Book Holiday Homes in Raccoon Key

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Featured Holiday Homes in Raccoon Key

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Stock Island
When you stay at this vacation home in Key West, you'll be on the waterfront, a 3-minute drive from Key West Golf Club and 8 minutes from Smathers Beach.
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

Key West
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 4 minutes by foot from Florida Keys Beaches.
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Stock Island
When you stay at this vacation home in Key West, you'll be on the waterfront, a 3-minute drive from Key West Golf Club and 8 minutes from Smathers Beach.
INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!
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OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!

Key West
When you stay at this vacation home in Key West, you'll be by the sea, a 3-minute drive from Key West Golf Club and 10 minutes from Duval Street.
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool

Key West
With a stay at this vacation home, you'll be centrally located in Key West, just a 3-minute walk from Duval Street and 11 minutes by foot from Ernest Hemingway ...
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!

Key West
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 4 minutes by foot from Ernest Hemingway Home and ...
EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!

Key West
With a stay at this vacation home, you'll be centrally located in Key West, just a 5-minute walk from Duval Street and 8 minutes by foot from Ernest Hemingway ...
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
Poolside Cottage #411

Poolside Cottage #411

Key West
The price is AU$847 per night from 8 Jan to 9 Jan
AU$847
includes taxes & fees
8 Jan - 9 Jan 2025
When you stay at this vacation home in Key West, you'll be by the sea, within a 5-minute drive of Smathers Beach and Florida Keys Beaches.
Poolside Cottage #411
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

Key West
With a stay at this vacation home in Key West (Northside Resort), you'll be a 4-minute drive from Florida Keys Beaches and 5 minutes from Duval Street.
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Raccoon Key Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Raccoon Key vacation homes are the perfect way for you to wing it.

Holiday houses in Raccoon Key let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Raccoon Key in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Raccoon Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Raccoon Key with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Raccoon Key vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Raccoon Key Holiday Homes essential information

Accommodation
729 Holiday Homes
Lowest Price
AU$469
Highest Price
AU$847
Popular accommodation
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!, SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!, OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!, LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool, EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!, ~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!, Poolside Cottage #411, Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!

Top trending hotels in Raccoon Key

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$612 per night from 8 Jan to 9 Jan
AU$612
includes taxes & fees
8 Jan - 9 Jan 2025
When you stay at Oceans Edge Key West Resort, Hotel & Marina in Key West, you'll be next to a golf course, a 5-minute drive from Key West Golf Club and 10 minutes ...
Oceans Edge Key West Resort, Hotel & Marina
Southernmost Beach Resort

Southernmost Beach Resort

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is AU$751 per night from 14 Jan to 15 Jan
AU$751
includes taxes & fees
14 Jan - 15 Jan 2025
With a stay at Southernmost Beach Resort, you'll be centrally located in Key West, steps from South Beach and within a 5-minute walk of Southernmost Point.
Southernmost Beach Resort
Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL
The price is AU$520 per night from 23 Dec to 24 Dec
AU$520
includes taxes & fees
23 Dec - 24 Dec
With a stay at Havana Cabana at Key West - Adults Only in Key West (New Town), you'll be a 5-minute drive from Florida Keys Beaches and 6 minutes from Duval ...
Havana Cabana at Key West - Adults Only
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Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$469 per night from 12 Jan to 13 Jan
AU$469
includes taxes & fees
12 Jan - 13 Jan 2025
When you stay at Beachside Resort & Residences in Key West, you'll be next to a golf course, within a 5-minute drive of Key West Golf Club and Smathers ...
Beachside Resort & Residences
Don't see what you're looking for?
See all available properties in Raccoon Key
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.