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
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!
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Key Largo
With a stay at this vacation home in Key Largo, you'll be a 4-minute drive from Jimmy Johnson's Big Chill and 9 minutes from John Pennekamp Coral Reef State ...
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)
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Beautiful Updated Kawama Townhouse.  Marina, boat ramp, lagoon and pools.

Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.

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 ...
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
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
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 out of 5
Key Largo
Located in Key Largo, this vacation home is within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State Park.
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
5 bedroom - Deep Dockage & Heated Pool in Islamorada.

5 bedroom - Deep Dockage & Heated Pool in Islamorada.

Islamorada
A stay at this vacation home places you in the heart of Islamorada, within a 10-minute walk of Keys History & Discovery Center and Islamorada Brewery & ...
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS!  KAYAKS, MARINA, TENNIS

VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS

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 ...
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS
BEACHFRONT POOL HOME

BEACHFRONT POOL HOME

Key Largo
When you stay at this vacation home in Key Largo, you'll be on the beach, within a 15-minute drive of Jimmy Johnson's Big Chill and John Pennekamp Coral Reef ...
BEACHFRONT POOL HOME
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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
748 Holiday Homes
Lowest Price
AU$535
Highest Price
AU$616
Popular accommodation
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside), Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools., Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities, 5 bedroom - Deep Dockage & Heated Pool in Islamorada., VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS, BEACHFRONT POOL HOME

Top trending hotels in Islamorada

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$535 per night from 28 Apr to 29 Apr
AU$535
includes taxes & fees
28 Apr - 29 Apr
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
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$597 per night from 12 May to 13 May
AU$597
includes taxes & fees
12 May - 13 May
Located in Islamorada, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort is by the ocean, within a 5-minute drive of Windley Key Fossil ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is AU$616 per night from 4 May to 5 May
AU$616
includes taxes & fees
4 May - 5 May
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
Save an average of 15% on thousands of hotels when you're signed in
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$542 per night from 27 Apr to 28 Apr
AU$542
includes taxes & fees
27 Apr - 28 Apr
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
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.

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^Subject to availability and chosen travel dates.