Raccoon Key Holiday Rentals, Key West: Private House Rentals

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Our top choices for Raccoon Key hotels

A white two-story house with a balcony and a swimming pool.

A spacious kitchen with wooden cabinets, a large island, and modern appliances.

A balcony with a view of a swimming pool, palm trees, and a fenced yard.

A residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.

1. Capmar House by Brightwild Huge Home Pool

Raccoon Key

Karen

฿27,137

฿55,010 total

includes taxes & fees

12 Oct - 13 Oct

A poolside area with lounge chairs, a wooden table, and palm trees.

A patio with white wicker furniture, palm trees, and a view of a lake.

A modern living room with a sectional sofa, a coffee table, and a view of the outdoor patio area.

A large, modern resort with multiple buildings, a central pool, and a marina.

2. The Fairhaven House at Solaire Lunara Bay

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, pendant lighting, and large windows offering a view of the outdoors.

A boat with people jumping into the water.

A modern bedroom with a large bed, bedside tables, a ceiling fan, and a view of a lake.

A modern living room with a sectional sofa, a dining area with a large table, and a TV mounted on the wall.

3. Parking Pool Dock - Shellstone House

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

12 Oct - 13 Oct

A spacious living room with a large dining table, comfortable seating, and large windows offering a view of the outdoors.

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

A two-story building with a symmetrical facade, a central entrance, and a staircase leading to the main entrance.

A modern living room with a white coffee table, a TV on the wall, and a dining area with wooden chairs and a black table.

4. Waterfront Luxury Home - Tidelands House

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, wooden cabinets, a built-in oven, and a large window providing natural light.

A large white house with a swimming pool, outdoor seating, and a covered patio area.

A large white house with a pool, outdoor seating area, and a hammock.

A modern living room with a green sofa, two round white coffee tables, and a dining area with a table and chairs.

5. Brand New The Greenmoor House With Pool

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a large island, bar stools, and pendant lighting.

A modern kitchen with a central island, pendant lighting, and a view of the outdoors.

A large, multi-story white house with a swimming pool, surrounded by lush greenery and palm trees.

A spacious living area with a large dining table, comfortable seating, a wicker chandelier, and a view of palm trees through large windows.

6. The Joyrise House at Solaire Lunara Bay

Raccoon Key

฿54,312

฿96,710 total

includes taxes & fees

12 Oct - 13 Oct

A modern house with a swimming pool, outdoor seating, and palm trees.

A modern kitchen with a central island, bar stools, pendant lights, and a staircase leading to another room.

A covered outdoor seating area with white chairs and a ceiling fan, overlooking a swimming pool and a well-maintained lawn.

A spacious living area with a light blue sofa, a round coffee table, and a dining area with wooden chairs and a table.

7. Floralee House in Key West

Raccoon Key

฿36,195

฿74,103 total

includes taxes & fees

12 Oct - 13 Oct

A spacious kitchen with a marble island, pendant lighting, and a dining area with chairs and a table.

A modern living room with a sofa, coffee table, and a chessboard. There is a kitchen in the background with a stove, microwave, and cabinets.

A two-story house with a pool, surrounded by a well-maintained lawn and palm trees.

A two-story house with a pool, outdoor seating, and a covered patio.

8. New Crestwood House by Brightwild Huge Pool

Raccoon Key

฿36,195

฿74,103 total

includes taxes & fees

12 Oct - 13 Oct

A white two-story house with a central archway and a paved driveway.

A hotel room with a large bed, a ceiling fan, a window with curtains, a bedside table with a lamp, and a patterned wall.

A modern house with a swimming pool, lounge chairs, and a covered patio area.

9. Palmgale House in Key West

Raccoon Key

฿36,195

฿74,103 total

includes taxes & fees

12 Oct - 13 Oct

A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

A modern living room with a sofa, two armchairs, a coffee table, and a dining area with a table and chairs.

A modern kitchen with a central island, bar stools, pendant lighting, and a large window providing natural light.

A modern resort with a well-maintained lawn, outdoor seating area, and a large building with multiple floors.

10. New Waterfront Home - Dreamside House

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a central island, bar stools, and a large window.

A modern living space with a large wooden dining table, a sofa set, and a kitchen area.

A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.

A modern two-story house with a paved driveway and a well-maintained lawn.

11. Brand New Catchlight House With Private Pool

Raccoon Key

฿37,018

฿75,028 total

includes taxes & fees

15 Oct - 16 Oct

A living room with two sofas, a coffee table, and a view of the outdoors.

