Luxury Hotels in Summerland Key

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Luxury Hotels in Summerland Key

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

A beach scene with two white chairs, a hammock, and palm trees.

An aerial view of a resort with a large building, a beach, and a pier in the background.

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

1. Isla Bella Beach Resort & Spa

Marathon

Near the beach
2 bars
Full-service spa
Poolside bar
Concierge services

$209

$295 total

includes taxes & fees

Sep 13 - Sep 14

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

A room with two sofas, a round coffee table, and a small side table with a vase.

A spacious lobby with a central round table, surrounded by wicker chairs, large potted plants, and decorative lanterns.

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

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

Marathon

Near the beach
Ocean-view dining
Full-service spa
Poolside bar
Concierge services

$147

$203 total

includes taxes & fees

Sep 20 - Sep 21

A marina with boats docked, a pool area, and a building with a white facade.

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

A hotel room with a balcony overlooking a marina and the ocean.

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

3. Hilton Key West Resort & Marina

Stock Island

24-hour gym
Poolside bar
Concierge services

$106

$179 total

includes taxes & fees

Sep 16 - Sep 17

A dining table with plates of food, a drink, and a view of a pool and palm trees.

A hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

A person standing by a window overlooking a beach with palm trees and the ocean.

A beach with a palm tree and two chairs.

4. Margaritaville Beach House Key West

Key West

Direct access to the beach
Hot tub
Poolside bar
Concierge services

$178

$263 total

includes taxes & fees

Sep 23 - Sep 24

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

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

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.

5. Parrot Key Hotel & Villas

Northside Resort

Poolside bar
Concierge services

$129

$203 total

includes taxes & fees

Sep 16 - Sep 17

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.

6. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Near the beach
Poolside dining
24-hour gym
Poolside bar
Concierge services

$103

$150 total

includes taxes & fees

Sep 27 - Sep 28

A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.

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

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

7. Blue Flamingo Resort Key West

New Town

2 restaurants
Hot tub
2 poolside bars
Concierge services

$110

$180 total

includes taxes & fees

Sep 10 - Sep 11

A pool area with lounge chairs and a cabana.

A balcony with a table set for breakfast, overlooking the sea.

A hotel room with a bed, a sofa, a desk with a computer, a chair, and a view of the sea through large windows.

A dining area with a glass table, clear glass bottles, a bowl of fruit, and a wicker chair.

8. Ocean Key Resort - A Noble House Resort

Key West Historic District

Near the beach
2 restaurants
Full-service spa
Poolside bar
Concierge services

$220

$325 total

includes taxes & fees

Sep 28 - Sep 29

A large, ornate hotel with a pool, palm trees, and a view of the ocean.

A large, two-story house with a prominent tower and a covered porch.

A gated entrance with a blue metal gate, palm trees, and a building with a red roof in the background.

A grand staircase with ornate railings and a chandelier.

9. Southernmost House - Adult Exclusive

Old Town Key West

Near the beach
Ocean-view dining
Outdoor pool
Adults-only

$149

$294 total

includes taxes & fees

Oct 1 - Oct 2

A hotel with a swimming pool, balconies, and a view of the sea.

A balcony with a view of the ocean, a table, chairs, and a railing.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

10. Hyatt Centric Key West Resort and Spa

Key West Historic District

Near the beach
Ocean-view dining
Full-service spa
Poolside bar
Concierge services

$201

$296 total

includes taxes & fees

Sep 29 - Sep 30

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 spacious living room with a wooden coffee table, a striped sofa, and a television on a wooden cabinet.

11. Tranquility Bay Beachfront Hotel and Resort

Marathon

On private beach
3 outdoor pools

$191

$279 total

includes taxes & fees

Sep 30 - Oct 1

A bedroom with a bed, bedside table, lamp, and a small kitchenette. There is a balcony with wicker chairs and a glass table.

A pool area with lounge chairs and umbrellas, surrounded by buildings with balconies and a clear blue sky.

A spacious living area with a wooden staircase, a ceiling fan, a TV, and a view of the beach through an open door.

A spacious living area with a gray sofa, wooden staircase, and a kitchen in the background.

12. Eden House

Key West Historic District

Near the beach
Hot tub
Poolside bar
Concierge services

$127

$160 total

includes taxes & fees

Sep 10 - Sep 11

A beach with a wooden pier, palm trees, and beach umbrellas.

An outdoor dining area with tables set for guests, overlooking a calm sea and a pier.

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

An outdoor dining area with tables and chairs, overlooking the ocean.

13. The Reach Key West, Curio Collection by Hilton

Old Town Key West

On private beach
Full-service spa
Poolside bar
Concierge services

$180

$270 total

includes taxes & fees

Sep 22 - Sep 23

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

A spacious lobby with green sofas, a coffee table, and a dining area.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

14. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

On private beach
Full-service spa
2 outdoor pools
Concierge services

$246

$344 total

includes taxes & fees

Sep 16 - Sep 17

A beachfront hotel with a covered patio, palm trees, and a boat on the sand.

A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

A resort with a beach, a dock, and a water view.

15. Pier House Resort & Spa

Key West Historic District

On private beach
Beachfront dining
Full-service spa
Poolside bar
Concierge services

$290

$396 total

includes taxes & fees

Sep 17 - Sep 18

A large, white, two-story building with a balcony and a sign reading "The Marker Resort."

A resort with a swimming pool, lounge chairs, umbrellas, and palm trees.

A tropical setting with palm trees and a building with a white facade and dark roof.

A covered outdoor area with a pool, palm trees, and lounge chairs.

16. The Marker Key West Harbor Resort

Key West Historic District

Near the beach
Poolside dining
Poolside bar
Concierge services

$174

$259 total

includes taxes & fees

Sep 22 - Sep 23

A room with a view of the beach and ocean, a bed with a white and blue blanket, and a small table with a potted plant.

A beach scene with two people relaxing under a white umbrella, a palm tree, and a clear blue sky.

A beachside hotel with rows of blue lounge chairs and white umbrellas, palm trees, and a clear blue sky.

A beachside lounge with chairs and umbrellas, overlooking the ocean.

17. Southernmost Beach Resort and Guesthouses

Old Town Key West

Near the beach
Beachfront dining
Full-service spa
2 poolside bars
Concierge services

$145

$237 total

includes taxes & fees

Sep 16 - Sep 17

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.

A bar area with a counter, chairs, and a clock.

A couple walking along a poolside pathway surrounded by lush greenery.

18. The Gardens Hotel

Old Town Key West

Near the beach
2 bars
Poolside bar
Concierge services
Adults-only

$190

$214 total

includes taxes & fees

Sep 21 - Sep 22

A hotel with a covered entrance, multiple balconies, and palm trees.

A room with a stone wall, a wooden bench, a cactus, and a framed painting.

A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

19. Opal Key Resort & Marina, Key West

Old Town Key West

Near the beach
3 bars
Hot tub
Poolside bar
Concierge services

$259

$331 total

includes taxes & fees

Sep 10 - Sep 11

A pool area with lounge chairs and palm trees.

A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.

A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

A sign for Santa Maria Resort surrounded by lush greenery and palm trees.

20. Santa Maria Suites

Old Town Key West

Poolside bar
Concierge services

$279

$381 total

includes taxes & fees

Sep 13 - Sep 14

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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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