Stock Island Holiday Rentals, Key West: Private House Rentals

A sunset over a coastal landscape with a small island surrounded by water.

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Our top choices for Stock Island hotels

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

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.

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

1. The Perry Hotel & Marina Key West

Stock Island

Jade

3.029.133 ₫

4.996.527 ₫ total

includes taxes & fees

26 Oct - 27 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 breakfast setting with a table, chairs, a vase with flowers, and a city view.

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

2. Hilton Key West Resort & Marina

Stock Island

Molly

3.281.638 ₫

5.212.082 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

Three floating cabins with balconies, named Aqua-Lodge, docked on calm water with a clear sky and trees in the background.

A wooden dock with a table and chairs, a table lamp, and a toaster.

A wooden deck with a table and chairs, overlooking a calm water body with boats and a house in the background.

3. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

2.549.325 ₫

7.310.103 ₫ total

includes taxes & fees

9 Oct - 10 Oct

A beachside resort with a wooden deck, palm trees, and a sunset view.

A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.

A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

4. Grand Marina Suite by Brightwild Waterfront

Stock Island

Pawel

10.301.527 ₫

17.905.760 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

5. Havana Cabana at Key West

New Town

Stephanie

3.483.196 ₫

5.566.096 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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.

6. Blue Flamingo Resort Key West

New Town

Esteban

3.071.191 ₫

4.917.252 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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 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.

7. Hampton Inn Key West FL

Key West

Jaycie

4.392.986 ₫

4.942.109 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

Nancy

3.201.598 ₫

4.478.859 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

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

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

9. 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

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.

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.

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

New Town

Brian

3.353.226 ₫

4.503.330 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

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

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.

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

A beach with palm trees, lounge chairs, and umbrellas.

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

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

12. Parrot Key Hotel & Villas

Northside Resort

Anthony

3.222.388 ₫

5.116.321 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

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

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

A modern dining area with a glass table, four chairs, and a ceiling fan.

13. Beachside Resort & Residences

Key West

James

2.269.031 ₫

5.038.335 ₫ total

includes taxes & fees

7 Oct - 8 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.

14. Margaritaville Beach House Key West

Key West

TRICIA LYNN

5.431.283 ₫

7.750.006 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

15. Hilton Garden Inn Key West / The Keys Collection

New Town

Walt

2.866.626 ₫

3.955.968 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

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

16. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Darlene

5.721.038 ₫

8.190.290 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. Hyatt Centric Key West Resort and Spa

Key West Historic District

yendy

5.743.127 ₫

8.273.611 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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 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.

18. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

5.016.271 ₫

5.643.305 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A pool area with lounge chairs and a cabana.

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

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

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

19. 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

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

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.

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

20. Artist House Key West

Key West Historic District

NATHAN

4.276.940 ₫

4.811.752 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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Where to stay in Stock Island

Find the best Stock Island areas for the activities you enjoy most.

A large red brick building with arched windows and a prominent entrance.

A lighthouse, a white building with green shutters, and a small white structure with a wooden roof.

A white lighthouse with a black top, a white building with green shutters, and a palm tree.

A white lighthouse, a white building with green shutters, and a white picket fence.

A white lighthouse with a black top, surrounded by lush green trees and a white picket fence.

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

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The Monroe County Courthouse with a clock tower, surrounded by trees and a clear blue sky.

A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

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

A historic building with ornate architecture, a balcony, and a coat of arms.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

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A white lighthouse surrounded by lush greenery and a white picket fence.

A wooden sign for Ernest Hemingway Home with admission prices and operating hours.

A white lighthouse with a black top, surrounded by lush green trees and a clear blue sky.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.

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A row of pastel-colored houses with white railings and a clear blue sky.

A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

A white church with a bell tower and a large arched entrance.

A historic street with ornate buildings, including a church with twin spires and a building with a balcony.

A person skydiving over a coastal landscape with clear turquoise waters, green vegetation, and a road.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Fort East Martello Museum and Gallery.

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A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

A vintage red bus with 'Old Town Trolley Tours' written on it, parked on a paved area with people around.

A large sculpture with text indicating it is the Southernmost Point of the Continental U.S.A. and 90 miles to Cuba.

A colorful marker labeled 'Southernmost Point' in Key West, FL, with a view of the ocean in the background.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

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Stay near popular Stock Island attractions

A serene landscape with a pond, palm trees, and a golf course.

Key West Golf Club

8.4/10 (163 reviews)

America's only Caribbean-style golf course features tropical landscapes and the infamous "Mangrove Hole" requiring a shot over dense mangroves. Enjoy the Rees Jones design amid palm-lined fairways.

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A stone pathway through a tropical forest with dense foliage and a stone wall.

Key West Tropical Forest and Botanical Garden

8.0/10 (9 reviews)

Enjoy the beautiful sunsets and explore Key West Tropical Forest and Botanical Garden, a lovely green space in Key West. Stroll along the area's seaside or experience its lively festivals.

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Florida Keys Community College Library

After visiting Florida Keys Community College Library, make a plan to see the other sights and activities in Key West.

