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
Stay at this vacation home in Key Largo. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Jimmy Johnson's Big Chill and 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
Stay at this vacation home in Key Largo. Enjoy free WiFi, a garden, and patios. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral Reef State ...
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
Stay at this vacation home in Key Largo. Enjoy free WiFi, cable/satellite TV service, and an in-room coffeemaker. Our guests praise the helpful staff in our ...
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
Book a stay at this beach vacation home in Key Largo. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Jimmy Johnson's Big Chill and John ...
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
Book a stay at this beach vacation home in Islamorada. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Robbie’s of Islamorada and Indian ...
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
Stay at this vacation home in Key Largo. Enjoy tennis courts, patios, and cable/satellite TV service. Popular attractions Jimmy Johnson's Big Chill and John ...
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
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and patios. Popular attractions 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
Book a stay at this family-friendly vacation home in Key Largo. Enjoy free WiFi, tennis courts, and patios. Popular attractions Jimmy Johnson's Big Chill and ...
VOTED TRIPADVISOR'S #1 DESTINATION 5 REMODELED UNITS! KAYAKS, MARINA, TENNIS
BEACHFRONT POOL HOME

BEACHFRONT POOL HOME

Key Largo
Book a stay at this beach vacation home in Key Largo. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Jimmy Johnson's Big Chill and Bluefin ...
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
772 Holiday Homes
Lowest Price
NZ$598
Highest Price
NZ$1,599
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 NZ$609 per night from 6 Apr to 7 Apr
NZ$609
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
Chesapeake Beach 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 NZ$1,599 per night from 1 May to 2 May
NZ$1,599
includes taxes & fees
1 May - 2 May
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
The price is NZ$780 per night from 27 Apr to 28 Apr
NZ$780
includes taxes & fees
27 Apr - 28 Apr
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
Amara Cay Resort
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Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$598 per night from 27 Apr to 28 Apr
NZ$598
includes taxes & fees
27 Apr - 28 Apr
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Islander Resort
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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.