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 John Pennekamp Coral Reef State Park and ...
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Villa Largo Island Retreat

Villa Largo Island Retreat

Key Largo
Stay at this vacation home in Key Largo. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Jimmy Johnson's Big Chill ...
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
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!
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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
Book a stay at this beach vacation home in Key Largo. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
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
Book a stay at this beach vacation home in Key Largo. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the helpful staff in our reviews. ...
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
Book a stay at this beach vacation home in Key Largo. Enjoy free WiFi, a beach locale, and a water park. Popular attractions John Pennekamp Coral Reef State ...
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION, KAYAKS, MARINA, POOL TENNIS
Casa Largo

Casa Largo

Key Largo
Stay at this vacation home in Key Largo. Enjoy a marina, tennis courts, and patios. Popular attractions John Pennekamp Coral Reef State Park and Jacob's Aquatic ...
Casa Largo
New Caribbean home.  Resort access to pool

New Caribbean home. Resort access to pool

Islamorada
Stay at this vacation home in Islamorada. Enjoy a beach locale, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Keys History & Discovery ...
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
Stay at this vacation home in Key Largo. Enjoy a fitness center, cable/satellite TV service, and in-room jetted tubs. Popular attractions John Pennekamp Coral ...
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
NZ$359
Highest Price
NZ$1,075
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
Fully refundableReserve now, pay when you stay
The price is NZ$1,075 per night from 8 Dec to 9 Dec
NZ$1,075
includes taxes & fees
8 Dec - 9 Dec
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
Fully refundableReserve now, pay when you stay
The price is NZ$427 per night from 2 Dec to 3 Dec
NZ$427
includes taxes & fees
2 Dec - 3 Dec
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
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$359 per night from 8 Dec to 9 Dec
NZ$359
includes taxes & fees
8 Dec - 9 Dec
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
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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 NZ$546 per night from 30 Nov to 1 Dec
NZ$546
includes taxes & fees
30 Nov - 1 Dec
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
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.