Book Holiday Homes in Raccoon Key

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Featured Holiday Homes in Raccoon Key

Tropical Key West out of the way

Tropical Key West out of the way

Key West
With a stay at this vacation home in Key West, you'll be within a 10-minute drive of Smathers Beach and Florida Keys Beaches.
Opens in a new windowTropical Key West out of the way
The Hemingway Caribbean Townhome & Private Pool Near Beach in charming Key West

The Hemingway Caribbean Townhome & Private Pool Near Beach in charming Key West

Key West, FL
With a stay at Hemingway Caribbean Townhome/Private Pool by Beach,Key West charm,free parking in Key West (Old Town Key West), you'll be a 4-minute walk from ...
Opens in a new windowThe Hemingway Caribbean Townhome & Private Pool Near Beach in charming Key West
Perfect Location, 
Private Heated Pool,
Pristine Luxury Home!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Key West
The price is AU$2,930 per night from 16 Nov to 17 Nov
AU$2,930
16 Nov - 17 Nov
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 3 minutes by foot from Ernest Hemingway Home and ...
Opens in a new windowPerfect Location, Private Heated Pool, Pristine Luxury Home!
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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 9 minutes by foot from Ernest Hemingway ...
Opens in a new windowLOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cudjoe
With a stay at this vacation home in Summerland Key, you'll be near the beach, within a 10-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowOceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK

Key West
The price is AU$1,041 per night from 18 Nov to 19 Nov
AU$1,041
18 Nov - 19 Nov
includes taxes & fees
With a stay at this vacation home in Key West (Old Town Key West), you'll be steps from Duval Street and 3 minutes by foot from Ernest Hemingway Home and ...
Opens in a new windowSpacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 15-minute drive of Florida Keys Beaches and Venture Out Keys.
Opens in a new windowCOCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!

Key West
With a stay at this vacation home, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from South Beach.
Opens in a new windowKATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Key
With a stay at this vacation home in Summerland Key, you'll be on the waterfront, within a 10-minute drive of Florida Keys Beaches and Upper Sugarloaf Key.
Opens in a new windowCudjoe Cottages, swimming pool, just 20 miles from Key West
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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
823 Holiday Homes
Lowest Price
AU$246
Highest Price
AU$2,930
Popular accommodation
Tropical Key West out of the way , The Hemingway Caribbean Townhome & Private Pool Near Beach in charming Key West, Perfect Location, Private Heated Pool, Pristine Luxury Home!, LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK, COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!, KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!, Cudjoe Cottages, swimming pool, just 20 miles from Key West

Top trending hotels in Raccoon Key

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$291 per night from 19 Nov to 20 Nov
AU$291
19 Nov - 20 Nov
includes taxes & fees
When you stay at Beachside Resort & Residences in Key West, you'll be next to a golf course, a 5-minute drive from Smathers Beach and 8 minutes from Duval ...
Opens in a new windowBeachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 17 Nov to 18 Nov
AU$246
17 Nov - 18 Nov
includes taxes & fees
A stay at Blue Flamingo Resort Key West places you in the heart of Key West, within a 10-minute drive of Stock Island Yacht Club & Marina and Key West Lighthouse ...
Opens in a new windowBlue Flamingo Resort Key West
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$367 per night from 16 Nov to 17 Nov
AU$367
16 Nov - 17 Nov
includes taxes & fees
When you stay at Oceans Edge Key West Resort, Hotel & Marina in Key West, you'll be next to a golf course, within a 15-minute drive of Duval Street and Smathers ...
Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Save an average of 15% on thousands of hotels when you're signed in
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is AU$416 per night from 30 Nov to 1 Dec
AU$416
30 Nov - 1 Dec
includes taxes & fees
With a stay at Southernmost Beach Resort and Guesthouses, you'll be centrally located in Key West, steps from South Beach and within a 5-minute walk of Southernmost ...
Opens in a new windowSouthernmost Beach Resort and Guesthouses
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.