Windsor pickleball Stays, Resort Rentals, & Homes
Villa
- Jamaica
- ·
- Silver Sands
- 0.12 mi to center
5 Bedrooms
5 Baths
12 Guests
Private Pool
Oceanfront
Pool
Ocean View
US $1,200/Night
7 Nights - US $8,400
House
- Montego Bay
- ·
- Falmouth
- 1.98 mi to center
10.0Exceptional
(7 Reviews)
5 Bedrooms
4 Baths
10 Guests
15230.93 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
US $123/Night
7 Nights - US $861
Resort
- Montego Bay
- ·
- Falmouth
- 1.08 mi to center
10.0Exceptional
(2 Reviews)
1 Bath
Hot Tub
Spa- Pool
- Balcony/Terrace
US $3,779/Night
7 Nights - US $26,453
House
- Jamaica
- ·
- Silver Sands
- 0.57 mi to center
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $529/Night
7 Nights - US $3,703
House
- Montego Bay
- ·
- Falmouth
- 2.25 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
5 Guests
1097.92 ft²
- Pool
- Balcony/Terrace
Parking
Air Conditioner
US $130/Night
7 Nights - US $910
Villa
- Jamaica
- ·
- Silver Sands
- 0.38 mi to center
10.0Exceptional
(16 Reviews)
3 Bedrooms
1 Bath
7 Guests
1650 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $400/Night
7 Nights - US $2,800
House
- Montego Bay
- ·
- Falmouth
- 0.18 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
Kitchen- Parking
- Air Conditioner
US $88/Night
7 Nights - US $619
House
- Montego Bay
- ·
- Falmouth
- 2.55 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $117/Night
7 Nights - US $818
House
- Montego Bay
- ·
- Duncans
- 0.95 mi to center
10.0Exceptional
(8 Reviews)
7 Bedrooms
7 Baths
16 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $845/Night
7 Nights - US $5,915
Luxury Places to Stay in Windsor
Over 446+ Luxury Places to Stay in or Near Windsor
Resort
- Montego Bay
- ·
- Falmouth
- 2.90 mi to center
7.6Very Good
(271 Reviews)
18 Baths
39 Guests
857.52 ft²
Private Beach- Oceanfront
- Spa
- Pool
US $2,670/Night
7 Nights - US $18,690
Villa
10.0Exceptional
(6 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,843/Night
7 Nights - US $12,898
Villa
- Jamaica
- ·
- Silver Sands
- 0.33 mi to center
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $1,645/Night
7 Nights - US $11,515
Villa
- Jamaica
- ·
- Silver Sands
- 0.26 mi to center
5 Bedrooms
5 Baths
12 Guests
2690.98 ft²
- Hot Tub
- Pool
- Balcony/Terrace
Breakfast
US $1,600/Night
7 Nights - US $11,200
Villa
- Montego Bay
- ·
- Duncans
- 0.94 mi to center
5 Bedrooms
5 Baths
12 Guests
- Private Pool
- Oceanfront
- Hot Tub
Fireplace/Heating
US $1,573/Night
7 Nights - US $11,011
Villa
- Montego Bay
- ·
- Greenwood
- 0.17 mi to center
10.0Exceptional
(3 Reviews)
8 Bedrooms
10 Baths
16 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,548/Night
7 Nights - US $10,833
House
- Jamaica
- ·
- Silver Sands
- 0.27 mi to center
10.0Exceptional
(1 Review)
7 Bedrooms
7 Baths
14 Guests
15004.89 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,420/Night
7 Nights - US $9,940
Villa
- Montego Bay
- ·
- Duncans
- 0.84 mi to center
9.6Exceptional
(5 Reviews)
10 Bedrooms
11 Baths
30 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,305/Night
7 Nights - US $9,133
House
- Jamaica
- ·
- Silver Sands
- 0.47 mi to center
7 Bedrooms
7 Baths
14 Guests
15000 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,300/Night
7 Nights - US $9,100
Top-Rated Villas with a Pool in Windsor
Over 193+ Top-Rated Private Villas with a Pool in or Near Windsor
Villa
- Jamaica
- ·
- Silver Sands
- 0.45 mi to center
10.0Exceptional
(7 Reviews)
4 Bedrooms
6 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Kitchen
US $950/Night
7 Nights - US $6,650
House
- Montego Bay
- ·
- Falmouth
- 1.93 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
1269 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $155/Night
7 Nights - US $1,085
House
- Jamaica
- ·
- Silver Sands
- 0.26 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $416/Night
7 Nights - US $2,913
House
- Jamaica
- ·
- Silver Sands
- 0.20 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
4 Baths
6 Guests
2500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $365/Night
7 Nights - US $2,552
House
- Jamaica
- ·
- Silver Sands
- 0.39 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $430/Night
7 Nights - US $3,013
House
- Montego Bay
- ·
- Falmouth
- 2.28 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $174/Night
7 Nights - US $1,215
Villa
- Montego Bay
- ·
- Falmouth
- 1.58 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
6 Baths
12 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $911/Night
7 Nights - US $6,377
House
- Jamaica
- ·
- Silver Sands
- 3.56 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
1827 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,148
House
- Montego Bay
- ·
- Falmouth
- 1.63 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
5 Baths
8 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $612/Night
7 Nights - US $4,284
Pet-Friendly Villas in Windsor
Over 37+ Pet-Friendly Private Villas in or Near Windsor
Villa
- Montego Bay
- ·
- Falmouth
- 2.26 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
3 Baths
