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Islamorada Cottage Rentals

10.0 (111 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Islamorada Cottage Rentals?

What makes our Cottage Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Islamorada

When should you plan your Cottage Rentals stay?

Choosing the ideal time to visit this destination ensures you enjoy pleasant weather and optimal conditions for relaxing in your preferred cottages, making your stay here truly memorable.

Peak Season Highlights

spring
March to May

During spring, you'll experience warm days ideal for enjoying the region's pristine beaches and outdoor activities. This is when the area sees an influx of visitors seeking pleasant weather and vibrant marine life.

Average Temperature Daytime: 78°F to 85°F - Nighttime: 65°F to 72°F
spring
December to February

Winter months attract travelers looking to escape colder climates, with mild temperatures that make exploring the area comfortable and enjoyable year-round. Expect this period to be lively with holiday festivities and scenic views.

Average Temperature Daytime: 70°F to 75°F - Nighttime: 60°F to 65°F

Off-Season Highlights

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June to August

Summer offers quieter times for those seeking a more relaxed experience, although it can be quite hot and humid. It's a great period to find peaceful cottages away from the crowds while still enjoying warm water activities.

Average Temperature Daytime: 88°F to 92°F - Nighttime: 75°F to 79°F
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September to November

Fall provides a shoulder season with fewer visitors, making it perfect for peaceful stays and exploring at leisure. The weather remains warm, and the region's natural beauty is especially captivating during this time.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 68°F to 73°F

Weekly Weather Forecast for Islamorada

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy private outdoor dining areas perfect for savoring meals while taking in the coastal views.
  • Take advantage of lush landscaped gardens and shaded patios that create a tranquil outdoor environment.
  • Relax by your own swimming pool or hot tub, ideal for unwinding after a day of exploring the region.
  • Make use of outdoor grills and BBQ facilities to host cookouts with family and friends.
  • Benefit from direct access to scenic waterfronts or beaches, perfect for water-based activities.
  • Utilize boat docks or marinas nearby for easy day trips on the water.
  • Experience outdoor recreational spaces such as walking paths or nature trails within the property grounds.
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Family Activities

  • Fishing Charters: Experience a family-friendly fishing adventure, where you can learn to cast and reel in local species along the scenic waters.
  • John Pennekamp Coral Reef State Park: Discover vibrant coral reefs and marine life through guided snorkeling tours perfect for all ages in this tropical destination.
  • Wildlife Watching at Blue Heron Bridge: Enjoy observing native birds, marine creatures, and other wildlife in their natural habitat, suitable for curious young explorers.
  • Rain Barrel Art & Nature Preserve: Engage with nature through interactive exhibits and outdoor activities that celebrate the area's lush environment and local art.
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Adult Activities

  • Fishing Charters: Experience the thrill of deep-sea fishing with guided charters that take you into the vibrant waters surrounding this destination, perfect for anglers seeking adventure.
  • Water Sports: Engage in exhilarating water activities such as paddleboarding, kayaking, or jet skiing to explore the beautiful coastline at your own pace.
  • Dining Experiences: Savor fresh seafood and local cuisine at renowned restaurants offering stunning views, making every meal memorable during your stay.
  • Sunset Cruises: Relax aboard a sunset cruise to enjoy breathtaking views and unwind as the sun dips below the horizon, a must-do activity in this region.

Other Places to Stay in Islamorada, FL

History of Diving Museum
Windley Key Fossil Reef Geological State Park
Seabreeze Trailer Park
Upper Matecumbe Key
Theater of the Sea
Matecumbe United Methodist Church
Plantation by the Sea
White Marlin Beach
Toll Gate Shores
Venetian Shores
Lower Matecumbe Beach

Islamorada Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Ahead: Take advantage of the area's renowned fishing, snorkeling, and boating opportunities by scheduling them in advance to ensure a memorable experience.
  • Choose a Strategic Location: Opt for cottages situated near the water or popular spots to maximize relaxation and easy access to local attractions.
  • Explore Local Dining and Shops: Immerse yourself in the region's vibrant culture by visiting nearby eateries and boutiques that showcase the area's unique charm.
  • Prepare for Florida Weather: Pack versatile clothing and sun protection gear to enjoy the outdoor activities regardless of the weather conditions here.

Transportation Options

  • Car Rentals: Renting a car in this region offers the flexibility to explore the scenic coastline and nearby attractions at your own pace, making it an ideal choice when staying in cottages here.
  • Taxi Services: Taxis provide convenient transportation around the area for quick trips or when you prefer not to drive yourself during your stay.
  • Rental Bicycles: Exploring the area via bicycle allows you to enjoy the natural beauty and tranquil surroundings while easily accessing local amenities close to your cottages.
  • Public Transit: Local buses connect key spots within the region, offering an economical way to get around while relaxing and taking in the scenery from your accommodations.

Local Customs Options

  • Respect for Mosques and Religious Sites: When visiting local mosques, it is customary to dress modestly and remove your shoes as a sign of respect for Islamic traditions here.
  • Greetings: Offering a traditional greeting such as "As-Salamu Alaykum" is appreciated when interacting with the Muslim community in this destination.
  • Dietary Laws: Be mindful of halal dietary practices, especially when dining out or purchasing food, to honor local customs rooted in Islamic faith here.
  • Community Observances: Participating or observing during Islamic holidays and prayer times demonstrates cultural sensitivity within the region's Muslim community.

Frequently Asked Questions About Islamorada Rental Cottages

1. How many Cottages are available in Islamorada?

Currently, the total number of properties listed by RBO in 2026 is over 13 in the Islamorada area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Cottages in Islamorada. 

2. What is the cancellation policy for cottages in this area?

Cancellation policies vary by property. You should review the specific cottage listing for details on deadlines, fees, and refunds. If you have questions, contacting the property owner directly can provide clarity.

3. Are pets allowed in the cottages near here?

Pet policies differ among properties. Check each listing to confirm if pets are permitted, and any additional fees or restrictions that may apply.

4. What amenities are typically included with cottages in this destination?

Amenities vary but often include essentials such as Wi-Fi, kitchen facilities, and outdoor space. Detailed information about what’s provided is available on each listing, so reviewing the property’s features is recommended.

5. How do I know if a cottage is available for my travel dates?

Availability depends on the specific property. Use the booking platform’s calendar to check real-time availability or contact the property owner for confirmation.

6. What should I do if I need assistance during my stay?

Most properties offer contact information for local hosts or property managers. Reaching out to them directly will ensure you get prompt support during your visit.