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, laundry facilities, and patios. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp Coral ...
Opens in a new windowWaterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Sea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat

Sea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat

Key Largo
The price is NZ$1,536 per night from 20 Sept to 21 Sept
NZ$1,536
20 Sept - 21 Sept
includes taxes & fees
Book a stay at this family-friendly vacation home in Key Largo. Enjoy free WiFi, a water park, and a fitness center. Our guests praise the helpful staff in our ...
Opens in a new windowSea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat
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 ...
Opens in a new windowNext availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7
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OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

Islamorada
Book a stay at this beach vacation home in Islamorada. Enjoy free WiFi, a beach locale, and laundry facilities. Our guests praise the pool and the helpful staff ...
Opens in a new windowOCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo
Book a stay at this family-friendly vacation home in Key Largo. Enjoy a fitness center, laundry facilities, and concierge services. Popular attractions Jimmy ...
Opens in a new windowMariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

Key Largo
Book a stay at this family-friendly vacation home in Key Largo. Enjoy a fitness center, laundry facilities, and tennis courts. Popular attractions Jimmy Johnson's ...
Opens in a new windowResort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Kawama L4 - Upscale Oceanside Villa with Marina

Kawama L4 - Upscale Oceanside Villa with Marina

Key Largo
Stay at this vacation home in Key Largo. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowKawama L4 - Upscale Oceanside Villa with Marina
Beautiful Oceanside Mariner's 3 Bedroom Townhome

Beautiful Oceanside Mariner's 3 Bedroom Townhome

Key Largo
Stay at this vacation home in Key Largo. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Jimmy Johnson's Big Chill and John Pennekamp ...
Opens in a new windowBeautiful Oceanside Mariner's 3 Bedroom Townhome
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 ...
Opens in a new windowBRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
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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
732 Holiday Homes
Lowest Price
NZ$288
Highest Price
NZ$1,536
Popular accommodation
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Sea La Vie! Fall Deals & Spring Openings- 4BR Key Largo Retreat , Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!, Kawama L4 - Upscale Oceanside Villa with Marina, Beautiful Oceanside Mariner's 3 Bedroom Townhome, BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART

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$288 per night from 30 Sept to 1 Oct
NZ$288
30 Sept - 1 Oct
includes taxes & fees
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 ...
Opens in a new windowCheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$315 per night from 24 Sept to 25 Sept
NZ$315
24 Sept - 25 Sept
includes taxes & fees
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ...
Opens in a new windowChesapeake Beach Resort
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$420 per night from 21 Sept to 22 Sept
NZ$420
21 Sept - 22 Sept
includes taxes & fees
Stay at this 4-star beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the bar in our reviews. ...
Opens in a new windowAmara Cay Resort
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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 NZ$416 per night from 1 Oct to 2 Oct
NZ$416
1 Oct - 2 Oct
includes taxes & fees
Stay at this 3.5-star beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowThree Waters Resort and Marina, Islamorada, a Tribute Portfolio 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.