Book Holiday Homes in Duck Key

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Featured Holiday Homes in Duck Key

The Hammocks at Marathon

The Hammocks at Marathon

2.5 out of 5
1688 Overseas Hwy, Marathon, FL
Located in Marathon, The Hammocks at Marathon is by the ocean, within a 10-minute drive of Florida Keys Country Club and Sombrero Beach.
The Hammocks at Marathon
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

Marathon
With a stay at this vacation home in Marathon (Marathon Shores), you'll be within a 10-minute drive of Sombrero Beach and Captain Hooks Marina and Dive ...
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

key colony Beach
With a stay at this vacation home in Key Colony Beach, you'll be on the beach, within a 15-minute drive of Sombrero Beach and Sunset Park Beach.
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Save an average of 15% on thousands of hotels when you're signed in
Next availability from May 18th, 2024  - The Last Resort, Islamorada - MM76.7

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

Islamorada, FL
With a stay at this vacation home in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and 3 minutes by foot from San Pedro Underwater Archaeological ...
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
WOW!   PRIVATE POOL, OCEAN FRONT,  & DOCK Sister house next-door VRBO#1034656

WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

Marathon
With a stay at this vacation home in Marathon (Coral Lagoon), you'll be within a 10-minute drive of Sombrero Beach and Marathon Visitor Center.
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks

Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks

Marathon
With a stay at this vacation home in Marathon (Marathon Shores), you'll be within a 10-minute drive of Sombrero Beach and Captain Hooks Marina and Dive ...
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

Marathon
With a stay at this vacation home in Marathon (Marathon Shores), you'll be within a 10-minute drive of Sombrero Beach and Captain Hooks Marina and Dive ...
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

Marathon
With a stay at this vacation home in Marathon, you'll be on the waterfront, within a 10-minute drive of Sombrero Beach and Marathon Air Museum.
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW
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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.

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

Holiday houses in Duck 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 Duck 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 Duck Key adventures, obvs.

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

Duck Key Holiday Homes essential information

Accommodation
1259 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Hammocks at Marathon, FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays, KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts, Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656, Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water, Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks, Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy., Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

Top trending hotels in Duck Key

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
61 Hawks Cay Blvd, Marathon, FL
Fully refundableReserve now, pay when you stay
Located in Marathon, Hawks Cay Resort is by the ocean, a 4-minute drive from Curry Hammock State Park and 8 minutes from Long Key State Park.
Hawks Cay Resort
Villas At Hawks Cay Resort

Villas At Hawks Cay Resort

4 out of 5
61 Hawks Cay Boulevard, Villas, Marathon, FL
Stay at this 4-star luxury resort in Marathon. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Popular attractions Little Conch Key and Walkers Island ...
Villas At Hawks Cay Resort
Village at Hawks Cay Villas by KeysCaribbean

Village at Hawks Cay Villas by KeysCaribbean

3 out of 5
300 Duck Key Drive, Marathon, FL
Located in Marathon, Village at Hawks Cay Villas by KeysCaribbean is by the ocean, a 3-minute drive from Curry Hammock State Park and 7 minutes from Long Key ...
Village at Hawks Cay Villas by KeysCaribbean
Save an average of 15% on thousands of hotels when you're signed in
Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

5 out of 5
1 Knights Key Boulevard, MM 47, Marathon, FL
Fully refundableReserve now, pay when you stay
With a stay at Isla Bella Beach Resort & Spa in Marathon, you'll be on the beach, just steps from Vaca Key and a 3-minute drive from Seven Mile Bridge.
Isla Bella Beach Resort & Spa
Don't see what you're looking for?
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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.