Summerland Key Holiday Rentals, Florida: Private House Rentals

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

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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 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.

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

1. Parmer's Resort

Summerland Key

Mireya

3.291.254 ₫

4.550.616 ₫ 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 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.

2. Sugar Loaf Lodge

Summerland Key

Richard

3.092.453 ₫

3.479.140 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

3. Looe Key Reef Resort

Summerland Key

Stephen

2.621.828 ₫

2.949.556 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

4. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

6.046.482 ₫

16.289.172 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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.

5. Atlantic View Luxury Villa with Pool

Summerland Key

Preetam

13.448.272 ₫

25.361.688 ₫ total

includes taxes & fees

9 Oct - 10 Oct

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

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.

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

6. Isla Bella Beach Resort & Spa

Marathon

Andrew

4.654.272 ₫

6.767.210 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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.

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

7. Old Wooden Bridge Resort and Marina

Punta Brisa

Daisybel

3.484.857 ₫

7.574.887 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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.

8. Hilton Key West Resort & Marina

Stock Island

Molly

3.281.638 ₫

5.212.082 ₫ total

includes taxes & fees

12 Oct - 13 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 hotel entrance with a palm tree-lined driveway, a vintage car, and a metal canopy structure.

9. Margaritaville Beach House Key West

Key West

TRICIA LYNN

5.431.283 ₫

7.750.006 ₫ total

includes taxes & fees

5 Oct - 6 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 poolside area with lounge chairs, blue umbrellas, and a fire pit.

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

amy

3.721.338 ₫

5.096.050 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

Marathon

Rick

4.240.559 ₫

5.748.520 ₫ total

includes taxes & fees

11 Oct - 12 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 beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

12. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Tina

5.407.375 ₫

7.252.712 ₫ total

includes taxes & fees

26 Oct - 27 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 two-story building with a balcony, arched windows, and a green roof.

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

13. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

5.407.375 ₫

7.252.712 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

14. Hampton Inn Key West FL

Key West

Jaycie

4.391.803 ₫

4.940.778 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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

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

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.

15. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Nancy

3.201.598 ₫

4.478.859 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A swimming pool surrounded by palm trees and lounge chairs.

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

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

16. Tranquility Bay Beachfront Hotel and Resort

Marathon

Stuart

5.592.402 ₫

7.962.156 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

New Town

Patricia

3.484.857 ₫

4.651.218 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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 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.

18. Parrot Key Hotel & Villas

Northside Resort

Anthony

3.430.284 ₫

5.350.203 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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

A waterfront hotel with multiple balconies, a dock, and boats.

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.

19. Opal Key Resort & Marina, Key West

Old Town Key West

Susan

6.730.633 ₫

8.595.460 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A pool area with lounge chairs and a cabana.

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

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 waterfront hotel with a long pier, multiple balconies, and a view of the ocean.

20. Ocean Key Resort - A Noble House Resort

Key West Historic District

Patrick

7.510.243 ₫

10.466.395 ₫ total

includes taxes & fees

7 Oct - 8 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

10/10 Excellent

"The room was super clean. The fact that we can keep a boat docked right behind our room is amazing. There is a tiki bar literally right in front of the room is a plus. Check out was easy and quick as well as check in. I mean best decision ever."

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!!"

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Room was clean, we used the pool, hot tub, marina boat rental, bar, store and the beach area. Everything was very nice. It’s a short ride to Bahia Honda beaches and Key West. The bar, marina and store were all very nice and useful."

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"