Discover Your Perfect Diamond Isle Vacation Homes

Best Vacation Homes in Diamond Isle

See More Diamond Isle Vacation Rentals

Diamond Isle Luxury Rentals

See More Diamond Isle Luxury Vacation Rentals
Find More Diamond Isle Villas, Resorts, & Rentals on BedroomVillas

Diamond Isle Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Diamond Isle on PetFriendly.io

Diamond Isle Large Vacation Homes

See More Family Vacation Rentals in Diamond Isle on FVR

Why Choose Rent By Owner for your Diamond Isle Vacation Rental Homes?

What makes our Vacation Rentals special?

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

Popular Areas for Diamond Isle Vacation Rentals

Where are the best neighborhoods to stay in Diamond Isle?

When exploring accommodations in Diamond Isle, Clearwater Beach, Florida, you’ll find a variety of neighborhoods that cater to different vacation styles. Staying along the waterfront provides stunning views and easy access to the beach, making it ideal for relaxation and outdoor activities. Alternatively, the nearby residential areas offer a more tranquil setting, perfect for those seeking peace and privacy during their visit. No matter your preference, selecting a neighborhood in this vibrant coastal destination ensures you enjoy the best of Clearwater Beach’s natural beauty and welcoming community, all within reach of local attractions and amenities.

Island Estate

Nestled within the tranquil surroundings of Clearwater Beach, this neighborhood offers a serene setting perfect for relaxing getaways. Here, you can enjoy easy access to the region's beautiful shoreline while experiencing the comfort of well-appointed vacation rentals.

View 36+ Rentals in Island Estate

Best Times to Visit Diamond Isle

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit this destination ensures you can enjoy its pristine beaches and vibrant atmosphere at their best, making your experience in Clearwater Beach truly unforgettable.

Peak Season Highlights

spring
Spring (March to May)

This is a popular time when many travelers visit the area for warm weather and blooming natural beauty, making it ideal for securing your preferred vacation rental.

Average Temperature Daytime: 75°F - Nighttime: 60°F
summer
Summer (June to August)

The peak summer months see increased visitors seeking sunny days and beach activities, so early booking of your vacation rental ensures you enjoy the vibrant coastal atmosphere.

Average Temperature Daytime: 88°F - Nighttime: 75°F

Off-Season Highlights

image
Fall (September to November)

During this quieter season, you can find more availability and better rates on vacation rentals while still enjoying mild weather and calmer beaches.

Average Temperature Daytime: 80°F - Nighttime: 65°F
image
Winter (December to February)

The cooler months attract fewer visitors, offering an excellent opportunity to book your vacation rental at favorable prices and enjoy tranquil surroundings.

Average Temperature Daytime: 65°F - Nighttime: 50°F

Weekly Weather Forecast for Diamond Isle

How to Book Your Diamond Isle 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 Diamond Isle

More Top-Rated Vacation Rentals in Diamond Isle 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

  • Enjoy a private outdoor pool for relaxing swims under the sun.
  • Access to well-maintained outdoor patios or decks ideal for dining and lounging.
  • Take advantage of lush landscaped gardens that add to the scenic appeal of your stay.
  • Benefit from beachfront access points, allowing you to explore the pristine shoreline easily.
  • Use outdoor grilling facilities to prepare delicious meals with family and friends.
  • Relax in shaded cabanas or gazebo areas for a restful retreat in the open air.
  • Participate in water sports activities such as kayaking or paddleboarding right outside your door.

Top Attractions Around Diamond Isle

What attractions are nearby?

