 - Sep 17

A neatly made bed with a grey and white duvet, a wooden headboard, and a bedside table with a lamp and remote control.

A compact living space with a kitchenette, dining area, and seating area.

A spacious living room with a wooden floor, a sofa, a TV, a cabinet, and a sliding glass door leading to a balcony.

A kitchen with wooden cabinets, a stainless steel refrigerator, a granite countertop, a sink, a microwave, a stove, and a clock.

8. Knight's Key Suites

Marathon

Outdoor pool

$69

$99 total

includes taxes & fees

Sep 14 - Sep 15

An aerial view of a resort with a central pool, multiple buildings, and a beach area with sun loungers.

A bar area with wooden chairs, a bar counter, and a variety of bottles and glasses.

A beach with white chairs and kayaks, palm trees, and a clear view of the ocean.

9. Isla Bella Beach Resort & Spa

Marathon

5 outdoor pools
Poolside bar
Pool loungers
Near the beach
Full-service spa

$199

$283 total

includes taxes & fees

Sep 13 - Sep 14

A clear blue pool with white lounge chairs and palm trees, overlooking a calm sea.

An aerial view of a coastal resort with a marina, palm trees, and a large building complex.

A row of blue hammocks on a sandy beach with palm trees and a clear sky.

A bar area with a view of the ocean, bar stools, umbrellas, and a variety of bottles.

10. Courtyard by Marriott Faro Blanco Resort, Marathon Florida Keys

Marathon

2 outdoor pools
Poolside bar
Pool loungers
On the beach
Hot tub

$135

$187 total

includes taxes & fees

Sep 27 - Sep 28

A swimming pool with lounge chairs, palm trees, and a lighthouse in the background.

An outdoor dining area with tables and chairs, a pool, and a view of the sea and boats.

A bar area with a long counter, multiple bar stools, and a view of the marina with boats and palm trees.

A marina with boats docked, a lighthouse, and a resort with outdoor seating.

11. Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Marathon

4 outdoor pools
Poolside bar
Pool loungers
Near the beach
Full-service spa

$147

$203 total

includes taxes & fees

Sep 20 - Sep 21

A fenced pool area with palm trees, a blue and white tiled walkway, and a sign indicating pool hours.

A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

12. Old Wooden Bridge Resort and Marina

Punta Brisa

Outdoor pool
Pool loungers
Near the beach

$100

$253 total

includes taxes & fees

Sep 27 - Sep 28

A resort with a pool, lounge chairs, and a view of the ocean.

A deck with tables and chairs, overlooking a calm body of water and palm trees.

A modern kitchen with dark countertops, stainless steel appliances, and wooden cabinets.

A dock with boats, a wooden pier, and a distant shoreline with palm trees.

13. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Marathon

Outdoor pool
Poolside bar
Pool loungers
Near the beach
Hot tub

$134

$179 total

includes taxes & fees

Sep 20 - Sep 21

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

An outdoor patio with tables and chairs, umbrellas, and palm trees.

A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

14. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Outdoor pool
Poolside bar
Pool loungers
Near the beach

$103

$150 total

includes taxes & fees

Sep 27 - Sep 28

A pool area with blue lounge chairs, a hot tub, and a covered seating area.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

A marina with boats docked, a beach resort building, and palm trees.

A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.

15. Ibis Bay Beach Resort

Northside Resort

Outdoor pool
Poolside bar
Pool loungers
On private beach

$101

$146 total

includes taxes & fees

Sep 13 - Sep 14

A clear blue pool surrounded by lounge chairs and umbrellas, with palm trees and a gazebo in the background.

A couple holding hands in a tropical setting with palm trees and greenery.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

16. Blue Flamingo Resort Key West

New Town

2 outdoor pools
2 poolside bars
Pool loungers
Hot tub

$110

$180 total

includes taxes & fees

Sep 13 - Sep 14

A poolside area with two covered seating areas labeled "Sugarloaf" and "Boca Grande," surrounded by palm trees and a clear blue pool.

A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

17. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

New Town

Outdoor pool
Poolside bar

$109

$151 total

includes taxes & fees

Sep 17 - Sep 18

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A beach with palm trees, lounge chairs, and umbrellas.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.

18. Parrot Key Hotel & Villas

Northside Resort

4 outdoor pools
Poolside bar
Pool loungers

$129

$203 total

includes taxes & fees

Sep 17 - Sep 18

A swimming pool surrounded by palm trees and lounge chairs.

A beach scene with a wooden deck, palm trees, and a gazebo-like structure.

An aerial view of a resort with a central swimming pool, surrounded by lush greenery and palm trees, with a view of the ocean.

A wooden deck with blue chairs overlooking a beach with palm trees and the ocean.

19. Tranquility Bay Beachfront Hotel and Resort

Marathon

3 outdoor pools
Pool loungers
On private beach

$191

$279 total

includes taxes & fees

Oct 1 - Oct 2

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

A beach view with a wooden pier, palm trees, and a sunset over the water.

