Book Holiday Homes in Islamorada

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Featured Holiday Homes in Islamorada

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

Key Largo
With a stay at this vacation home in Key Largo, you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina.
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
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
With a stay at this vacation home in Islamorada (Matecumbe), you'll be steps from Sunset Drive Beach and 3 minutes by foot from San Pedro Underwater Archaeological ...
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
With a stay at this vacation home in Key Largo, you'll be within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor Marina.
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Save an average of 15% on thousands of hotels when you're signed in
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Key Largo
With a stay at this vacation home in Key Largo, you'll be on the waterfront, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's ...
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
With a stay at this vacation home in Key Largo, you'll be on the waterfront, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's ...
Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!
NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA

NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA

Key Largo
With a stay at this vacation home, you'll be centrally located in Key Largo, within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock ...
NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA
Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Fun For All! Key Largo 3/3 Townhome Oceanside Resort

Key Largo
With a stay at this vacation home in Key Largo, you'll be on the waterfront, within a 10-minute drive of John Pennekamp Coral Reef State Park and Jimmy Johnson's ...
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
801 Mariners Club Key Largo | 4 Bed, 4 Bath

801 Mariners Club Key Largo | 4 Bed, 4 Bath

Key Largo
With a stay at this vacation home in Key Largo, you'll be by the sea, within a 15-minute drive of John Pennekamp Coral Reef State Park and Bluefin Rock Harbor ...
801 Mariners Club Key Largo | 4 Bed, 4 Bath
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

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

Islamorada
When you stay at this vacation home in Tavernier, you'll be on the beach, within a 5-minute drive of Old Road Gallery and Islamorada County Park.
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
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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
761 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball, Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7, New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities, Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool, Kawama 3 bedroom townhouse--2 heated pools, marina, tennis, lagoon & much more!, NEW OCEANVIEW CASA MAR VOTED #1! INDOOR PICKLEBALL ~ POOLS~ TENNIS~ FISH~ MARINA, Fun For All! Key Largo 3/3 Townhome Oceanside Resort, 801 Mariners Club Key Largo | 4 Bed, 4 Bath, Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Top trending hotels in Islamorada

Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
With a stay at Amara Cay Resort in Islamorada (Matecumbe), you'll be a 4-minute walk from Bud n' Mary's Dive Center and a 2-minute drive from Florida Keys Brewing ...
Amara Cay 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
With a stay at Cheeca Lodge & Spa in Islamorada (Matecumbe), you'll be a 4-minute walk from Matecumbe United Methodist Church and 5 minutes by foot from Florida ...
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
Located in Islamorada (Matecumbe), Chesapeake Beach Resort is within a 5-minute drive of History of Diving Museum and Windley Key Fossil Reef Geological State ...
Chesapeake Beach Resort
Save an average of 15% on thousands of hotels when you're signed in
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
With a stay at Islander Resort in Islamorada (Matecumbe), you'll be steps from Keys History & Discovery Center and 9 minutes by foot from Islamorada Brewery ...
Islander Resort
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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.