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Tennesse Williams Fine Art Center

You can get tickets for a performance at Tennesse Williams Fine Art Center during your trip to Key West.

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Learn more about Stock Island

Just a stone's throw from Key West, this laid-back island offers a glimpse into authentic Florida Keys life. Explore colourful marinas, savour fresh seafood at local docks, and join fishing charters for a chance to reel in the big one.

See all hotels in Stock Island

Top Stock Island Hotel Reviews

Parrot Key Hotel & Villas

10/10 Excellent

"Great place definitely staying there next time"

Blue Flamingo Resort Key West

10/10 Excellent

"Hot water in showers, bed comfort was okay, food was decent at the bars/restaurants, staff was friendly, pool clean and open until 11pm. Lots of fun games to play outside. The property and rooms were clean and the shuttle service to town was easy and very helpful!"

Margaritaville Beach House Key West

10/10 Excellent

"The staff were friendly and extremely helpful. The shuttle provided an excellent means for transportation to Duval Street as well as the ferry. The beaches in Key West are not the greatest so if your decision is based on proximity to the beach, it may not be worthwhile. The pool at the resort was awesome and the pool/bar/restaurant service really made this tropical destination pop!"

Pier House Resort & Spa

10/10 Excellent

"Love pier house resort"

Havana Cabana at Key West

10/10 Excellent

"This was my first stay here and I would certainly return. There was heavy rain during my stay which forced some changing of plans and they apparently had some leaking issues which forced me to change rooms, and the room was not anywhere near as nice. I was upset about that, but they compensated me very fairly, and it was mother nature‘s fault, not theirs. The pool is great, the pool bar and area is great, the food truck food was very good and the shuttle taking you into town on a regular basis was perfect."

The Southernmost Inn - Adults Only

10/10 Excellent

"This place was great quiet and close to everything"

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"Clear room, great views"

The Perry Hotel & Marina Key West

10/10 Excellent

"The whole experience was fantastic. I wouldn't stay anywhere else!"

Hilton Key West Resort & Marina

10/10 Excellent

"This was our second time to stay here and this place never disappoints. Staff is wonderful too"

More cheap stays in Stock Island

Alexander Palms Court

715 South St Key West FL

3.098.950 ₫

3.486.416 ₫ total

7 Oct - 8 Oct

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

3.309.576 ₫

4.561.614 ₫ total

7 Oct - 8 Oct

includes taxes & fees

Pegasus International Hotel

501 Southard Street Key West FL

3.071.191 ₫

4.771.036 ₫ total

7 Oct - 8 Oct

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

4.392.986 ₫

4.942.109 ₫ total

7 Oct - 8 Oct

includes taxes & fees

9/10 Wonderful! (1,547 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

3.613.166 ₫

4.942.110 ₫ total

7 Oct - 8 Oct

includes taxes & fees

8.6/10 Excellent! (1,386 reviews)

Tranquility Guest House

302 Angela st Key West FL

3.285.069 ₫

6.005.299 ₫ total

13 Oct - 14 Oct

includes taxes & fees

9/10 Wonderful! (33 reviews)

Hotels in Stock Island with star rating

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Find hotels in Stock Island, FL from 3.486.416 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Stock Island

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Stock Island hotels

1. The Perry Hotel & Marina Key West

2. Hilton Key West Resort & Marina

3. Aqua Lodges at Hurricane Hole Marina

4. Grand Marina Suite by Brightwild Waterfront

5. Havana Cabana at Key West

6. Blue Flamingo Resort Key West

7. Hampton Inn Key West FL

8. DoubleTree Resort by Hilton Grand Key - Key West

9. Hyatt Vacation Club at Windward Pointe, Key West

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

11. Hyatt Vacation Club at Beach House, Key West

12. Parrot Key Hotel & Villas

13. Beachside Resort & Residences

14. Margaritaville Beach House Key West

15. Hilton Garden Inn Key West / The Keys Collection

16. The Reach Key West, Curio Collection by Hilton

17. Hyatt Centric Key West Resort and Spa

18. Courtyard by Marriott Key West Waterfront

19. Ocean Key Resort - A Noble House Resort

20. Artist House Key West

Where to stay in Stock Island

Old Town Key West

Downtown Key West

Key West Historic District

New Town

Uptown - Upper Duval

Stay near popular Stock Island attractions

Key West Golf Club

Key West Tropical Forest and Botanical Garden

Florida Keys Community College Library

Tennesse Williams Fine Art Center

Learn more about Stock Island

Top Stock Island Hotel Reviews

Parrot Key Hotel & Villas

Blue Flamingo Resort Key West

Margaritaville Beach House Key West

Pier House Resort & Spa

Havana Cabana at Key West

The Southernmost Inn - Adults Only

Casa Marina Key West, Curio Collection by Hilton

The Perry Hotel & Marina Key West

Hilton Key West Resort & Marina

More cheap stays in Stock Island

Alexander Palms Court

Ibis Bay Beach Resort

Pegasus International Hotel

Hampton Inn Key West FL

Southwinds Motel

Tranquility Guest House

Hotels in Stock Island with star rating

Explore a world of travel with Expedia

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