A balcony with wicker furniture, a view of the water, and a railing.

A balcony with wicker furniture, a red chair, and a lamp.

20. Beachside Resort & Residences

Key West

Outdoor pool
Poolside bar
Pool loungers
On private beach
Hot tub

$103

$212 total

includes taxes & fees

Sep 13 - Sep 14

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Discover your perfect hotel with a pool in Summerland Key

Breakfast included

4 stars

Hot tub

5 stars

Spa

Top neighborhoods in Summerland Key

A calm lake with several white birds, including herons and pelicans, on the water's edge.

A beach with dead trees and a calm sea at sunset.

Cutthroat Harbor Estates

Escape the tourist rush at Cutthroat Harbor Estates, a peaceful slice of paradise on Summerland Key. This residential waterfront neighborhood offers crystal-clear waters perfect for fishing, kayaking, and boating from your private dock. The low-rise coastal homes on stilts create a genuine Keys atmosphere where you can spot tropical birds and enjoy breathtaking sunset views. You'll need to drive to nearby Cudjoe Key or Summerland Key for dining options featuring fresh seafood and Caribbean flavors. Vacation rental homes with waterfront views dominate accommodation choices. The neighborhood's layout prioritizes privacy and seclusion, making it ideal for travelers seeking the authentic Florida Keys lifestyle.

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A waterfront property with a pool, palm trees, and a building with a white roof.

A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

A waterfront property with multiple houses, palm trees, and a calm sea.

A boat docked near a waterfront with a house and palm trees in the background.

A waterfront with a pier, calm water, and houses with palm trees in the background.

Sugarloaf Shores

Sugarloaf Shores delivers waterfront paradise without the tourist crowds. Private canals weave between stilted homes where you can launch kayaks right from your rental's backyard dock. The crystal-clear backcountry waters beckon with world-class fishing, while gentle waves provide perfect spots for swimming and snorkeling. Dining and shopping require a short drive, as this peaceful residential enclave focuses on natural beauty rather than commercial offerings. Most visitors stay in spacious vacation homes with private pools and boat docks. A rental car is essential for exploring the rest of the Florida Keys from this secluded waterfront haven.

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An aerial view of a bridge over turquoise water.

Cudjoe Gardens

Cudjoe Gardens offers a slice of authentic Florida Keys living with canal-front homes where you can park your boat right out back. This peaceful residential retreat lets you escape the crowds while still having easy access to the surrounding waters. Wildlife enthusiasts will spot herons stalking the shallows and fish jumping at sunrise while the gentle sound of water lapping against docks creates your vacation soundtrack. Nearby restaurants in Summerland Key and Cudjoe Key serve up fresh seafood just a short drive away. Most homes feature private pools, boat docks, and tropical landscaping, all designed for relaxation and water activities. A rental car is essential for exploring the area, as this quiet community focuses on waterfront living rather than tourist amenities.

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An aerial view of a long bridge over turquoise waters with a few vehicles on it.

Bay Point

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An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

Breezeswept Beach Estates is a slice of Florida Keys paradise where private docks and waterfront homes replace tourist traps. You'll spend your days exploring crystal-clear waters, spotting marine life while kayaking, or casting a line into the Gulf. The surrounding Newfound Harbor Keys and nearby islands offer perfect day-trip adventures when you're ready to venture beyond your peaceful retreat. Vacation rentals with tropical landscaping and breezy porches make up the accommodation options here. You'll need a car to reach restaurants on Ramrod Key or stock up on groceries for cooking. The quiet streets and gentle waves create the perfect soundtrack for stargazing and disconnecting from the everyday hustle.

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Top landmarks in Summerland Key

Sugarloaf Beach

8.4/10 (38 reviews)

Whether you want to collect beach glass or watch the sunset, Sugarloaf Beach is a spot you might want to check out, located 8.1 mi (13 km) from central Summerland Key. Catch the sunset by the shore at Florida Keys Beaches, just a short walk away.

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Upper Sugarloaf Key

8.6/10 (54 reviews)

Upper Sugarloaf Key is 5.2 mi (8.3 km) from central Summerland Key, why not stop by during your stay.

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Pye Key

Pye Key is 1.9 mi (3 km) from central Summerland Key, why not stop by during your stay.

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Upper Sugarloaf Sound

9.2/10 (17 reviews)

Listen to the relaxing sound of the water and take some great vacation pics at Upper Sugarloaf Sound located 6.3 mi (10.2 km) from central Summerland Key.

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Venture Key

Venture Key is 1.7 mi (2.8 km) from central Summerland Key, why not stop by during your stay.

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Crab Key

Crab Key is 1.4 mi (2.3 km) from central Summerland Key, why not stop by during your stay.

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Squirrel Key

Squirrel Key is 11.3 mi (18.1 km) from central Summerland Key, why not stop by during your stay.

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Boondocks Grille & Draft House

You could stop off for a few afternoon drinks at Boondocks Grille & Draft House when visiting Summerland Key.

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