Discover Your Perfect Toll Gate Shores Vacation Homes

Best Vacation Homes in Toll Gate Shores

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8.8 (61 Reviews)
Condo
Topsider Resort
  • Air Conditioner
  • Parking
  • Pool
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Toll Gate Shores Luxury Rentals

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Toll Gate Shores Pet Friendly Vacation Rentals

10.0 (8 Reviews)
House
Beautiful Beach Home
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
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Why Choose Rent By Owner for your Toll Gate Shores Vacation Rental Homes?

What makes our Vacation 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 Toll Gate Shores

When should you plan your Vacation Rentals stay?

Choosing the optimal time to vacation here can enhance your experience, as the region offers ideal weather and vibrant local activities during specific seasons, making it essential to plan accordingly for a memorable stay in Toll Gate Shores, Islamorada, Florida.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, this destination experiences its peak season with warm weather and ideal conditions for outdoor activities. You’ll enjoy pleasant daytime temperatures perfect for exploring and relaxing in the region's scenic surroundings.

Average Temperature Daytime: 78°F - Nighttime: 65°F
spring
Spring (March to May)

Spring marks another high point when visitors flock here for mild temperatures and vibrant natural beauty. It’s an excellent time to book vacation rentals and immerse yourself in the area's welcoming climate.

Average Temperature Daytime: 82°F - Nighttime: 70°F

Off-Season Highlights

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Summer (June to August)

The summer months see a slowdown in tourist traffic, making it a good time to find more affordable vacation rentals with less crowding. Expect hot weather and increased humidity in this region during this period.

Average Temperature Daytime: 88°F - Nighttime: 75°F
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Fall (September to November)

Autumn can be quieter here as many travelers avoid the early part of hurricane season. This is a suitable period for those seeking more tranquility and better deals on vacation rentals.

Average Temperature Daytime: 83°F - Nighttime: 72°F

Weekly Weather Forecast for Toll Gate Shores

How to Book Your Toll Gate Shores Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

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.

Explore and book the perfect rental in Toll Gate Shores

More Top-Rated Vacation Rentals in Toll Gate Shores Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 shared outdoor swimming pools to enjoy the warm Florida sunshine.
  • Well-maintained picnic areas and outdoor dining spaces for alfresco meals with family and friends.
  • Beautifully landscaped gardens or lawns perfect for relaxing or outdoor activities.
  • Convenient outdoor grilling stations to prepare fresh seafood and local cuisine.
  • Waterfront decks or patios that offer scenic views of the surrounding waters.
  • Secure boat docks or slips for easy access to watercraft adventures in the area.
  • Outdoor recreation facilities such as tennis courts or volleyball courts to stay active during your stay.

Top Attractions Around Toll Gate Shores

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as fishing, kayaking, and exploring nearby parks, making it an ideal destination for those seeking to experience the natural beauty and relaxed vibe of Islamorada.

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Family Activities

  • Fishing Charters: Experience an exciting day of deep-sea fishing tailored for families in the nearby waters of Islamorada, known as the sportfishing capital of the world.
  • Kayaking and Paddleboarding: Enjoy exploring the calm, shallow waters of the region on a kayak or paddleboard, perfect for family outings in this coastal destination.
  • Visit Local Marine Habitats: Discover the vibrant ecosystems through family-friendly boat tours that showcase the region's unique coral reefs and marine life.
  • Beach Relaxation and Water Activities: Spend quality time on the sandy shores with swimming, sandcastle building, or gentle water activities suitable for all ages here.
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Adult Activities

  • Fishing Charters: Experience world-class fishing opportunities right from the area's shores, where you can join a guided charter to catch local game fish.
  • Snorkeling and Diving: Discover vibrant marine life and coral reefs just offshore, making it an ideal spot for underwater adventures in the region.
  • Kayaking and Paddleboarding: Explore the calm waters and mangrove creeks surrounding this destination, perfect for a relaxing day on the water.
  • Wildlife Watching: Visit nearby parks and reserves to observe diverse bird species and other native wildlife in their natural habitat.

Toll Gate Shores Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local waters: Take advantage of the region’s renowned fishing, boating, and snorkeling opportunities to fully enjoy your stay near Toll Gate Shores.
  • Visit nearby landmarks: Discover the natural beauty and cultural highlights that make this destination a unique getaway within the Florida Keys.
  • Plan outdoor activities: Make the most of the area’s tranquil beaches and scenic parks for relaxing days under the sun or sunset viewing.
  • Utilize local amenities: Leverage the nearby shops, dining options, and recreational facilities to enhance your vacation experience in this part of Florida.

Transportation Options

  • Car Rentals: You can easily access rental car services to explore the area at your own pace, making it convenient to visit local attractions and enjoy the scenic views around Islamorada.
  • Taxi Services: Reliable taxi options are available for quick and hassle-free transportation within this region, perfect for short trips or when crossing town.
  • Public Transit: The area offers convenient public transit routes that help you get around without the need for a personal vehicle, ideal for budget-conscious travelers.
  • Boat Rentals: Given the region's coastal charm, renting a boat provides a unique way to explore nearby waterways and enjoy the marine scenery right from your doorstep.

Local Customs Options

  • Respect for Marine Life: You’ll find that local residents and visitors alike cherish the region’s vibrant marine ecosystem, emphasizing responsible boating and fishing practices to preserve these natural resources.
  • Fishermen’s Traditions: Here, the community values their fishing heritage, often participating in early morning trips and understanding the importance of sustainable catch limits.
  • Casual Waterfront Attire: In this destination, dressing comfortably with a relaxed, coastal style is customary, especially during outdoor dining or beach outings.
  • Celebration of Local Art and Culture: The region takes pride in showcasing its unique art inspired by the surrounding waters, with many galleries and events celebrating local creativity and traditions.

Frequently Asked Questions About Toll Gate Shores?

1. What are the top vacation rentals in Toll Gate Shores?

There are a lot of options in Toll Gate Shores. If you plan on staying in the Toll Gate Shores area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Toll Gate Shores:

2. How many vacation rentals have private pools in Toll Gate Shores?

There are 88 vacation rentals with private pools near Toll Gate Shores. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Toll Gate Shores are best for families?

If you are looking for a family-friendly vacation home in Toll Gate Shores, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Toll Gate Shores:

4. How many Rentbyowner vacation rentals are available in Toll Gate Shores?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 322 in the Toll Gate Shores area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Toll Gate Shores. 

5. What is the cancellation policy for properties in Toll Gate Shores, Islamorada?

The cancellation policy varies by listing. You should review the specific cancellation terms listed on each property’s page or contact the owner directly to understand the applicable conditions.

6. How do I ensure my booking is secure when reserving a vacation rental in Islamorada?

Bookings are secured through verified platforms that offer secure payment options. Always confirm details with the property owner and use the platform’s communication channels to keep your transaction safe.

7. Are there any additional fees or charges I should be aware of when booking in this area?

Additional fees such as cleaning, service charges, or taxes may apply and are typically listed during the booking process. It’s recommended to review the total cost before confirming your reservation.

8. What amenities can I expect from vacation rentals in Islamorada?

Property amenities vary but often include features like private pools, waterfront access, and fully equipped kitchens. Details about available amenities are specified in each listing, so review them carefully.

9. How can I find suitable vacation rentals in Toll Gate Shores that match my travel dates?

Use the search filters on the listing platform to select your preferred dates, number of guests, and desired amenities. If you need assistance, reaching out directly to the property owner can also help ensure availability.

Toll Gate Shores Top Rated Vacation Rentals

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