
Islamorada Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Islamorada vacation rentals


Island Sanctuary Islamorada
Island Sanctuary Islamorada
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Florida Keys Getaway - Slps 4 - Ocean View
Florida Keys Getaway - Slps 4 - Ocean View
Charming Home in Key Largo
Charming Home in Key LargoFind vacation rentals that suit your style
Top Islamorada Hotel Reviews

Hadley Resort and Marina
Find out more about Islamorada
Everything you need to know about Islamorada vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Islamorada vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Islamorada vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Islamorada vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Islamorada. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Islamorada vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Islamorada vacation rentals we have selected for you start as low as CA $213 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Islamorada rentals
At Expedia, we put the best Islamorada vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Islamorada rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Islamorada vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Islamorada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Cottages in Islamorada
- Port Antigua Retreat on Canal with Boat Lift and Private Beach Access
- Pirates Cove Hotels
- Layton Hotels
- Hotels near Jimmy Johnson's Big Chill
- Family Hotels in Islamorada
- Tavernier Hotels
- Hotels with Waterslides in Islamorada
- Family Hotels in Key Largo
- Rv Parks in Lower Matecumbe Key
- Romantic Hotels in Key Largo
- Vacation Homes in Layton
- Beach Hotel Hotels in Islamorada
- Breathtaking Ocean views! Owners who care. “Sangria Sunrise”! 10% off charters!
- Tropical Escape
- B&B in Tavernier
- All Inclusive Resorts and in Key Largo
- Resorts in Upper Matecumbe Key
- Oceanfront Hotels in Pirates Cove
- Rv Parks in Lignumvitae Key Botanical State Park
- Beach Hotel Hotels in Long Key
- Condo Rentals in Key Largo
- Long Key Hotels
- Amoray Dive Resort
- Hotels with smoking rooms in Islamorada
- Wyndham Hotels in Islamorada
- All Inclusive Resorts and in Islamorada
- Manatee Manor ~ 3 Bedroom Island Home on Plantation Key with Pool & Dockage
- Best Western Hotels in Key Largo
- Hotels near Baker's Cay Resort Beach
- Motels in Islamorada
- Matecumbe Hotels
- Waterfront Home With Swimming Pool
- Bayside Villas by Islander Resort
- Hotels near Everglades National Park
- Apartments in Layton
- Islamorada Hotels
- La Siesta Resort & Villas
- Beach Hotel Hotels in Key Largo
- Direct Oceanfront Corner Condo
- Oceanfront Hotels in Islamorada
- Pineapple Beach by Florida Keys Luxury Rentals
- Cottages in Key Largo
- Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex
- Hotels with Free Airport Shuttle in Islamorada
- Resorts in Key Largo
- Hotels with Kitchenettes in Key Largo
- Inns in Islamorada
- Hersha Hospitality Hotels in Upper Matecumbe Key
- Luxury Hotels in Key Largo
- Motels in Key Largo
- Luxury Hotels in Islamorada
- Cheap Hotels in Key Largo
- Houseboats in Windley Key
- Cheap Hotels in Islamorada
- Wynken Blynken and Nod Hotels
- Houseboats in Key Largo
- Oceanfront Hotels in Key Largo
- Boutique Hotels in Islamorada
- Barefoot Bliss
- Stunning Direct Ocean Views from 2BR Suite
- Adults Only Resorts & in Key Largo
- Keys Waterfront Condo
- Key Largo Hotels
- Fish
- History of Diving Museum
- Baker's Cay Resort Beach
- Visit Lower Matecumbe Key
- Islamorada Vacations
- Visit Islamorada
- Visit Seabreeze Trailer Park
- Key Largo Vacations
- Visit Long Key
- Visit Key Largo
- Anne's Beach
- Visit Upper Matecumbe Key
- Sombrero Beach
- All inclusive Vacation Packages Key Largo
- Visit Layton
- Visit Plantation Key



















































































