Best Vacation Homes in Windsor Park
New
House
2 Bedrooms
2 Baths
6 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Air Conditioner
R4,082/Night
7 Nights - R28,568
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1151.74 ft²
Oceanfront
Spa- Fireplace/Heating
Ocean View
R2,805/Night
7 Nights - R19,635
R48,807/Night
7 Nights - R341,650
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R3,874/Night
7 Nights - R27,109
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1367.02 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,327/Night
7 Nights - R44,295
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
R3,223/Night
7 Nights - R22,553
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R2,784/Night
7 Nights - R19,489
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,684/Night
7 Nights - R18,791
Windsor Park Luxury Rentals
New
House
12 Bedrooms
11 Baths
36 Guests
6300 ft²
Private Pool
Hot Tub- Fireplace/Heating
Pool
R33,948/Night
7 Nights - R237,641
Apartment
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Parking
- Air Conditioner
Internet
R30,337/Night
7 Nights - R212,364
House
12 Bedrooms
11 Baths
36 Guests
10.76 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R29,976/Night
7 Nights - R209,835
House
1 Bedroom
3 Baths
6 Guests
1786.81 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
R24,948/Night
7 Nights - R174,635
House
10.0(1 Review)
6 Bedrooms
4 Baths
16 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R24,611/Night
7 Nights - R172,284
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
R21,971/Night
7 Nights - R153,801
House
8 Bedrooms
6 Baths
26 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R21,334/Night
7 Nights - R149,342
House
7 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R20,502/Night
7 Nights - R143,522
Windsor Park Pet Friendly Vacation Rentals
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
R2,683/Night
7 Nights - R18,775
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1130.21 ft²
- Oceanfront
- Hot Tub
- Spa
Skiing
R4,361/Night
7 Nights - R30,530
Hotel
9.4(279 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,464/Night
7 Nights - R24,239
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,658/Night
7 Nights - R18,597
House
9.2(13 Reviews)
3 Bedrooms
3 Baths
8 Guests
1550 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Pet Friendly
R4,815/Night
7 Nights - R33,708
New
Apartment
1 Bedroom
1 Bath
4 Guests
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
R2,628/Night
7 Nights - R18,402
House
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,942/Night
7 Nights - R13,587
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R1,631/Night
7 Nights - R11,414
Windsor Park Large Vacation Homes
Villa
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R3,550/Night
7 Nights - R24,855
New
Villa
10.0(1 Review)
2 Bedrooms
1 Bath
5 Guests
850.35 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R3,063/Night
7 Nights - R21,450
House
10.0(36 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R6,511/Night
7 Nights - R45,576
Bed & Breakfast
9.3(142 Reviews)
11 Bedrooms
9 Baths
22 Guests
542.98 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
R4,053/Night
7 Nights - R28,374
House
10.0(34 Reviews)
4 Bedrooms
2 Baths
13 Guests
2217 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R6,086/Night
7 Nights - R42,593
House
10.0(26 Reviews)
5 Bedrooms
3 Baths
10 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R10,242/Night
7 Nights - R71,696
House
10.0(21 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
R5,478/Night
7 Nights - R38,345
House
10.0(21 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R4,031/Night
7 Nights - R28,211
Why Choose Rent By Owner for your Windsor Park Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Windsor Park Vacation Rentals
Where are the best neighborhoods to stay in Windsor Park?
Windsor Park in Clearwater, Florida, offers a charming and peaceful neighborhood setting for your next getaway. Located conveniently within the city, this area provides easy access to local attractions while maintaining a quiet residential atmosphere. Whether you're seeking a relaxing retreat or exploring nearby beaches and parks, Windsor Park's prime location makes it an ideal base for your vacation. Booking a vacation rental here ensures a comfortable and trustworthy stay in one of Clearwater's most desirable neighborhoods, giving you the confidence to enjoy your visit to Florida to the fullest.
