Best Vacation Homes in On Top of The World
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Security/Safety
- Wellness Facilities
On Top of The World Luxury Rentals
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Pet Friendly
- Security/Safety
On Top of The World Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
On Top of The World Large Vacation Homes
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
Why Choose Rent By Owner for your On Top of The World Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for On Top of The World Vacation Rentals
Where are the best neighborhoods to stay in On Top of The World?
When choosing where to stay in On Top of The World, Clearwater, Florida, you’ll find a variety of neighborhoods that offer both convenience and a welcoming atmosphere. This vibrant community provides easy access to local amenities and scenic surroundings, making it an ideal destination for your next getaway. Whether you prefer a quiet retreat or a lively locale, the neighborhood options here are tailored to suit different travel styles. Booking your vacation rentals in this area ensures a comfortable and memorable experience, supported by the dependable and seamless service offered by trusted accommodation providers.
Woodgate
In this charming neighborhood, you can enjoy a tranquil setting while remaining close to the area's beaches and attractions. It’s an ideal choice for those seeking comfortable vacation rentals in a peaceful part of Clearwater.
View 772+ Rentals in WoodgateBest Times to Visit On Top of The World
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you enjoy the best weather and local experiences when booking vacation rentals in this popular destination on Florida’s Gulf Coast.
Peak Season Highlights
Spring (March to May)
During this time, you can enjoy warm weather and abundant sunshine, making it ideal for outdoor activities and exploring the region's natural beauty.
Winter Holidays (December to February)
This period offers cooler temperatures with a pleasant escape from colder northern climates, perfect for relaxing in comfortable vacation rentals while experiencing mild coastal weather.
Off-Season Highlights
Summer (June to August)
While the summer months bring higher temperatures, they also offer fewer crowds and more availability in rental properties, ideal for travelers seeking tranquility.
Fall (September to November)
During this shoulder season, you’ll find less humidity and moderate temperatures, providing a comfortable climate for enjoying the area’s peaceful ambiance without the peak-season rush.
Weekly Weather Forecast for On Top of The World
How to Book Your On Top of The World Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in On Top of The World
Common Vacation Rentals Amenities
What amenities can you expect?
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 access to well-maintained outdoor swimming pools within the community.
- Take advantage of lush, landscaped gardens and walking trails for outdoor strolling.
- Relish in the use of tennis courts available for your active recreation.
- Make the most of outdoor barbecue areas perfect for social gatherings.
- Experience the convenience of on-site fitness facilities with outdoor workout spaces.
- Explore nearby parks and nature preserves ideal for outdoor adventures.
- Utilize outdoor seating areas designed for relaxation and enjoying the Florida sunshine.
Top Attractions Around On Top of The World
What attractions are nearby?
Within the area, you can enjoy a variety of outdoor activities and scenic spots that highlight the natural beauty of this destination, providing a perfect backdrop for your memorable stay.
Family Activities
- Clearwater Marine Aquarium Visit: Discover local marine life and enjoy interactive exhibits that are perfect for a family day in this coastal region.
- Beach Day at Clearwater Beach: Relax and have fun on the soft sands, swimming in the gentle waves of this popular destination along the Gulf Coast.
- Fishing Charters and Sunset Cruises: Experience the thrill of fishing or enjoy scenic boat rides that showcase the area's stunning coastline.
- Pier 60 Park Activities: Enjoy playgrounds, live entertainment, and beautiful sunset views at this waterfront park suitable for all ages.
Adult Activities
- Golfing at the Local Courses: Enjoy a round of golf at nearby courses that offer scenic views and challenging fairways, perfect for adults seeking relaxation and recreation in the area.
- Spa and Wellness Centers: Indulge in rejuvenating treatments and massages at local spas to unwind and enhance your vacation experience here in this vibrant destination.
- Dining Experiences: Explore a variety of restaurants and cafes that showcase the region’s flavorful cuisine, making every meal an enjoyable part of your getaway.
- Shopping at Coastal Boutiques: Discover unique shops and boutiques in the area, offering everything from beachwear to souvenirs, ideal for leisurely afternoons during your stay.
Other Places to Stay in On Top of The World, FL
On Top of The World Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Review the area's event calendar to align your stay with local festivals or activities, enhancing your experience in Clearwater.
- Explore Nearby Beaches: Take advantage of the region’s beautiful coastline by scheduling visits to popular beaches close to your vacation rental for relaxing days in the sun.
- Utilize Local Amenities: Make the most of community amenities like pools, clubs, or fitness centers available within this destination to enjoy a comfortable and engaging stay.
- Discover Authentic Dining: Seek out local restaurants and eateries nearby to savor regional flavors and create memorable culinary experiences during your visit here.
Transportation Options
- Personal Vehicles: Renting or using your own car offers the most flexibility to explore all that the area around On Top of The World has to offer at your own pace.
- Public Transit: Local bus services provide an affordable and convenient way to navigate the region without the need for a car, especially when visiting nearby attractions.
- Taxi Services: Taxis and ride-share options such as Uber and Lyft are readily available for quick, hassle-free transportation within the vicinity.
- Rental Bikes and Scooters: For short trips or exploring scenic areas in this destination, bike and scooter rentals are an eco-friendly alternative that adds convenience to your stay.
Local Customs Options
- Florida Friendly Landscaping: Locals here prioritize environmentally conscious gardening practices that conserve water and promote native plant growth, reflecting the region's commitment to sustainability.
- Seafood Dining Customs: Enjoying fresh seafood is a common tradition in this area, with locals often gathering for casual meals that celebrate the region's abundant marine resources.
- Community Events and Festivals: Frequent neighborhood gatherings and seasonal festivals foster a close-knit atmosphere, highlighting the region’s vibrant local culture.
- Respect for Nature and Wildlife: Visitors are encouraged to observe wildlife respectfully and adhere to conservation efforts, as preserving the area's natural beauty is a valued custom here.
Frequently Asked Questions About On Top of The World?
1. What are the top vacation rentals in On Top of The World?
There are a lot of options in On Top of The World. If you plan on staying in the On Top of The World area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in On Top of The World:
- Downtown Dunedin Walking District
- The Villa at Harbor House
- Key West Style Waterfront, Private Pool, WiFi, Close to Village & Beaches Pet OK
- Villa Italia "Villas by Christine"
- The Cove - Bungalow with a Private Pool and Bikes!
- Waterfront Home - Luxury Relaxation - Heart of Safety Harbor
- Coastal Downtown Dunedin w/GOLF CART!
- Classy & Clean Pet Friendly
- AMAZING LARGE VACATION HEATED POOL & HOT TUB HOME DUNEDIN CLEARWATER!
- Cozy creative getaway guesthouse
2. How many vacation rentals have private pools in On Top of The World?
There are 124 vacation rentals with private pools near On Top of The World. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in On Top of The World are best for families?
If you are looking for a family-friendly vacation home in On Top of The World, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in On Top of The World:
4. How many Rentbyowner vacation rentals are available in On Top of The World?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 841 in the On Top of The World 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 On Top of The World.
On Top of The World Top Rated Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
