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Islamorada Rentals by Owner

Why Choose Rent By Owner for your Islamorada vacation rental?

What makes our Rentals by Owner 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 Rentals by Owner stay?

Choosing the ideal time to vacation in this destination can enhance your experience, as the region offers various seasonal attractions and weather conditions perfect for different preferences when booking a rental by owner through Rent By Owner.

Peak Season Highlights

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Winter (December to February)

During the winter months, this destination experiences its peak season as visitors escape colder climates to enjoy warm weather and sunny skies in the area.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
spring
Spring Break (March to April)

Spring break attracts many travelers to the region, making it one of the busiest times for booking vacation rentals by owner due to favorable weather and vibrant local activities.

Average Temperature Daytime: 78°F to 82°F - Nighttime: 68°F to 72°F

Off-Season Highlights

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Summer (June to August)

The summer months see a dip in visitor numbers compared to the winter peak, but you can still enjoy warm waters and fewer crowds while exploring the area’s natural beauty.

Average Temperature Daytime: 88°F to 92°F - Nighttime: 77°F to 80°F
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Fall (September to November)

Fall offers a quieter experience with pleasant weather and fewer tourists, making it an ideal time to book rental accommodations by owner without the peak season prices.

Average Temperature Daytime: 80°F to 85°F - Nighttime: 70°F to 75°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

  • Access to private or community boat docks for exploring the surrounding waters
  • Outdoor grilling areas or barbecue stations for enjoying meals alfresco
  • Patio or deck spaces with comfortable outdoor furniture to relax and unwind
  • Swimming pools, including infinity pools or heated options, for cooling off in the sun
  • Shaded outdoor pavilions or gazebos ideal for gatherings or shaded lounging
  • Direct beach access or shoreline views to take in the scenic coastal scenery
  • Outdoor showers to rinse off after water activities or beach visits
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Family Activities

  • Visit the History of Diving Museum: Explore the fascinating exhibits that highlight the region's diving heritage, offering an educational experience for the whole family.
  • Enjoy a Day at Founders Park: Relax on the scenic beaches, let the kids play in the playgrounds, or take advantage of the picnic areas in this popular local park.
  • Discover Theater of the Sea Marine Park: Experience interactive marine shows and meet dolphins, sea lions, and other aquatic creatures in this engaging attraction nearby.
  • Try Water Sports Adventures: Rent kayaks, paddleboards, or take a family-friendly snorkeling tour to explore the vibrant waters of the area together.
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Adult Activities

  • Deep-Sea Fishing: Experience the thrill of deep-sea fishing excursions, renowned in the area for their abundant marine life and expert-guided trips.
  • Snorkeling and Diving: Explore vibrant coral reefs and diverse marine ecosystems that make this destination a premier spot for underwater adventures.
  • Paddleboarding and Kayaking: Enjoy tranquil waters by paddling along scenic coastlines or through mangrove tunnels, offering both relaxation and adventure.
  • Sunset Cruises: Embark on scenic boat rides to witness breathtaking sunsets over the water, creating memorable moments in this coastal 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 Early: To make the most of your time here, research and reserve popular water activities and tours in advance through your rental by owner to ensure availability.
  • Select a waterfront property: Opt for a vacation rental with direct access to the water to enjoy the scenic views and easy participation in boating, fishing, or kayaking.
  • Explore local dining options: Take advantage of nearby eateries and hidden gems within the area to savor authentic flavors unique to this destination's coastal culture.
  • Respect the environment: Practice eco-friendly habits during your stay to preserve this region’s natural beauty and ensure enjoyment for future visitors.

Transportation Options

  • Rental Cars: You can easily rent a car here for flexible exploration of the area’s scenic waterways and nearby attractions.
  • Taxis and Rideshare Services: Taxis and popular rideshare options provide convenient transportation to enjoy the region without the hassle of parking.
  • Bicycle Rentals: Biking is a great way to experience the tranquil surroundings and access the region’s picturesque coastal paths.
  • Public Transportation: Limited but available local transit options can help you navigate around the area efficiently during your stay.

Local Customs Options

  • Respect for Local Religious Practices: You’ll find that observing Islamic customs, such as modest dress and considerate behavior during prayers, is appreciated in community spaces here, reflecting the area's diverse cultural fabric.
  • Greeting Etiquette: When meeting locals, a warm and respectful greeting is customary, often accompanied by a handshake or verbal salutation, embodying the region's welcoming spirit.
  • Respect for Prayer Times: During prayer periods, you might notice quiet reflection or pauses, making it thoughtful to plan your activities around these times when visiting local attractions or enjoying your rental stay.
  • Dietary Considerations: Many establishments and markets cater to Halal dietary needs, so respecting these preferences ensures an authentic experience in this vibrant destination.

Islamorada Rentals by Owner Frequently Asked Questions

2. How many Vacation Rentals are available in Islamorada?

Currently, the total number of properties listed by RBO in 2026 is over 1209 in the Islamorada area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Islamorada. 

3. What is the cancellation policy for a rental by owner in Islamorada, Florida?

The cancellation policy varies depending on the specific listing. You should review the rental’s details or contact the owner directly to understand the terms and any applicable fees.

4. How do I ensure the rental property in Florida meets my needs before booking?

You can review the detailed description, amenities, and photos provided in the listing. If you have specific questions, reaching out to the owner can help clarify whether the property suits your plans.

5. What safety measures are typically included in rentals in the area?

Safety features such as secure locks, fire alarms, and first aid kits are generally listed in the property details. Confirming these with the owner ensures the rental meets your safety expectations.

6. Can I modify or extend my stay at a rental in Islamorada, Florida?

Any changes to your reservation, including extensions, should be discussed directly with the owner through the booking platform to confirm availability and terms.

7. Are pets allowed in rentals by owner in this destination?

Pet policies differ by listing. You should check the property's rules or contact the owner beforehand to ensure your pets are welcome during your stay.

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