Lower Florida Keys Holiday Rentals, Florida: Private House Rentals

A coastal landscape with clear turquoise waters, a long bridge, and a small island with buildings.

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Go beyond your typical stay in Lower Florida Keys

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Our top choices for Lower Florida Keys hotels

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

1. Margaritaville Beach House Key West

Key West

TRICIA LYNN

฿6,986

฿9,968 total

includes taxes & fees

27 Sept - 28 Sept

A waterfront building with a flat roof, large windows, and a balcony.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

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

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

2. Sugar Loaf Lodge

Summerland Key

Kevin

฿3,314

฿3,728 total

includes taxes & fees

27 Sept - 28 Sept

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

3. Hilton Key West Resort & Marina

Stock Island

Molly

฿3,972

฿6,472 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

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

4. Hampton Inn Key West FL

Key West

Rabia

฿5,091

฿5,727 total

includes taxes & fees

1 Oct - 2 Oct

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

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.

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

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

New Town

Patricia

฿4,187

฿5,652 total

includes taxes & fees

1 Oct - 2 Oct

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

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

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

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

6. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,867

฿6,395 total

includes taxes & fees

27 Sept - 28 Sept

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

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

Esteban

฿3,955

฿6,332 total

includes taxes & fees

27 Sept - 28 Sept

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

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

8. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Craige

฿3,990

฿5,618 total

includes taxes & fees

1 Oct - 2 Oct

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A beach with palm trees, clear blue water, and a pier extending into the sea.

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

A spacious lobby with a marble floor, leather sofas, and large potted plants.

9. Beachside Resort & Residences

Key West

James

฿2,922

฿6,488 total

includes taxes & fees

27 Sept - 28 Sept

A swimming pool with lounge chairs and palm trees.

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

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

10. Hilton Garden Inn Key West / The Keys Collection

New Town

Walt

฿3,532

฿4,915 total

includes taxes & fees

4 Oct - 5 Oct

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

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

11. Ibis Bay Beach Resort

Northside Resort

Stephanie

฿3,394

฿4,898 total

includes taxes & fees

27 Sept - 28 Sept

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

A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

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

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

12. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿5,991

฿6,740 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

A multi-story hotel with balconies and a well-lit entrance.

A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.

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

13. The Laureate Key West

New Town

Mailyn

฿5,322

฿6,929 total

includes taxes & fees

27 Sept - 28 Sept

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.

14. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿4,418

฿6,891 total

includes taxes & fees

4 Oct - 5 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 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.

15. Looe Key Reef Resort

Summerland Key

Michel

฿2,529

฿2,845 total

includes taxes & fees

27 Sept - 28 Sept

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

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

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

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

16. Havana Cabana at Key West

New Town

Silvia

฿3,715

฿6,292 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

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

17. Artist House Key West

Key West Historic District

NATHAN

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 marina with jet skis docked in front of a hotel with a dock and a boat in the background.

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.

18. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

฿6,962

฿10,167 total

includes taxes & fees

28 Sept - 29 Sept

A building with a white exterior, a large red awning, and a gated entrance.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

A paved pathway lined with various plants and trees, leading to a building with a beige exterior.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

19. Authors of Key West Guest House

Key West Historic District

Avamarie

฿2,736

฿3,079 total

includes taxes & fees

27 Sept - 28 Sept

A bright green porch with hanging planters, a wooden chair, and a railing.

A bar area with a wooden counter, colorful decorations, and a sign with motivational ocean-themed text.

A brightly colored Caribbean house with a balcony, a sign indicating it's for rent, and bicycles parked outside.

20. Caribbean House

Old Town Key West

David

฿3,368

฿4,626 total

includes taxes & fees

27 Sept - 28 Sept

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Holiday Rentals in Lower Florida Keys

Holiday Home

Two people sitting by a pool with palm trees in the background.

A thatched-roof structure surrounded by palm trees and blue chairs.

A modern kitchen with grey cabinets, a white countertop, and a built-in microwave.

A modern kitchen with a TV, white bar stools, and a shower area.

Sugarloaf Key RV Resort & Cottages

Summerland Key

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

Cottage

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 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.

Old Wooden Bridge Resort and Marina

Punta Brisa

"Nice place"

Mobile Home

A clear view of a kayak on the water with a person paddling, a distant bridge, and a clear sky.

A beach with palm trees and a clear view of the ocean.

A compact room with a gray sofa, a small table, and two turquoise stools. A large round window offers a view of the sea and a thatched-roof structure.

A compact kitchen with a dining area, a staircase, and a view of the sea.

Sunshine Key RV Resort & Marina

Big Pine Key

"Excellent property. Location is great. Ambient feels familiar and pacefully"

Aparthotel

Island View 1BR Residence With Balcony

Key West

"Great place it is a full apartment with everything you could need and very clean "

Aparthotel

A lobby with a reception desk, a bar area, and a sign that reads "Tavern Town".

