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

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
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

Islamorada
Book a stay at this beach vacation home in Islamorada. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Windley Key Fossil Reef Geological ...
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
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 ...
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Save an average of 15% on thousands of hotels when you're signed in
Florida Keys Townhouse For Rent 2/2

Florida Keys Townhouse For Rent 2/2

Key Largo
Book a stay at this family-friendly vacation home in Key Largo. Enjoy laundry facilities, tennis courts, and patios. Popular attractions Jimmy Johnson's Big ...
Florida Keys Townhouse For Rent 2/2
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 ...
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Charming Home in Key Largo

Charming Home in Key Largo

Key Largo
The price is NZ$575 per night from 6 Aug to 7 Aug
NZ$575
6 Aug - 7 Aug
includes taxes & fees
Stay at this vacation home in Key Largo. Enjoy a garden, laundry facilities, and an in-room coffeemaker. Popular attractions Jimmy Johnson's Big Chill and Harry ...
Charming Home in Key Largo
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

Islamorada
Book a stay at this family-friendly vacation home in Islamorada. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Windley Key Fossil ...
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

Islamorada
Stay at this vacation home in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Keys History & Discovery Center and Islamorada ...
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

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 Jimmy Johnson's Big Chill and ...
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
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
761 Holiday Homes
Lowest Price
NZ$348
Highest Price
NZ$575
Popular accommodation
Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards, Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Florida Keys Townhouse For Rent 2/2, OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars, Charming Home in Key Largo, NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony, 7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks , Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

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$447 per night from 14 Aug to 15 Aug
NZ$447
14 Aug - 15 Aug
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 ...
Cheeca 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$348 per night from 10 Aug to 11 Aug
NZ$348
10 Aug - 11 Aug
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. ...
Chesapeake Beach Resort
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is NZ$510 per night from 11 Aug to 12 Aug
NZ$510
11 Aug - 12 Aug
includes taxes & fees
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
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 NZ$415 per night from 1 Sept to 2 Sept
NZ$415
1 Sept - 2 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. ...
Amara Cay Resort
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.