Best Summerland Key Hotels in 2026 from HK$838 - Fully Refundable Options

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

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Go beyond your typical stay in Summerland Key

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Our top choices for Summerland Key hotels

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

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

A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.

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

Summerland Key

Mireya

HK$1,194

HK$1,599 total

includes taxes & fees

1 Nov - 2 Nov

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.

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

2. Sugar Loaf Lodge

Summerland Key

Richard

HK$934

HK$1,051 total

includes taxes & fees

12 Oct - 13 Oct

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

A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

A canal with boats docked on both sides, surrounded by lush greenery and trees.

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

3. Looe Key Reef Resort

Summerland Key

Stephen

HK$792

HK$891 total

includes taxes & fees

14 Oct - 15 Oct

A wooden deck with a railing, wicker chairs, and a view of greenery.

A two-story house with a balcony and a staircase leading to the upper level.

A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.

A modern kitchen with a large island, white cabinetry, and three wicker bar stools.

4. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

HK$2,323

HK$5,478 total

includes taxes & fees

14 Oct - 15 Oct

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

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

A large house with a pool, surrounded by lush greenery.

A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

5. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

HK$4,061

HK$7,659 total

includes taxes & fees

9 Oct - 10 Oct

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

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

A hotel room with a balcony, a bed, a desk, and two chairs.

6. Hampton Inn Key West FL

Key West

Jaycie

HK$1,423

HK$1,601 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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

A modern office space with a reception desk, computer, and seating area.

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

New Town

Brian

HK$982

HK$1,325 total

includes taxes & fees

14 Oct - 15 Oct

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

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

A row of houseboats docked at a marina with clear reflections in the water.

A floating houseboat with a covered deck and seating area, docked at a marina.

8. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

HK$688

HK$1,878 total

includes taxes & fees

12 Oct - 13 Oct

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.

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

Andrew

HK$2,112

HK$2,862 total

includes taxes & fees

19 Oct - 20 Oct

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

A covered outdoor area with wooden tables and chairs, a view of the water, and a wooden deck with railings.

A modern restaurant with a wooden counter, seating area, and large windows.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

10. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

HK$1,439

HK$1,619 total

includes taxes & fees

26 Oct - 27 Oct

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

A beach with a palm tree and two chairs.

A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

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

11. Margaritaville Beach House Key West

Key West

James Joseph

HK$1,640

HK$2,340 total

includes taxes & fees

12 Oct - 13 Oct

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 covered outdoor seating area with tables and chairs, overlooking a marina with boats.

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

12. Hilton Key West Resort & Marina

Stock Island

Molly

HK$927

HK$1,502 total

includes taxes & fees

14 Oct - 15 Oct

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

13. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

HK$1,633

HK$2,190 total

includes taxes & fees

26 Oct - 27 Oct

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

A hotel with a central courtyard, palm trees, and a fountain.

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

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

14. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

HK$998

HK$1,388 total

includes taxes & fees

14 Oct - 15 Oct

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

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

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

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

15. Ibis Bay Beach Resort

Northside Resort

Andre

HK$898

HK$1,264 total

includes taxes & fees

11 Oct - 12 Oct

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

A spacious living area with a large window, a dining table, and comfortable seating.

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

A two-story building with a balcony, arched windows, and a green roof.

16. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

HK$1,633

HK$2,190 total

includes taxes & fees

28 Oct - 29 Oct

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

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

17. Blue Flamingo Resort Key West

New Town

Esteban

HK$927

HK$1,485 total

includes taxes & fees

11 Oct - 12 Oct

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

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

A modern bar area with a central island, white bar stools, and a view of the ocean.

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

18. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

HK$1,394

HK$2,098 total

includes taxes & fees

25 Oct - 26 Oct

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

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

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

19. The Perry Hotel & Marina Key West

Stock Island

Jade

HK$868

HK$1,455 total

includes taxes & fees

25 Oct - 26 Oct

Two hammocks on a sandy beach with a clear blue sky and turquoise water.

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

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

A poolside area with lounge chairs, blue umbrellas, and a fire pit.

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

Marathon

amy

HK$1,124

HK$1,539 total

includes taxes & fees

14 Oct - 15 Oct

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Where to stay in Summerland Key

Find the best Summerland Key areas for the activities you enjoy most.

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

Cutthroat Harbour Estates offers a tranquil slice of Florida Keys living with private boat docks and crystal-clear waters. This residential waterfront area provides an authentic escape from tourist crowds. Homes on stilts with weathered wood docks create a classic Keys atmosphere. The neighborhood's canals connect directly to the Gulf, making it perfect for fishing and boating enthusiasts. Gentle waves lap against private docks while tropical birds call at dawn. Nearby Venture Out Keys and Summerland Key provide dining options and additional sights.