A coastal hotel with multiple buildings, a swimming pool, and a marina with boats.

Resort View 1BR Suite

Key West

"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "

Aparthotel

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

A modern kitchen with dark cabinetry, stainless steel appliances, and a central island.

Ocean Front 1BR Suite With Direct Beach Access

Key West

"Clean and spacious. Great view from room!"

Aparthotel

Two Bedroom Residence With Balcony

Key West

"The roosters crowing early morning was irritating "

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Stay near popular Lower Florida Keys attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

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A beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)

Nothing says holiday like spending a care-free day in Florida Keys Beaches, a popular beach in Long Beach Estates.

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Southernmost Point

8.8/10 (17,214 reviews)

Snap a memorable photograph from the edge of North America at this monumental landmark.

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Mallory Square

9.2/10 (15,939 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

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A vintage typewriter on a wooden table with a notebook and pen beside it.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)

The displays of old weapons and interpretive panels in a fort at the heart of the southernmost state park in the continental U.S. provide information about the Civil War.

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A beachside resort with palm trees, a large white building, and a checkered pattern on the sand.

South Beach

8.4/10 (5,461 reviews)

The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

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Learn more about Lower Florida Keys

Discover the local area in Lower Florida Keys as you check out popular sights like Florida Keys Beaches and Duval Street.

See all hotels in Lower Florida Keys

Top Lower Florida Keys Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

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

Looe Key Reef Resort

10/10 Excellent

"The lady that checked me in was super cool. Had"

Sugarloaf Key RV Resort & Cottages

8/10 Good

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

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Extraordinarily clean and well maintained. We stayed in the hotel which was well thought out"

More cheap stays in Lower Florida Keys

Alexander Palms Court

715 South St Key West FL

฿3,991

฿4,490 total

27 Sept - 28 Sept

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿3,394

฿4,898 total

27 Sept - 28 Sept

includes taxes & fees

8.2/10 Very good! (2,388 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,091

฿5,727 total

1 Oct - 2 Oct

includes taxes & fees

9/10 Wonderful! (1,523 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

฿4,169

฿5,820 total

27 Sept - 28 Sept

includes taxes & fees

8.6/10 Excellent! (1,386 reviews)

Pegasus International Hotel

501 Southard Street Key West FL

฿3,670

฿5,823 total

1 Oct - 2 Oct

includes taxes & fees

8.2/10 Very good! (1,005 reviews)

Parmer's Resort

565 Barry Avenue Summerland Key FL

฿4,802

฿6,492 total

8 Oct - 9 Oct

includes taxes & fees

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Book Hotels in Lower Florida Keys on Expedia.com

Find hotels in Lower Florida Keys, FL from ฿3,079

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Lower Florida Keys

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Lower Florida Keys hotels

1. Margaritaville Beach House Key West

2. Sugar Loaf Lodge

3. Hilton Key West Resort & Marina

4. Hampton Inn Key West FL

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

6. The Perry Hotel & Marina Key West

7. Blue Flamingo Resort Key West

8. DoubleTree Resort by Hilton Grand Key - Key West

9. Beachside Resort & Residences

10. Hilton Garden Inn Key West / The Keys Collection

11. Ibis Bay Beach Resort

12. Courtyard by Marriott Key West Waterfront

13. The Laureate Key West

14. Parrot Key Hotel & Villas

15. Looe Key Reef Resort

16. Havana Cabana at Key West

17. Artist House Key West

18. Hyatt Centric Key West Resort and Spa

19. Authors of Key West Guest House

20. Caribbean House

Holiday Rentals in Lower Florida Keys

Sugarloaf Key RV Resort & Cottages

Old Wooden Bridge Resort and Marina

Sunshine Key RV Resort & Marina

Island View 1BR Residence With Balcony

Resort View 1BR Suite

Ocean Front 1BR Suite With Direct Beach Access

Two Bedroom Residence With Balcony

Stay near popular Lower Florida Keys attractions

Duval Street

Florida Keys Beaches

Southernmost Point

Mallory Square

Smathers Beach

Ernest Hemingway Home and Museum

Fort Zachary Taylor Historic State Park

South Beach

Learn more about Lower Florida Keys

Top Lower Florida Keys Hotel Reviews

Sugar Loaf Lodge

Looe Key Reef Resort

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key Hotel at KOA Resort

More cheap stays in Lower Florida Keys

Alexander Palms Court

Ibis Bay Beach Resort

Hampton Inn Key West FL

Southwinds Motel

Pegasus International Hotel

Parmer's Resort

Explore a world of travel with Expedia

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