1343+ Perfect Pickle Stays with Nearby Pickleball Facilities |
Windsor Park pickleball Stays, Resort Rentals, & Homes
New
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 3.52 mi to center
12 Bedrooms
11 Baths
36 Guests
6300 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
US $2,186/Night
7 Nights - US $15,299
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 3.62 mi to center
12 Bedrooms
11 Baths
36 Guests
10.76 ft²
- Hot Tub
- Fireplace/Heating
- Pool
Balcony/Terrace
US $1,849/Night
7 Nights - US $12,942
Cottage
- St. Petersburg - Clearwater
- ·
- Barrington Hills
- 0.13 mi to center
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
Kitchen
Parking
US $3,059/Night
7 Nights - US $21,415
Condo
- St. Petersburg - Clearwater
- ·
- On Top of The World
- 0.30 mi to center
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $217/Night
7 Nights - US $1,519
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.63 mi to center
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
1151.74 ft²
Oceanfront
Spa- Fireplace/Heating
Ocean View
US $173/Night
7 Nights - US $1,211
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.36 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1585 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
View
US $194/Night
7 Nights - US $1,361
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 3.83 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1270 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $258/Night
7 Nights - US $1,806
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.64 mi to center
3 Bedrooms
2 Baths
2 Guests
1244 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $194/Night
7 Nights - US $1,361
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.35 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
Air Conditioner
US $176/Night
7 Nights - US $1,230
Luxury Places to Stay in Windsor Park
Over 1334+ Luxury Places to Stay in or Near Windsor Park
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.14 mi to center
1 Bedroom
1 Bath
2 Guests
Pet Friendly- Parking
- Air Conditioner
Internet
US $1,871/Night
7 Nights - US $13,098
House
- St. Petersburg - Clearwater
- ·
- Barrington Hills
- 0.13 mi to center
1 Bedroom
3 Baths
6 Guests
1786.81 ft²
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $1,539/Night
7 Nights - US $10,771
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.08 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
4 Baths
16 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,528/Night
7 Nights - US $10,698
Apartment
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.42 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Parking
- Air Conditioner
US $1,355/Night
7 Nights - US $9,486
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.87 mi to center
7 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,354/Night
7 Nights - US $9,476
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 1.68 mi to center
5 Bedrooms
3 Baths
10 Guests
2098.96 ft²
- Spa
- Fireplace/Heating
- Parking
- Internet
US $1,324/Night
7 Nights - US $9,268
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.86 mi to center
8 Bedrooms
6 Baths
26 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,316/Night
7 Nights - US $9,211
Villa
- St. Petersburg - Clearwater
- ·
- Dunedin
- 2.10 mi to center
10.0Exceptional
(11 Reviews)
7 Bedrooms
5 Baths
18 Guests
6500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $1,268/Night
7 Nights - US $8,875
House
- St. Petersburg - Clearwater
- ·
- On Top of The World
- 0.36 mi to center
5 Bedrooms
3 Baths
10 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,111/Night
7 Nights - US $7,778
Top-Rated Villas with a Pool in Windsor Park
Over 385+ Top-Rated Private Villas with a Pool in or Near Windsor Park
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.17 mi to center
10.0Exceptional
(119 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $238/Night
7 Nights - US $1,668
Cottage
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.78 mi to center
10.0Exceptional
(70 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $207/Night
7 Nights - US $1,448
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.38 mi to center
10.0Exceptional
(61 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $482/Night
7 Nights - US $3,375
Apartment
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.97 mi to center
10.0Exceptional
(58 Reviews)
1 Bedroom
1 Bath
3 Guests
325 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $244/Night
7 Nights - US $1,706
Cottage
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.65 mi to center
10.0Exceptional
(50 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $199/Night
7 Nights - US $1,391
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 2.32 mi to center
10.0Exceptional
(46 Reviews)
3 Bedrooms
2 Baths
8 Guests
1500 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $368/Night
7 Nights - US $2,573
Condo
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.38 mi to center
10.0Exceptional
(43 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $357/Night
7 Nights - US $2,498
Condo
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.19 mi to center
10.0Exceptional
(43 Reviews)
1 Bedroom
1 Bath
4 Guests
730 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $143/Night
7 Nights - US $1,000
Apartment
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.16 mi to center
10.0Exceptional
(40 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $222/Night
7 Nights - US $1,551
Pet-Friendly Villas in Windsor Park
Over 551+ Pet-Friendly Private Villas in or Near Windsor Park
New
Condo
- St. Petersburg - Clearwater
