Holiday Rentals in Islamorada
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.
Check rental availability in Islamorada
Holiday Rentals in Islamorada

Breezy Palms Resort

The Islands of Islamorada

Treasure Harbor

Next availability from May 18th, 2024 - The Last Resort, Islamorada - MM76.7

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

Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

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

Islamorada Boaters Paradise with 70' Dock and private beach access..

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

Tranquility Cove Beautiful Remodeled home in the heart of Islamorada.

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

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

Ocean View Duplex Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key One

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada
Other types of properties in Islamorada you may be interested in

Cheeca Lodge & Spa
Holiday Accommodation Islamorada
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Islamorada are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Islamorada itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Islamorada holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Islamorada, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Islamorada with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Top Holiday Rental Destinations
More accommodation in Islamorada
Top 20 Islamorada Hotels
More destinations for you
- Hotels with a Waterpark in Pensacola
- Melbourne Accommodation
- Hotels with a Waterpark in Destin
- Beach Hotels in Tallahassee
- Davenport Accommodation
- Romantic Hotels in Tallahassee
- Hotels with a Waterpark in St. Augustine
- Hotels with a Waterpark in Daytona Beach
- Christmas Accommodation
- All Inclusive Hotels in Daytona Beach
- St. Augustine Accommodation
- All Inclusive Hotels in Pensacola Beach
- Pet Friendly Hotels in Palm Beach
- Pet Friendly Hotels in Clermont
- Daytona Beach Accommodation
- Luxury Hotels in Cape Canaveral
- North Port Accommodation
- Key West Accommodation
- Luxury Hotels in Titusville
- Panama City Beach Accommodation