Raccoon Key Holiday Rentals, Key West: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Raccoon Key

Pet friendly

Apartment

Apart hotel

Pool

Condo

Spa

Hot tub

Family friendly

Cottage

Resort

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Raccoon Key hotels

Reserve now, pay later

Hotel

Breakfast included

Aparthotel

Indoor fireplace

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

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.

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and a ceiling fan.

1. Capmar House by Brightwild Huge Home Pool

Raccoon Key

Karen

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

25 Aug - 26 Aug

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.

2. Floralee House in Key West

Raccoon Key

26.758.291 ₫

54.782.697 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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 bedroom with a bed, nightstands, a ceiling fan, and large windows with curtains.

A modern hotel room with a large bed, a seating area, a desk, and a view of the water.

3. Waterfront Luxury Home - Tidelands House

Raccoon Key

40.151.430 ₫

71.495.286 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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 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.

4. Springtide House by Brightwild Waterfront Pool

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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

A modern bathroom with a large mirror, two sinks, a toilet, and a glass-enclosed shower.

5. Parking Pool Dock - Shellstone House

Raccoon Key

40.151.430 ₫

71.495.286 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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.

6. Aquaria House by Brightwild Pool Boat Dock

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

3 Sept - 4 Sept

A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

A two-story house with a swimming pool, a covered patio, and a staircase leading to the upper floor.

A staircase with white railings and beige steps leading to a landing.

A spacious living area with a dining table and chairs, a staircase with white railings, and a view of the outdoors.

7. Mastway House by Brightwild Pool Dock

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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 kitchen with a central island, bar stools, pendant lights, and a built-in TV.

8. Brand New The Greenmoor House With Pool

Raccoon Key

33.454.963 ₫

63.961.761 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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

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

A two-story house with a swimming pool, white railings, and a covered patio area.

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

9. Waterlane House by Brightwild Pool Boat Dock

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

1 Sept - 2 Sept

A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

A rectangular swimming pool with clear blue water, surrounded by a paved deck. There are lounge chairs and a small table on the deck. Palm trees and a grassy area are visible in the background.

A spacious living area with a dining table and chairs, a kitchen with white cabinets, and a large window overlooking a scenic view.

A spacious living room with a large TV, blue sofas, and a wooden coffee table.

10. Suncoast House by Brightwild Pool Boat Dock

Raccoon Key

20.061.824 ₫

45.110.272 ₫ total

includes taxes & fees

30 Aug - 31 Aug

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

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

A two-story house with a front porch, a driveway, and palm trees.

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

11. Mirador House by Brightwild Pool Dock

Raccoon Key

20.061.824 ₫

45.110.272 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and a view to the outside.

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

A spacious kitchen with white cabinets, a central island, and a dining area with chairs.

12. Evershore House Pool Parking Dock

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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 spacious room with a long wooden table, comfortable seating, a large window with a view of greenery, and a modern light fixture.

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

13. The Fairhaven House at Solaire Lunara Bay

Raccoon Key

40.151.430 ₫

71.495.286 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

A modern bathroom with a glass-enclosed shower, a white sink with black fixtures, and a large mirror.

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

14. Palmgale House in Key West

Raccoon Key

26.758.291 ₫

54.782.697 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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, surrounded by lush greenery and a fenced yard.

A spacious kitchen with a large island, white cabinetry, and a view of the outdoors.

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

15. Spindrift House by Brightwild Huge Pool Dock

Raccoon Key

20.061.824 ₫

40.667.940 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

A modern bedroom with a large bed, a desk, a ceiling fan, and a window with curtains.

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

16. New Waterfront Home - Sunray House

Raccoon Key

40.458.471 ₫

71.840.708 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

A modern kitchen with white cabinetry, a central island, and a black and white backsplash.

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

17. Ebberly House by Brightwild Amazing Pool

Raccoon Key

26.758.291 ₫

54.782.697 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

A spacious dining area with a long wooden table, six chairs, and pendant lights.

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

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

18. Brand New Build Larkshine House - Pool

Raccoon Key

40.151.430 ₫

69.849.978 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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 dining area with a sofa and chairs.

A modern kitchen with white cabinetry, a central island, and pendant lighting.

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

19. New Windrose House by Brightwild Pool

Raccoon Key

26.758.291 ₫

54.782.697 ₫ total

includes taxes & fees

24 Aug - 25 Aug

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

A modern kitchen with white cabinetry, a large island, pendant lighting, and a view of greenery outside.

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, outdoor seating, and a covered patio.

20. New Crestwood House by Brightwild Huge Pool

Raccoon Key

26.758.291 ₫

54.782.697 ₫ total

includes taxes & fees

24 Aug - 25 Aug

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Raccoon Key

Find the best Raccoon Key areas for the activities you enjoy most.

A white lighthouse with a small adjacent building, surrounded by lush green trees and a clear blue sky.

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

A beach with people sunbathing, palm trees, and a multi-story building in the background.

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

A street lined with colorful historic buildings, a clear blue sky, and a motorcyclist riding down the road.

Old Town Key West

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

See properties

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

See properties

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.

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

Downtown Key West

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

See properties

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

A red brick building with arched windows and a tall chimney.

A cozy library with wooden furniture, bookshelves, and a deer head on the wall.

A red brick building with arched windows and a signboard.

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.

See properties

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 Key West Tropical Forest and Botanical Garden.

See properties

Top Raccoon Key Hotel Reviews

Hampton Inn Key West FL

10/10 Excellent

"Everything was good during our stay. Only problem we had to ask for clean towels once during our stay. The shuttle service to Old Town was a great feature."

Beachside Resort & Residences

10/10 Excellent

"The room was excellent. The staffs was so nice and didn't have no problem getting you bag of ice at any time. The breakfast bar wasnt open because its still getting work on. But an all it was nice an we had a great time. Thank you"

The Reach Key West, Curio Collection by Hilton

10/10 Excellent

"Great place. Great atmosphere. Very friendly and helpful staff. Great location. Great food. I’ll be back."

Ibis Bay Beach Resort

10/10 Excellent

"I always stay here. It's nice and clean. Rooms are pretty tight, but they are nice."

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Buen lugar y relación precio calidad Habitación con olor a humedad"

Parrot Key Hotel & Villas

10/10 Excellent

"Great stay"

Pier House Resort & Spa

10/10 Excellent

"Great location and staff!"

Margaritaville Beach House Key West

8/10 Good

"Stay was really nice . Hotel front staff very friendly and helpful. Hotel transportation was a plus . Pool was nice . Key card for room great idea to wear as a wristband. Food was good at hotel restaurant. Service was slow , it was overall a very nice experience. Beach avoid due to seaweed issues ; may want to check on timing . Seaweed is a big issue."

Southwinds Motel

10/10 Excellent

"This was day 16 of a US road trip and this was BY FAR my favorite stay. 1 block away from Duval St. Free drink tickets. Great bed and pillows. Microwave, fridge. Everything was GREAT! Only downside was we went to bed at 10 and the nearby bar was still playing loud live music, however the loud AC unit drowned it out lol. Ice machine could use something to make it look cleaner/better, but still produced ice just fine. Breakfast was pretty much entirely bread/muffins/cereal/bagels. Parking was not free, which is also a bummer. But being so close to everything we wanted made up for it."