A person performing a yoga pose on a mat in a room with a wooden floor and a mirror on the wall.

A two-story house with a front porch, a double door, and a number '8' on the door.

A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view of the outdoors through large windows.

12. Waterlane House by Brightwild Pool Boat Dock

Raccoon Key

฿27,137

฿55,010 total

includes taxes & fees

12 Oct - 13 Oct

A two-story house with a pool, surrounded by palm trees and a clear sky.

A covered outdoor area with a pool, white furniture, and ceiling fans.

A modern living room with a sofa, coffee table, and a rug. There is a kitchen area with a bar and seating.

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

13. Mirador House by Brightwild Pool Dock

Raccoon Key

฿27,137

฿61,019 total

includes taxes & fees

15 Oct - 16 Oct

A modern kitchen with a central island, bar stools, a large TV, and a built-in oven.

A spacious living area with a large dining table, white sofas, and a TV mounted on the wall.

A two-story white house with a swimming pool, outdoor seating area, and a well-maintained lawn.

14. Brand New Build Larkshine House - Pool

Raccoon Key

฿45,253

฿84,293 total

includes taxes & fees

12 Oct - 13 Oct

A modern kitchen with a large island, bar stools, and a view of the outdoors.

A two-story building with a symmetrical facade, a central entrance, and a car parked in front.

A modern hotel bedroom with a large bed, two bedside tables, a ceiling fan, and a view of the water.

A modern living room with a large dining table, sofas, and a view of a body of water through large windows.

15. New Waterfront Home - Sunray House

Raccoon Key

฿45,253

฿86,519 total

includes taxes & fees

13 Oct - 14 Oct

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

A two-story house with a swimming pool, outdoor seating, and a fenced yard.

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

A spacious interior with a wooden staircase, a modern light fixture, and a view of the outdoors.

16. Spindrift House by Brightwild Huge Pool Dock

Raccoon Key

฿27,137

฿55,010 total

includes taxes & fees

18 Oct - 19 Oct

A modern living room with a dark blue sectional sofa, a wooden coffee table, and a kitchen area with a blue backsplash and white cabinets.

A modern kitchen with a large island, pendant lighting, and a backsplash with blue tiles.

A bedroom with a large bed, a balcony with a view, and a door leading to another room.

A modern outdoor pool area with lounge chairs and umbrellas, surrounded by a well-maintained lawn and palm trees.

17. Ebberly House by Brightwild Amazing Pool

Raccoon Key

฿36,195

฿74,103 total

includes taxes & fees

15 Oct - 16 Oct

A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.

A covered outdoor area with a pool, white furniture, and a view of a lake.

A two-story house with a swimming pool, outdoor seating, and a covered patio.

A modern kitchen with a sliding glass door leading to a balcony, a dining area with a gray sofa, and a small island with a vase of white flowers.

18. Springtide House by Brightwild Waterfront Pool

Raccoon Key

฿27,137

฿55,010 total

includes taxes & fees

21 Oct - 22 Oct

A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.

A modern kitchen with a central island, bar stools, pendant lights, and a view of the outdoors.

A two-story house with a swimming pool, outdoor seating, and a barbecue area.

A modern kitchen with a central island, bar stools, pendant lights, and a dining area with a sofa and chairs.

19. New Windrose House by Brightwild Pool

Raccoon Key

฿36,195

฿74,103 total

includes taxes & fees

18 Oct - 19 Oct

A spacious kitchen with a large island, white cabinetry, and pendant lighting.

A spacious living room with a large flat-screen TV, comfortable seating, a coffee table, and a sliding glass door leading to an outdoor patio.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with seating.

A pool area with a covered deck, palm trees, and a house with a balcony.

20. Aquaria House by Brightwild Pool Boat Dock

Raccoon Key

฿27,137

฿55,010 total

includes taxes & fees

11 Nov - 12 Nov

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Where to stay in Raccoon Key

Find the best Raccoon Key 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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A sunset over a coastal landscape with a small island surrounded by water.

A coastal cityscape with a golf course and marina.

A marina with boats docked, a clear blue sky, and buildings in the background.

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

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

Stock Island

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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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Top Raccoon Key Hotel Reviews

Opal Key Resort & Marina, Key West

10/10 Excellent

"Great location. Walking distance to Anything you’d want to do in Key West. Housekeeping staff very attentive. Valets very friendly and quick to attend. Room was clean spacious and bed comfortable. Restaurant was just OK. Staff there not as friendly and attentive. Pool was ok."