- ·
- On Top of The World
- 0.32 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $471/Night
7 Nights - US $3,300
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.77 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1367.02 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,732
Hotel
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.08 mi to center
9.4Exceptional
(277 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $172/Night
7 Nights - US $1,203
New
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 3.33 mi to center
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $401/Night
7 Nights - US $2,808
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.27 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1130.21 ft²
- Oceanfront
- Hot Tub
- Spa
Skiing
US $269/Night
7 Nights - US $1,883
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 1.72 mi to center
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $143/Night
7 Nights - US $999
New
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.92 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $88/Night
7 Nights - US $616
Cottage
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.14 mi to center
10.0Exceptional
(79 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,540
Cottage
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.14 mi to center
10.0Exceptional
(63 Reviews)
1 Bedroom
1 Bath
4 Guests
480 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,543
Large Private Villas in Windsor Park
Over 140+ Large Villas in or Near Windsor Park for Groups and Families
Villa
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.82 mi to center
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $219/Night
7 Nights - US $1,533
New
Villa
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.91 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
850.35 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $189/Night
7 Nights - US $1,323
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.94 mi to center
10.0Exceptional
(36 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $402/Night
7 Nights - US $2,811
Bed & Breakfast
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.13 mi to center
9.3Exceptional
(142 Reviews)
11 Bedrooms
9 Baths
22 Guests
542.98 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $250/Night
7 Nights - US $1,750
House
- St. Petersburg - Clearwater
- ·
- Barrington Hills
- 0.14 mi to center
10.0Exceptional
(26 Reviews)
5 Bedrooms
3 Baths
10 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $632/Night
7 Nights - US $4,422
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.61 mi to center
10.0Exceptional
(21 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $338/Night
7 Nights - US $2,365
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.59 mi to center
10.0Exceptional
(21 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,740
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.00 mi to center
10.0Exceptional
(14 Reviews)
4 Bedrooms
2 Baths
12 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $568/Night
7 Nights - US $3,979
Villa
- St. Petersburg - Clearwater
- ·
- Dunedin
- 2.00 mi to center
10.0Exceptional
(12 Reviews)
8 Bedrooms
7 Baths
16 Guests
10000 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $832/Night
7 Nights - US $5,826
Wheelchair Accessible Holiday Homes in Windsor Park
Over 72+ Wheelchair Accessible Villas and Holiday Homes in or Near Windsor Park
Condo
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.18 mi to center
10.0Exceptional
(287 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $299/Night
7 Nights - US $2,096
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.05 mi to center
9.0Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
10 Guests
1399.31 ft²
- Oceanfront
- Skiing
- Fireplace/Heating
- Ocean View
US $246/Night
7 Nights - US $1,721
Apartment
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.99 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $509/Night
7 Nights - US $3,565
Condo
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.16 mi to center
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $129/Night
7 Nights - US $906
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.04 mi to center
8.5Fabulous
(16 Reviews)
4 Bedrooms
3 Baths
10 Guests
2098.96 ft²
- Oceanfront
- Spa
- Skiing
- Fireplace/Heating
US $398/Night
7 Nights - US $2,788
Apartment
- St. Petersburg - Clearwater
- ·
- Dunedin
- 0.99 mi to center
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $217/Night
7 Nights - US $1,521
Condo
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.32 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1241 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $95/Night
7 Nights - US $663
Condo
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.15 mi to center
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $179/Night
7 Nights - US $1,251
Condo
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.00 mi to center
9.6Exceptional
(91 Reviews)
1 Bedroom
1 Bath
3 Guests
350 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $186/Night
7 Nights - US $1,305
Windsor Park Villas, Airbnb and Holiday Homes Under $200
Over 690+ Windsor Park Private Villas, Airbnb and Holiday Homes Under $200
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.46 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $190/Night
7 Nights - US $1,328
House
- St. Petersburg - Clearwater
- ·
- Clearwater
- 4.32 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1237.85 ft²
- Fireplace/Heating
- Parking
- Internet
Child Friendly
US $136/Night
7 Nights - US $952
Hotel