Windsor Woods
This neighborhood offers a tranquil setting close to Clearwater’s popular attractions, making it an ideal choice for those seeking a peaceful retreat. Here, you can enjoy the comfort of well-maintained vacation rentals in a welcoming community.
View 1306+ Rentals in Windsor WoodsBest Times to Visit Windsor Park
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here ensures you experience the region's pleasant weather and ideal conditions for your getaway, making it the perfect setting for your vacation rentals in Windsor Park, Clearwater, Florida, USA.
Peak Season Highlights
Spring (March to May)
During the spring months, this destination offers pleasant weather with warm daytime temperatures, making it ideal for outdoor activities and exploring the area’s natural beauty. It’s a popular time for visitors seeking comfortable conditions and vibrant scenery.
Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
Winter Holidays (December to February)
The winter season attracts travelers looking to escape colder climates, enjoying mild temperatures and sunny days. This period is perfect for relaxing in your vacation rental while taking advantage of the region’s festive atmosphere.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Summer (June to August)
While summer might be warmer, it’s also less crowded, offering a more relaxed experience here. You can enjoy longer daylight hours and savings on your vacation rentals during this off-peak time.
Average Temperature Daytime: 85-90°F - Nighttime: 70-75°F
Fall (September to November)
Autumn brings cooler temperatures and fewer visitors, providing a peaceful setting to unwind. This period is ideal for those who prefer avoiding the peak travel crowds while still experiencing pleasant weather.
Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
Weekly Weather Forecast for Windsor Park
How to Book Your Windsor Park 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 Windsor Park
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 outdoor seating areas perfect for relaxing and dining under the sun in this sunny region.
- Take advantage of a private backyard with lush landscaping, ideal for outdoor gatherings or quiet walks.
- Make use of a swimming pool to cool off during warm Florida days in this popular area.
- Utilize a barbecue grill to host cookouts while soaking up the pleasant climate of the region.
- Benefit from shaded patios or verandas, providing comfortable spots to unwind outdoors.
- Access nearby parks or green spaces that are often included as part of the outdoor amenities in this destination.
- Leisurely stroll along landscaped gardens or pathways designed for outdoor enjoyment here in Clearwater’s scenic surroundings.
Top Attractions Around Windsor Park
What attractions are nearby?
Enjoy a variety of outdoor activities and water-based adventures just moments from your stay, making this destination perfect for exploring the region’s beautiful parks and scenic coastal areas.
Family Activities
- Windsor Park Community Pool: Enjoy a refreshing dip and relaxing hours at the community pool, perfect for family fun in the sun.
- Windsor Park Playground: Let the kids burn off some energy on the playground equipment set amidst lush surroundings in this family-friendly area.
- Windsor Park Nature Trails: Take a scenic walk or bike ride along the nature trails to explore the local flora and fauna with loved ones.
- Nearby Clearwater Beach: Spend a memorable day building sandcastles and soaking up sunshine at the beautiful beaches just a short drive away from here.
Adult Activities
- Golfing at the Clearwater Country Club: Enjoy a round of golf on pristine greens just a short drive from your vacation rental in the area.
- Exploring local art galleries and studios: Immerse yourself in the region's vibrant arts scene by visiting nearby galleries that showcase talented regional artists.
- Enjoying waterfront dining experiences: Savor fresh seafood and local cuisine at popular restaurants along the coast, offering stunning water views.
- Visiting parks and nature preserves: Take a relaxing walk or hike through scenic outdoor spaces to experience the natural beauty that defines this destination.
Windsor Park Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take advantage of the area's local attractions and events by planning ahead to maximize your time and experience in this popular Florida destination.
- Choose a Prime Location: Select a vacation rental that is conveniently situated near key beaches, parks, or dining options to make exploring here effortless and enjoyable.
- Utilize Local Tips and Resources: Engage with the community or your host to discover hidden gems and insider recommendations for truly authentic experiences in the region.
- Pack Smart and Light: Bring only essentials suited for the warm climate and outdoor activities common here to stay comfortable during your visit.