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

10/10 Excellent

"Very pleasant stay"

The Southernmost Inn - Adults Only

10/10 Excellent

"We had a great stay. The staff was amazing. Rooms were clean and we enjoyed the wine and cheese from 5-7 daily."

Havana Cabana at Key West

10/10 Excellent

"This resort is AMAZING!!!! If you don't want to, you never have the leave the resort, as EVERYTHING IS THERE!!! The Mojito Bar is awesome, food is great!!! Bartender Lana at the Mojito Bar is THE BEST!!! THE ENTIRE STAFF IS AMAZING!!! GOING BACK, I THINK IN FEW WEEKS, AGAIN!!!!"

Parrot Key Hotel & Villas

8/10 Good

"Staff was very helpful, check in and out was very easy. The rooms could use some updates with new carpet and window seals that had visible water damage."

Hampton Inn Key West FL

10/10 Excellent

"Very good sleeping bed and an excellent view to the ocean. But the air conditioner and refrigerator were very noisy"

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent

"We had a wonderful stay at casa marina. The rooms were clean, staff were super friendly and always so helpful, the entire resort felt like a dream. We can’t wait to be back!"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"The rooms were nice. The staff were friendly, but the back yard lounge/pool area was my favourite. Beautiful place to longe day or night. The free shuttle to Duval street runs every hour and made it so easy to enjoy downtown!"

The Perry Hotel & Marina Key West

10/10 Excellent

"Súper bueno todo"

More cheap stays in Raccoon Key

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿3,839

฿5,400 total

12 Oct - 13 Oct

includes taxes & fees

Pegasus International Hotel

501 Southard Street Key West FL

฿3,819

฿5,994 total

12 Oct - 13 Oct

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,331

฿5,998 total

13 Oct - 14 Oct

includes taxes & fees

9/10 Wonderful! (1,555 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

฿4,521

฿6,218 total

26 Oct - 27 Oct

includes taxes & fees

8.6/10 Excellent! (1,383 reviews)

Alexander Palms Court

715 South St Key West FL

฿5,703

฿6,417 total

12 Oct - 13 Oct

includes taxes & fees

9.4/10 Exceptional! (1,001 reviews)

Tranquility Guest House

302 Angela st Key West FL

฿4,396

฿7,926 total

14 Oct - 15 Oct

includes taxes & fees

9/10 Wonderful! (35 reviews)

Explore a world of travel with Expedia

More ways to book

Book Hotels in Raccoon Key on Expedia.com

Find hotels in Raccoon Key, FL from ฿5,400

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Raccoon Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Raccoon Key hotels

1. Capmar House by Brightwild Huge Home Pool

2. The Fairhaven House at Solaire Lunara Bay

3. Parking Pool Dock - Shellstone House

4. Waterfront Luxury Home - Tidelands House

5. Brand New The Greenmoor House With Pool

6. The Joyrise House at Solaire Lunara Bay

7. Floralee House in Key West

8. New Crestwood House by Brightwild Huge Pool

9. Palmgale House in Key West

10. New Waterfront Home - Dreamside House

11. Brand New Catchlight House With Private Pool

12. Waterlane House by Brightwild Pool Boat Dock

13. Mirador House by Brightwild Pool Dock

14. Brand New Build Larkshine House - Pool

15. New Waterfront Home - Sunray House

16. Spindrift House by Brightwild Huge Pool Dock

17. Ebberly House by Brightwild Amazing Pool

18. Springtide House by Brightwild Waterfront Pool

19. New Windrose House by Brightwild Pool

20. Aquaria House by Brightwild Pool Boat Dock

Where to stay in Raccoon Key

Old Town Key West

Stock Island

Downtown Key West

Key West Historic District

New Town

Top Raccoon Key Hotel Reviews

Opal Key Resort & Marina, Key West

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

The Southernmost Inn - Adults Only

Havana Cabana at Key West

Parrot Key Hotel & Villas

Hampton Inn Key West FL

Casa Marina Key West, Curio Collection by Hilton

DoubleTree Resort by Hilton Grand Key - Key West

The Perry Hotel & Marina Key West

More cheap stays in Raccoon Key

Ibis Bay Beach Resort

Pegasus International Hotel

Hampton Inn Key West FL

Southwinds Motel

Alexander Palms Court

Tranquility Guest House

Explore a world of travel with Expedia

Go further with the Expedia app