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.14 mi to center
9.8Exceptional
(297 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
US $172/Night
7 Nights - US $1,204
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.61 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $149/Night
7 Nights - US $1,043
Apartment
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.10 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
796.53 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $180/Night
7 Nights - US $1,260
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.36 mi to center
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $147/Night
7 Nights - US $1,027
Cabin
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.44 mi to center
1 Bedroom
1 Bath
1 Guest
240 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $67/Night
7 Nights - US $467
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.40 mi to center
1 Bedroom
1 Bath
1 Guest
140 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $61/Night
7 Nights - US $427
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 2.44 mi to center
1 Bedroom
1 Bath
1 Guest
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $61/Night
7 Nights - US $427
Instantly Bookable Villa Rentals in Windsor Park
Over 821+ Instantly Bookable Private Villas in or Near Windsor Park
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.45 mi to center
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $226/Night
7 Nights - US $1,582
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.06 mi to center
1 Bedroom
1 Bath
4 Guests
333.68 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $147/Night
7 Nights - US $1,029
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.25 mi to center
9.4Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $263/Night
7 Nights - US $1,841
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.38 mi to center
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $224/Night
7 Nights - US $1,571
New
Apartment
- St. Petersburg - Clearwater
- ·
- Clearwater
- 5.27 mi to center
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $216/Night
7 Nights - US $1,514
House
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.93 mi to center
10.0Exceptional
(123 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $178/Night
7 Nights - US $1,248
Apartment
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.16 mi to center
10.0Exceptional
(59 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $223/Night
7 Nights - US $1,558
Cottage
- St. Petersburg - Clearwater
- ·
- Dunedin
- 1.98 mi to center
10.0Exceptional
(56 Reviews)
2 Bedrooms
2 Baths
5 Guests
1100 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $211/Night
7 Nights - US $1,480
Apartment
- St. Petersburg - Clearwater
- ·
- Downtown Dunedin
- 0.16 mi to center
10.0Exceptional
(53 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $220/Night
7 Nights - US $1,540
Book a Last Minute Place to Stay in Windsor Park
About Windsor Park Vacation Rentals
Discover over 1343 amazing vacation rental options in Windsor Park with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Windsor Park.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 590.98 ft², with prices averaging US $251 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Windsor Park.
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Top Pickleball-Ready Accommodation Types in Windsor Park
| Type | Count |
|---|---|
| Vacation Homes | 757 |
| Holiday Apartments | 339 |
| Cottages | 59 |
| Villas | 20 |
Use these Quick Filters to Find a Vacation Rental in Windsor Park
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Windsor Park with PickleTrip™.
Weather in Windsor Park, FL
View the weather forecast for Windsor Park before booking your Windsor Park Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Windsor Park?
What are the top vacation rentals, resorts, and hotels in Windsor Park with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Windsor Park. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Windsor Park!
- Minutes from Honeymoon Island/Clearwater beaches. Walk or bike to town.
- Home in Clearwater
- Sleeps36 2Homes 12BR Heated Pool Spa Pickleball 14+ Parking
- Sleeps36 2Homes 12BR Heated Pool Spa Pickleball 14 Parking
- Clearwater condo with lots of ammenities! 55+ plus community
- Furnished house in Dunedin. Canal view. Close to Downtown, Beaches & Stadiums
- Downtown Dunedin Walking District
- Coastal Dunedin with GOLF CART!
- The Cove - House with a Private Pool and Bikes!
- Classy & Clean Pet Friendly
How many pickleball-ready properties have private pools in Windsor Park?
Discover 147 accommodations with private or nearby pickleball courts in Windsor Park. Some of the best destinations to stay and play pickleball are:
- Charming Clearwater Family Home w pool
- Howard Johnson by Wyndham Clearwater - Dunedin
- Beso Del Sol Resort
- Private Heated Salt Water Pool Oasis 10 Mins to Clearwater Beach
Which vacation rentals, resorts, or hotels in Windsor Park is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Windsor Park? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- BlueJay's Nest: 2 units w/shared yard! - Duplex - Walk to Water and Stadium
- The Rooftop of Dunedin
- Residence Inn by Marriott Clearwater Downtown
How many PickleTrip vacation rentals or resorts are available in Windsor Park?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 1343 properties listed in Windsor Park in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Windsor Woods Vacation Rentals in Florida | 1306 |
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