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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 coastal view with houses and palm trees.

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.

Sugarloaf Shores

Sugarloaf Shores offers a tranquil escape on the Florida Keys waterfront. Private homes line peaceful canals where turquoise waters invite fishing, kayaking, and boating adventures. This residential haven sits away from tourist crowds yet provides easy access to stunning ocean views. The neighborhood's charm lies in its authentic Keys lifestyle with homes on stilts and tropical landscaping. Nearby Sugarloaf Beach and Lower Sugarloaf Sound provide perfect spots for swimming and snorkelling. Visitors appreciate the quiet streets for evening strolls and stargazing.

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

Bay Point

While Bay Point may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Lower Sugarloaf Sound and Florida Keys Beaches.

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An aerial view of a bridge over turquoise water.

Cudjoe Gardens

Cudjoe Gardens offers a peaceful waterfront retreat in the Florida Keys. This quiet residential haven features canal-front properties with private docks for easy boat access. Travellers can enjoy fishing, wildlife watching, and stargazing from their holiday rentals. The neighborhood's tropical charm comes alive with pastel homes on stilts surrounded by palm trees and native plants. A hire car is essential for exploring nearby Summerland Key attractions and dining options. Water enthusiasts will appreciate direct canal access to open waters and nearby beaches.

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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

Escape to the peaceful shores of Breezeswept Beach Estates on Summerland Key. This residential haven offers private waterfront properties with boat docks and direct access to crystal-clear Florida waters. The neighborhood's charm lies in its quiet streets lined with pastel homes and tropical landscaping. Outdoor enthusiasts will love exploring nearby Newfound Harbour Keys by kayak or boat. Fish in the shallow waters, spot native birds, or simply relax under swaying palms. With minimal commercialization and abundant natural beauty, this peaceful retreat captures authentic Keys living without the tourist crowds.

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Stay near popular Summerland Key attractions

Sugarloaf Beach

8.4/10 (38 reviews)

This secluded private beach on Sugarloaf Key offers a tranquil escape from the busier Florida Keys shorelines. Guests enjoy pristine views and peaceful sunbathing in a natural, amenity-light setting.

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Upper Sugarloaf Key

8.6/10 (54 reviews)

Upper Sugarloaf Key serves as a gateway to the Great White Heron National Wildlife Refuge with pristine waters. Kayak through mangroves at dawn to spot diverse bird species in this tranquil Florida Keys ecosystem.

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Upper Sugarloaf Sound

9.2/10 (17 reviews)

Glide through Upper Sugarloaf Sound's tranquil waters surrounded by vibrant mangroves and diverse birdlife. Kayak or paddleboard this peaceful Florida Keys retreat to experience nature at its most serene.

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Crab Key

Crab Key is a private residential island off Summerland Key in the Florida Keys with no public access. This exclusive enclave remains one of the few truly private islands in the Keys.

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Venture Key

This private Florida Keys community offers waterfront holiday rentals with direct access to pristine boating waters. Enjoy the heated pool and tennis courts before setting out from the marina for a day of fishing.

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Pye Key

This unspoiled island near Summerland Key offers pristine waters for snorkelling and marine life observation. Bring supplies and reef-safe sun cream for your half-day adventure in this natural Florida Keys sanctuary.

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Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.

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Boondocks Grille & Draft House

Boondocks Grille & Draft House is just one of the places to see in Summerland Key, so why not enjoy the other things to explore during your travels?

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Learn more about Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favourite seafood shacks serving fresh-caught Keys lobster.

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A coastal pier extending into the sea, surrounded by rocky shores and greenery.

Top Summerland Key Hotel Reviews

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."

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!!"

Direct Oceanfront Cottage-Sunrise View- #2,

8/10 Good

"Convenient location."

Sugar Loaf Lodge

10/10 Excellent

"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"

Sugarloaf Key RV Resort & Cottages

8/10 Good

"Nice for a chill weekend in the lower keys and for people with family accompanying them"

Cottage with Pool and Boat Dockage just minutes to Key West!

10/10 Excellent

"This is a Keys property that allows pets. That's rare when you're looking to stay with a boat for a week.Use the Cudjoe Gardens Marina for a boat ramp unless you have a light boat and 4 wheel drive.The pool is a nice amenity to cool off in!The AC works well and the TV/WiFi does too."

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

10/10 Excellent

"Amazing place to stay"

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Great host ! Few snags but it all worked out great."

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"The house was clean with plenty of room for everyone."