Book Holiday Homes in Fleming Key

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Featured Holiday Homes in Fleming Key

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 South Beach.
Opens in a new windowSUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!
DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!

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 6 minutes by foot from Ernest Hemingway ...
Opens in a new windowDELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

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 South Beach.
Opens in a new windowLADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!
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CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

Key West
With a stay at this vacation home, you'll be centrally located in Key West, within a 5-minute drive of Duval Street and Ernest Hemingway Home and Museum.
Opens in a new windowCONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!
 Sept.mid wk.spec.117. lod +
10 min walk beach, close to all +
full kitch& patio

Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

Key West
The price is AU$508 per night from 27 Oct to 28 Oct
AU$508
27 Oct - 28 Oct
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Key West, within a 5-minute drive of Duval Street and Ernest Hemingway Home and Museum.
Opens in a new window Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio
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, within a 10-minute drive of Smathers Beach and Florida Keys Beaches.
Opens in a new windowONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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!
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!

Key West
With a stay at this vacation home in Key West (Old Town Key West), you'll be a 2-minute walk from Duval Street and 7 minutes by foot from South Beach.
Opens in a new windowA KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!
3-Story spacious conch style home w/ private pool & dock!

3-Story spacious conch style home w/ private pool & dock!

Key West
With a stay at this vacation home in Key West (Meadows), you'll be within a 5-minute drive of Duval Street and Ernest Hemingway Home and Museum.
Opens in a new window3-Story spacious conch style home w/ private pool & dock!
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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.

Fleming 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 Fleming Key vacation homes are the perfect way for you to wing it.

Holiday houses in Fleming 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 Fleming 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 Fleming Key adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Fleming 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 Fleming 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.

Fleming Key Holiday Homes essential information

Accommodation
763 Holiday Homes
Lowest Price
AU$240
Highest Price
AU$508
Popular accommodation
SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!, DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!, LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!, CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!, Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio, ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!, KATE'S KRAWL OFF DUVAL ~ 1 BR/1 BA Private Home/Outdoor Deck/Steps to Duval!, A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town /Private Heated Pool!, 3-Story spacious conch style home w/ private pool & dock!

Top trending hotels in Fleming Key

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
The price is AU$404 per night from 13 Oct to 14 Oct
AU$404
13 Oct - 14 Oct
includes taxes & fees
Located in Key West, Margaritaville Beach House Key West is by the ocean, within a 5-minute drive of Smathers Beach and Fort East Martello Museum and ...
Opens in a new windowMargaritaville Beach House 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$412 per night from 30 Sept to 1 Oct
AU$412
30 Sept - 1 Oct
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
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$395 per night from 29 Oct to 30 Oct
AU$395
29 Oct - 30 Oct
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
Save an average of 15% on thousands of hotels when you're signed in
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$240 per night from 29 Sept to 30 Sept
AU$240
29 Sept - 30 Sept
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
Don't see what you're looking for?
See all available properties in Fleming 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.