Vacation rentals in Islamorada, United States

Carefully selected & verified rentals in Islamorada, United States
Check-in
20Oct2025Select date
Check-out
21Oct2025Select date
Rooms and Guests2 Guests, 1 Room
Islamorada offers attractions like Anne's Beach, where you can sunbathe, and the Florida Keys History & Discovery Center, where you can learn about the area's rich past. For water activities, visit the Islander Watersports for kayaking and paddleboarding. You'll find beachfront hotels like the Moorings Village and Postcard Inn that feature ocean views and direct access to sandy shores. With a carefully selected range of accommodations, you're sure to find the ideal spot for your stay. Book early, especially in peak season, to secure the best deals and plan your experience around local events.
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1-11 out of 11
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  • Price: high to low
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Ocean View Duplex Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key One Islamorada
Map12.8 km from City Centre
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Ocean View Two Duplex Penthouses Retreat Amenities: Tennis Court Heated Pool Vista Key Islamorada
Map12.7 km from City Centre
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Ocean View Penthouse Retreat Amenities: Tennis Court Heated Pool Vista Key Two
Map12.8 km from City Centre700 m from
FromUS$ 1 446 /nightSelect
Islamorada Retreat For 2
Map6.8 km from City Centre
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Beacon Reef #204
Map1.3 km from City Centre300 m from History of Diving Museum
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Beacon Reef Condo Oceanside
Map1.3 km from City Centre300 m from History of Diving Museum
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Escape To The Keys
MapProximity to Theater Of The Sea4.9km
  • Outdoor swimming pool access
  • Private beach area available
  • Fully equipped kitchen in rooms
  • Outdoor pool
  • Private beach
  • Heated pool
Resort featuring private beach and outdoor activities.
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Little Bay Upper
MapUpper Matecumbe Key1.1km
  • Balconies with beautiful views
  • On-site water park available
  • Fitness centre and spa amenities
  • Water park
  • Fitness centre
  • Spa
Hotel offering water sports and wellness facilities
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Little Bay Lower
MapUpper Matecumbe Key1.1km
  • On-site spa and wellness centre available
  • Water park with various activities offered
  • Diving and snorkelling opportunities nearby
  • Water park
  • Spa Centre
  • Diving Activities
Resort featuring a water park and wellness amenities
FromUS$ 621 /nightSelect
Little Bay Prime
MapUpper Matecumbe Key1.1km
  • Beachfront property with water park
  • On-site fitness center and spa amenities
  • Diverse water sports and activities available
  • Water park
  • Fitness center
  • Spa services
Beachfront hotel offering water sports and wellness services
FromUS$ 1 510 /nightSelect
Executive Bay Club Condo M-1
The largest option:
6 adults
2 bedrooms
3 beds
MapBeautiful natural setting3.7km
  • Private beach access and outdoor pool
  • Fully equipped kitchenette in all rooms
  • On-site activities like cycling and fishing
  • Outdoor pool
  • Private beach
  • Fully equipped kitchenette
Resort with beachfront access and recreational activities
FromUS$ 150 /nightSelect

Flexible Price Range for Vacation Homes in Islamorada

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 1 510
⬇️ The lowest price
US$ 150
đź’¸ Average price for
Apartments
US$ 930

FAQs about Islamorada rentals

Get answers to common questions and plan your adventure smoothly

What are the top-rated vacation rentals in Islamorada according to guest reviews?
Angler'S Reef Resort and Little Bay Upper consistently receive high ratings for their accommodations and views, making them popular choices.
Which vacation rentals in Islamorada are close to popular landmarks?
Executive Bay Club Condos is conveniently located near the Anne's Beach Park, just 1.6 km away, making it easy to explore local attractions.
Are there vacation rentals in Islamorada with unique views?
Little Bay Lower and Beacon Reef #204 offer stunning ocean views that enhance your stay with scenic beauty and relaxing atmospheres.
What is the cheapest vacation rental option in Islamorada?
Little Bay Prime often offers the most budget-friendly rates, typically around $150 USD per night during the off-peak season.
Check-in
20Oct2025Select date
Check-out
21Oct2025Select date
Rooms and Guests2 Guests, 1 Room