Book Holiday Homes in Islamorada

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Islamorada

VOTED BEST KEY LARGO VACATION RENTAL

VOTED BEST KEY LARGO VACATION RENTAL

Key Largo
Book a stay at this family-friendly vacation home in Key Largo. Enjoy free WiFi, a water park, and a garden. Popular attractions John Pennekamp Coral Reef State ...
VOTED BEST KEY LARGO VACATION RENTAL
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
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property

Islamorada
Book a stay at this beach vacation home in Islamorada. Enjoy a beach locale, concierge services, and balconies. Popular attractions Bud n' Mary's Dive Center ...
Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property
Save an average of 15% on thousands of hotels when you're signed in
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Tavernier
Book a stay at this beach vacation home in Tavernier. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Old Road Gallery and Founders Park ...
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
811 Mariners Club Key Largo | 4 Bed, 3 Bath

811 Mariners Club Key Largo | 4 Bed, 3 Bath

Key Largo
Stay at this vacation home in Key Largo. Enjoy free WiFi, a fitness center, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
811 Mariners Club Key Largo | 4 Bed, 3 Bath
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 family-friendly vacation home in Key Largo. Enjoy free WiFi, a water park, and tennis courts. Popular attractions John Pennekamp Coral Reef ...
Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools.
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath

701 Mariners Club Key Largo | 3 Bed, 3.5 Bath

Key Largo
Stay at this vacation home in Key Largo. Enjoy free WiFi, a fitness center, and tennis courts. Popular attractions John Pennekamp Coral Reef State Park and Bluefin ...
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath
Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Charming Canal-Front House | WiFi+Swim+Kayak+Fish

Tavernier
Stay at this vacation home in Tavernier. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Harry Harris Park and Florida Keys Dive ...
Charming Canal-Front House | WiFi+Swim+Kayak+Fish
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)
Don't see what you're looking for?
See all available properties in Islamorada
View all properties
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
684 Holiday Homes
Lowest Price
NZ$408
Highest Price
NZ$648
Popular accommodation
VOTED BEST KEY LARGO VACATION RENTAL, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Comfort and Relaxation! Balcony, Free Parking, Pool, Pet-friendly Property, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly, 811 Mariners Club Key Largo | 4 Bed, 3 Bath, Beautiful Updated Kawama Townhouse. Marina, boat ramp, lagoon and pools., 701 Mariners Club Key Largo | 3 Bed, 3.5 Bath, Charming Canal-Front House | WiFi+Swim+Kayak+Fish, Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

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$648 per night from 12 Jan to 13 Jan
NZ$648
includes taxes & fees
12 Jan - 13 Jan
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$625 per night from 9 Jan to 10 Jan
NZ$625
includes taxes & fees
9 Jan - 10 Jan
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$408 per night from 8 Jan to 9 Jan
NZ$408
includes taxes & fees
8 Jan - 9 Jan
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
Save an average of 15% on thousands of hotels when you're signed in
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$598 per night from 14 Jan to 15 Jan
NZ$598
includes taxes & fees
14 Jan - 15 Jan
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
View all properties
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.