Pet-Friendly Hotels in Summerland Key

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Pet-Friendly Hotels in Summerland Key

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

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

A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

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

1. Looe Key Reef Resort

Summerland Key

$76

$85 total

includes taxes & fees

Oct 5 - Oct 6

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.

2. Parmer's Resort

Summerland Key

$144

$194 total

includes taxes & fees

Oct 4 - Oct 5

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

A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.

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

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

3. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

$233

$627 total

includes taxes & fees

Oct 5 - Oct 6

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

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

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

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

4. Atlantic View Luxury Villa with Pool

Summerland Key

$575

$1,041 total

includes taxes & fees

Oct 3 - Oct 4

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

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

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

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

5. Old Wooden Bridge Resort and Marina

Punta Brisa

$201

$367 total

includes taxes & fees

Oct 1 - Oct 2

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

A waterfront hotel with a pool, palm trees, and a wooden dock.

6. Hilton Key West Resort & Marina

Stock Island

$126

$202 total

includes taxes & fees

Oct 6 - Oct 7

A swimming pool surrounded by palm trees and a natural rock formation.

A covered outdoor seating area with a pool in the background.

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

7. Havana Cabana at Key West

New Town

$111

$188 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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

A bar area with a thatched roof, wooden chairs, and a poolside view.

8. Hampton Inn Key West FL

Key West

$166

$186 total

includes taxes & fees

Oct 6 - Oct 7

A swimming pool with lounge chairs and palm trees.

A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

A modern living room with a sectional sofa, a small round table, and a potted plant.

9. Hilton Garden Inn Key West / The Keys Collection

New Town

$106

$147 total

includes taxes & fees

Oct 6 - Oct 7

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

A tall palm tree with a white building in the background.

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.

10. Parrot Key Hotel & Villas

Northside Resort

$132

$206 total

includes taxes & fees

Oct 6 - Oct 7

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.

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

11. Blue Flamingo Resort Key West

New Town

$110

$180 total

includes taxes & fees

Oct 1 - Oct 2

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

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

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.

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

Marathon

$135

$187 total

includes taxes & fees

Oct 8 - Oct 9

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

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

13. Margaritaville Beach House Key West

Key West

$209

$298 total

includes taxes & fees

Oct 1 - Oct 2

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.

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

$127

$177 total

includes taxes & fees

Oct 6 - Oct 7

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

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

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

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

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

Marathon

$163

$221 total

includes taxes & fees

Oct 1 - Oct 2

A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

A pool with a lion head sculpture in the center.

A patio area with white metal tables and chairs, surrounded by potted plants and palm trees.

16. Artist House Key West

Key West Historic District

$249

$280 total

includes taxes & fees

Oct 21 - Oct 22

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

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

A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

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

17. The Perry Hotel & Marina Key West

Stock Island

$137

$215 total

includes taxes & fees

Oct 5 - Oct 6

A pool area with a brick patio, potted plants, and a covered seating area.

A view through a glass door with a metal handle, leading to a white fence and a blue car parked outside.

A white picket fence, a palm tree, and a sign reading "Garden House Key West".

A porch with a white chair, a wooden door, and a small indoor dining area visible through the door.

18. The Garden House

Key West Historic District

$99

$133 total

includes taxes & fees

Oct 1 - Oct 2

A wooden boardwalk leading to a beach with palm trees and a clear sky.

An outdoor patio with wicker furniture and a ceiling fan, surrounded by lush greenery and a view of a residential area.

A large white building with a balcony, palm trees, and a brick pathway leading to the entrance.

A grand room with a large wooden door, a fireplace with a mantelpiece, and a chandelier.

19. Amsterdam's Curry Mansion Inn

Key West Historic District

$144

$162 total

includes taxes & fees

Oct 5 - Oct 6

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A compact kitchen with white cabinets, a microwave, and a small dining area with two wicker chairs.

A pink building with a white door, a balcony with a white railing, and a view of a pool area.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

20. The Palms Hotel

Old Town Key West

$134

$173 total

includes taxes & fees

Oct 1 - Oct 2

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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 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 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 long bridge over turquoise waters with a few vehicles on it.

Bay Point

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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 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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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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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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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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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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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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