10 Guests
1450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $207/Night
7 Nights - US $1,447
House
- Montego Bay
- ·
- Falmouth
- 2.30 mi to center
9.6Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
4 Guests
1302.43 ft²
- Pool
- View
- Breakfast
Pet Friendly
US $86/Night
7 Nights - US $603
House
- Montego Bay
- ·
- Falmouth
- 0.25 mi to center
9.8Exceptional
(19 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $258/Night
7 Nights - US $1,803
Villa
- Montego Bay
- ·
- Falmouth
- 2.76 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
7 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $215/Night
7 Nights - US $1,505
Villa
- Jamaica
- ·
- Silver Sands
- 0.13 mi to center
9.3Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
3003.13 ft²
- Private Beach
- Oceanfront
- Ocean View
- Balcony/Terrace
US $575/Night
7 Nights - US $4,023
Villa
- Montego Bay
- ·
- Falmouth
- 2.26 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
10 Guests
1450 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $213/Night
7 Nights - US $1,492
Villa
- Montego Bay
- ·
- Falmouth
- 0.25 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $147/Night
7 Nights - US $1,031
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $84/Night
7 Nights - US $587
Villa
- Montego Bay
- ·
- Falmouth
- 0.25 mi to center
3 Bedrooms
3 Baths
10 Guests
1450 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $812/Night
7 Nights - US $5,685
Large Private Villas in Windsor
Over 122+ Large Villas in or Near Windsor for Groups and Families
Villa
- Jamaica
- ·
- Silver Sands
- 0.19 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
5 Baths
8 Guests
3600 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,000/Night
7 Nights - US $7,000
Villa
9.7Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
69750.14 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $121/Night
7 Nights - US $849
Villa
- Montego Bay
- ·
- Falmouth
- 2.15 mi to center
9.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
US $285/Night
7 Nights - US $1,993
Villa
- Montego Bay
- ·
- Falmouth
- 0.21 mi to center
10.0Exceptional
(1 Review)
8 Bedrooms
8 Baths
18 Guests
6000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $824/Night
7 Nights - US $5,768
Villa
- Montego Bay
- ·
- Florence Hall Village
- 0.08 mi to center
9.3Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1270.14 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $195/Night
7 Nights - US $1,363
Villa
- Montego Bay
- ·
- Duncans
- 0.85 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
5 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Breakfast
US $800/Night
7 Nights - US $5,600
Villa
- Jamaica
- ·
- Silver Sands
- 0.23 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $795/Night
7 Nights - US $5,565
Villa
- Jamaica
- ·
- Silver Sands
- 0.19 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $606/Night
7 Nights - US $4,239
Villa
- Jamaica
- ·
- Silver Sands
- 0.20 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
5 Baths
15 Guests
6000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $492/Night
7 Nights - US $3,443
Wheelchair Accessible Holiday Homes in Windsor
Over 19+ Wheelchair Accessible Villas and Holiday Homes in or Near Windsor
Villa
- Jamaica
- ·
- Silver Sands
- 0.03 mi to center
4.9Average
(17 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $180/Night
7 Nights - US $1,260
New
Apartment
- Jamaica
- ·
- Silver Sands
- 3.77 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
204.51 ft²
- Balcony/Terrace
- Breakfast
- Parking
- Air Conditioner
US $100/Night
7 Nights - US $700
Resort
- Montego Bay
- ·
- Falmouth
- 1.12 mi to center
9.2Exceptional
(1314 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Ocean View
US $960/Night
7 Nights - US $6,720
Villa
- Jamaica
- ·
- Silver Sands
- 0.23 mi to center
4 Bedrooms
4 Baths
10 Guests
2500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $285/Night
7 Nights - US $1,995
House
- Montego Bay
- ·
- Falmouth
- 2.45 mi to center
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1367.02 ft²
- Private Beach
- Pool
- Ocean View
- View
US $252/Night
7 Nights - US $1,764
Resort
- Jamaica
- ·
- Silver Sands
- 3.79 mi to center
8.4Excellent
(3829 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Ocean View
US $462/Night
7 Nights - US $3,231
House
- Jamaica
- ·
- Silver Sands
- 0.26 mi to center
3 Bedrooms
2 Baths
6 Guests
969 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
Child Friendly
US $182/Night
7 Nights - US $1,275
Resort
- Jamaica
- ·
- Silver Sands
- 2.38 mi to center
8.7Fabulous
(794 Reviews)
12 Baths
38 Guests
588.43 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
US $512/Night
7 Nights - US $3,584
House
- Montego Bay
- ·
- Falmouth
- 2.31 mi to center
2 Bedrooms
2 Baths
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $110/Night
7 Nights - US $770
Windsor Villas, Airbnb and Holiday Homes Under $200
Over 276+ Windsor Private Villas, Airbnb and Holiday Homes Under $200
House
- Montego Bay
- ·
- Greenwood