Here, you can enjoy a variety of nearby activities, from relaxing on pristine beaches to exploring local watersports, all conveniently close to your vacation rental in the Clearwater Beach area.

image
image

Family Activities

  • Beachfront Family Fun: Spend quality time building sandcastles and swimming in the calm waters along Clearwater Beach, perfect for families seeking a relaxing day by the sea.
  • Clearwater Marine Aquarium: Discover engaging marine life exhibits and rescue stories at this popular attraction, ideal for inspiring young animal lovers.
  • Pier 60 Sunset Celebration: Enjoy an evening of street performers, artisan vendors, and breathtaking sunsets right on the pier, creating memorable moments for all ages.
  • Eco Tour Adventures: Take part in family-friendly eco tours that explore local wildlife and mangroves, providing educational experiences on the region’s natural beauty.
image

Adult Activities

  • Sunset Cruises: Enjoy an evening on the water with a sunset cruise, offering breathtaking views of the Gulf coast and a relaxing experience you'll cherish here.
  • Deep-Sea Fishing: Test your skills and experience the thrill of deep-sea fishing in the region's rich Atlantic waters, perfect for adventure enthusiasts staying nearby.
  • Golfing at Local Courses: Play a round of golf at premier courses renowned in the area, ideal for those seeking leisurely recreation amidst scenic surroundings.
  • Spa and Wellness Centers: Relax and rejuvenate at top-rated spas that utilize the region’s natural therapies, providing ultimate pampering during your stay.

Diamond Isle Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area’s renowned seafood restaurants and waterfront eateries to enjoy authentic flavors of this coastal region.
  • Utilize Water Activities: Make the most of the pristine beaches by engaging in paddleboarding, kayaking, or sunset cruises to fully experience here’s aquatic charm.
  • Visit Less Crowded Beaches: Seek out quieter spots along the shoreline for a relaxing day in the sun away from the busy tourist areas.
  • Plan Outdoor Adventures: Take advantage of nearby parks and nature trails to explore the scenic beauty and enjoy outdoor activities within this destination.

Transportation Options

  • Personal Vehicles: You can easily navigate the area with your own car, enjoying flexible access to local attractions and beaches.
  • Public Transportation: The local bus service provides an affordable and convenient option for exploring here without the need for parking.
  • Taxi and Rideshare Services: Reliable taxi and rideshare options are available to quickly get you to popular spots around this destination.
  • Bicycle Rentals: Biking is a scenic and eco-friendly way to explore close to vacation rentals along the coast and nearby neighborhoods.

Local Customs Options

  • Respect for Local Seafood Traditions: You’ll find that the area values its seafood cuisine, and participating in local dining customs honors the region’s culinary heritage.
  • Greeting with a Friendly Smile: Warm welcomes are customary here, so exchanging friendly gestures helps you connect with residents and enhances your experience.
  • Environmental Conservation Practices: The community takes pride in preserving its natural beauty, encouraging visitors to minimize waste and protect the local environment during their stay.
  • Celebration of Local Festivals: Engaging in regional festivities offers a meaningful way to embrace the area's culture and share in its vibrant community spirit.

Frequently Asked Questions About Diamond Isle?

1. What are the top vacation rentals in Diamond Isle?

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

2. How many vacation rentals have private pools in Diamond Isle?

There are 246 vacation rentals with private pools near Diamond Isle. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Diamond Isle are best for families?

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

4. How many Rentbyowner vacation rentals are available in Diamond Isle?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 3028 in the Diamond Isle 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 Diamond Isle. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property owner and specific listing. It's recommended to review the cancellation terms carefully on the listing page or contact the owner directly for precise details.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning fees, security deposits, or service charges may apply. These details are typically listed during the booking process or can be confirmed by reaching out to the property owner.

7. How do I know if a vacation rental is available for my travel dates?

Availability is shown in real-time on the listing page. If your preferred dates are unavailable, you can often contact the owner to inquire about flexible options or alternative dates.

8. What amenities can I expect at vacation rentals in this destination?

Amenities vary by property but often include essentials like Wi-Fi, parking, air conditioning, and kitchen facilities. For a complete list of amenities, refer to the individual listing description or ask the owner directly.

9. Is it possible to get assistance with issues during my stay?

Support is usually provided through the property owner or the booking platform's customer service. Contact details are shared upon booking, ensuring you have access to help if needed during your stay.

Diamond Isle Top Rated Vacation Rentals

See More Diamond Isle Vacation Rentals