Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Villa Largo Island Retreat

Villa Largo Island Retreat

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Villa Largo Island Retreat
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 2-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
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BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS

NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS

Key Largo
With a stay at this vacation home, you'll be centrally located in Key Largo, a 4-minute drive from Jimmy Johnson's Big Chill and 10 minutes from John Pennekamp ...
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral ...
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
Casa Largo

Casa Largo

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the waterfront, a 3-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp ...
Casa Largo
New Caribbean home.  Resort access to pool

New Caribbean home. Resort access to pool

Islamorada
Located in Islamorada (Matecumbe), this vacation home is within a 15-minute walk of Matecumbe United Methodist Church and Florida Keys Brewing Co..
New Caribbean home. Resort access to pool
Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More

Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More
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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.

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

Holiday houses in Islamorada 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 Islamorada 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 Islamorada adventures, obvs.

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

Islamorada Holiday Homes essential information

Accommodation
645 Holiday Homes
Lowest Price
AU$322
Highest Price
AU$490
Popular accommodation
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Villa Largo Island Retreat, Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART, NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS, VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS, Casa Largo, New Caribbean home. Resort access to pool, Marina-View 3BR/3BA Mariner's Club Townhouse 201 with Oasis Pool, Marina, Game Room & More

Top trending hotels in Islamorada

Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
The price is AU$480 per night from 27 Nov to 28 Nov
AU$480
includes taxes & fees
27 Nov - 28 Nov
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$387 per night from 2 Dec to 3 Dec
AU$387
includes taxes & fees
2 Dec - 3 Dec
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and 13 minutes by foot from Indian Key Historic ...
Amara Cay Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$322 per night from 8 Dec to 9 Dec
AU$322
includes taxes & fees
8 Dec - 9 Dec
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Chesapeake Beach Resort
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La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$490 per night from 30 Nov to 1 Dec
AU$490
includes taxes & fees
30 Nov - 1 Dec
With a stay at La Siesta Resort & Villas in Islamorada (Matecumbe), you'll be within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...
La Siesta Resort & Villas
Don't see what you're looking for?
See all available properties in Islamorada
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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.