- 0.16 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $150/Night
7 Nights - US $1,050
Apartment
- Montego Bay
- ·
- Falmouth
- 1.79 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $85/Night
7 Nights - US $595
Apartment
- Jamaica
- ·
- Silver Sands
- 0.21 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Parking
Internet
US $162/Night
7 Nights - US $1,134
House
- Jamaica
- ·
- Silver Sands
- 0.12 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $94/Night
7 Nights - US $657
House
- Montego Bay
- ·
- Falmouth
- 0.25 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
957.99 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $105/Night
7 Nights - US $738
Apartment
- Jamaica
- ·
- Silver Sands
- 0.47 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $173/Night
7 Nights - US $1,211
Apartment
- Jamaica
- ·
- Silver Sands
- 0.19 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
2000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $136/Night
7 Nights - US $954
Apartment
- Montego Bay
- ·
- Falmouth
- 1.96 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
US $98/Night
7 Nights - US $686
House
- Montego Bay
- ·
- Falmouth
- 1.95 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $139/Night
7 Nights - US $976
Instantly Bookable Villa Rentals in Windsor
Over 231+ Instantly Bookable Private Villas in or Near Windsor
Apartment
- Jamaica
- ·
- Silver Sands
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $211/Night
7 Nights - US $1,478
House
- Jamaica
- ·
- Silver Sands
- 3.84 mi to center
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,197
House
- Montego Bay
- ·
- Falmouth
- 2.06 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Child Friendly
Security/Safety
US $169/Night
7 Nights - US $1,182
Apartment
- Jamaica
- ·
- Silver Sands
- 0.58 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $96/Night
7 Nights - US $672
Villa
- Jamaica
- ·
- Silver Sands
- 0.19 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $450/Night
7 Nights - US $3,150
Apartment
- Jamaica
- ·
- Silver Sands
- 0.83 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $232/Night
7 Nights - US $1,625
House
- Montego Bay
- ·
- Falmouth
- 2.13 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $205/Night
7 Nights - US $1,436
House
- Montego Bay
- ·
- Falmouth
- 1.98 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $161/Night
7 Nights - US $1,129
House
- Montego Bay
- ·
- Falmouth
- 2.26 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $124/Night
7 Nights - US $869
Book a Last Minute Place to Stay in Windsor
About Windsor Vacation Rentals
Discover over 455 amazing vacation rental options in Windsor 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.
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 1262.86 ft², with prices averaging US $308 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.
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Top Pickleball-Ready Accommodation Types in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 251 |
| Villas | 114 |
| Holiday Apartments | 61 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ 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 with PickleTrip™.
Frequently Asked Questions About Windsor?
What are the top vacation rentals, resorts, and hotels in Windsor 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. 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!
- Private, Ocean Front Luxury Villa - Fully Staffed, Classic Luxury Charm
- Fully Staffed, Beachside Cottage with Private Pool - 30 Sec Walk From Beach
- Beautiful VILLA SEAGULL in Silver Sands Beach Resortn3 bedroom 3.5 baths
- New Quiet Gated Ocean View Home
- 2 bedrooms 2bath home in gated area. 24 hours security.
- MODERN BEACH SIDE VILLA
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
- L&V Paradise Vacation Home with Pool and Gym
- Good Hope Coach House, historic cut stone house with modern amenities
- The Crystal at Stonebrook Manor, Falmouth, Trelawny, Jamaica
How many pickleball-ready properties have private pools in Windsor?
Discover 50 accommodations with private or nearby pickleball courts in Windsor. Some of the best destinations to stay and play pickleball are:
- Irie Smart Villa, 3-bedrooms, 3- bathrooms in Stonebrook Manor Trelawny Jamaica
- Miss P's Place Beautiful Villa with Ocean View, Pool, Mins to beach, WiFi, staff
- New 4 bedroom villa with infinity pool. 4 minute walk to Beach!
- The beautuful Butterfly Villa situated in the exclusive Silver Sands estate
Which vacation rentals, resorts, or hotels in Windsor is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Windsor? 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.
- AMAZING OCEAN & MOUNTAIN VIEWS! SLEEPS 9 THREE BEAUTIFUL BED AND BATH ROOMS
- Villa Maison de Soleil
- Vacae876
How many PickleTrip vacation rentals or resorts are available in Windsor?
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 455 properties listed in Windsor 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.
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