Transportation Options
- Rental Car Services: Major providers like Enterprise and Hertz operate nearby, offering convenient transportation options for exploring the region at your own pace.
- Public Transit: The local transit system provides reliable bus routes that connect Windsor Park to Clearwater's key attractions and facilities in the area.
- Taxi and Rideshare: Taxis and rideshare services such as Uber and Lyft are readily available, making it easy to reach local beaches, dining options, and entertainment venues.
- Bicycle Rentals: For a more active approach, several bike rental shops offer affordable options to explore the scenic surroundings of this destination comfortably and environmentally friendly.
Local Customs Options
- Greeting Etiquette: Locals here often greet visitors with a friendly smile and a casual hello, reflecting the warm hospitality of this coastal region.
- Beach Customs: It's customary to show respect for the local environment by cleaning up after yourself and adhering to designated swimming and boating areas.
- Food Traditions: Sharing seafood dishes and participating in casual beachside cookouts are common ways to experience the culinary culture of this area.
- Festive Celebrations: Attending community events and holiday celebrations, such as the Fourth of July, offers a glimpse into the region's lively and patriotic spirit.
Frequently Asked Questions About Windsor Park?
1. What are the top vacation rentals in Windsor Park?
There are a lot of options in Windsor Park. If you plan on staying in the Windsor Park area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor Park:
- Downtown Dunedin Walking District
- Coastal Dunedin with GOLF CART!
- The Cove - House with a Private Pool and Bikes!
- Classy & Clean Pet Friendly
- Downtown Dunedin Cottage Walk to Restaurants
- Designer Home for 8 Walk to Downtown Dunedin and Waterfront Pets Ok
- Cozy and roomy cottage
- Stay in Downtown Dunedin Walk Everywhere
- Condor Nest-private home-walk to downtown & the water! nNew heated POOL!
- The Heart of Downtown Dunedin on Main St
2. How many vacation rentals have private pools in Windsor Park?
There are 151 vacation rentals with private pools near Windsor Park. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor Park are best for families?
If you are looking for a family-friendly vacation home in Windsor Park, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor Park:
4. How many Rentbyowner vacation rentals are available in Windsor Park?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1326 in the Windsor Park 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 Windsor Park.
5. What is the cancellation policy for vacation rentals in Windsor Park, Clearwater?
Cancellation policies can vary depending on the host and specific property listing. It’s important to review the individual rental agreement for details on cancellations, refunds, and any applicable fees before booking.
6. How do I find available dates and book a vacation rental in Windsor Park?
You can easily check availability and make reservations through the property’s listing page. Simply select your desired dates, review the details, and proceed with the secure booking process.
7. Are there any specific house rules or amenities I should know about when staying in this area?
Each rental listing provides detailed information on house rules and amenities offered. Be sure to read the description carefully to ensure it meets your needs and expectations during your stay.
8. What should I do if I encounter issues during my stay at a rental in this destination?
For any concerns or issues, contact the property owner or manager directly through the messaging platform provided. For further assistance, customer support services are also available to help resolve your concerns.
9. Is there any additional fee or deposit required when booking vacation rentals here?
Additional fees or deposits, such as security deposits or cleaning fees, are specified in the listing details. It’s advisable to review these before confirming your reservation to avoid surprises.
Windsor Park Top Rated Vacation Rentals
House
10.0(119 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R3,863/Night
7 Nights - R27,044
Cottage
10.0(70 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
R3,353/Night
7 Nights - R23,477
House
10.0(61 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R7,817/Night
7 Nights - R54,720
Apartment
10.0(58 Reviews)
1 Bedroom
1 Bath
3 Guests
325 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R3,952/Night
7 Nights - R27,660
Cottage
10.0(50 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,221/Night
7 Nights - R22,553
House
10.0(46 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R5,960/Night
7 Nights - R41,717
Condo
10.0(44 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
R5,786/Night
7 Nights - R40,501
Apartment
10.0(40 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
R3,592/Night
7 Nights - R25,147
