Owner Direct Vacation
Rentals in Islamorada
The Best Owner Direct Vacation Rentals in Islamorada. Explore thousands of vacation home rentals, large cabins, and villas near Islamorada
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Explore the Best Islamorada Vacation Homes
Looking for the perfect place to stay in Islamorada? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Islamorada character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Find Islamorada Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
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Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Islamorada
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Popular Neighborhoods for Islamorada Vacation Rentals
What are the best areas to stay in Islamorada
Discover the top neighborhoods in Islamorada and choose a place that suits your stay.
Wednesday Jan 28
Islamorada, Florida
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Islamorada vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Islamorada
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How to Reserve Your Islamorada Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Islamorada Vacation Rental FAQs
1. What are the top vacation rentals in Islamorada?
There are a lot of options in Islamorada. If you plan on staying in the Islamorada area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Islamorada:
- OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
- ISLAMORADA, ANGLERS REEF PRISTINE HOME Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- Oceanside Getaway: Renovated Home with Boat Slip, Pool & Beach - Gated community
- The Caribbean Resort
- AQUAMARINE OCEANVIEW+”SPECIAL RATES”+nDOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
2. How many vacation rentals have private pools in Islamorada?
There are 259 vacation rentals with private pools near Islamorada. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Islamorada are best for families?
If you are looking for a family-friendly vacation home in Islamorada, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Islamorada:
4. How many vacation rentals are available in Islamorada?
Currently, the total number of properties listed in 2026 is over 1519 in the Islamorada area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Islamorada.