Windsor Holiday Rentals
- Jamaica
- Silver Sands
- 0.38 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- Montego Bay
- Falmouth
- 1.98 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 1.08 mi to center
- Hot Tub
- Spa
- Pool
- Montego Bay
- Falmouth
- 0.07 mi to center
- Pool
- Kitchen
- Parking
- Montego Bay
- Falmouth
- 2.25 mi to center
- Pool
- Balcony/Terrace
- Parking
- Montego Bay
- Falmouth
- 2.42 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Duncans
- 0.95 mi to center
- Private Pool
- Pool
- Ocean View
- Private Pool
- Oceanfront
- Pool
- Montego Bay
- Falmouth
- 1.93 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
Luxury Holiday Rentals in Windsor
- Montego Bay
- Falmouth
- 2.90 mi to center
- Private Beach
- Oceanfront
- Spa
- Jamaica
- Silver Sands
- 0.33 mi to center
- Private Pool
- Pool
- Ocean View
- Jamaica
- Silver Sands
- 0.26 mi to center
- Hot Tub
- Pool
- Balcony/Terrace
- Montego Bay
- Duncans
- 0.94 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Montego Bay
- Greenwood
- 0.17 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Jamaica
- Silver Sands
- 0.27 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Duncans
- 0.84 mi to center
- Private Pool
- Hot Tub
- Pool
- Jamaica
- Silver Sands
- 0.47 mi to center
- Oceanfront
- Pool
- Ocean View
- Jamaica
- Silver Sands
- 0.09 mi to center
- Private Pool
- Pool
- Balcony/Terrace
Top-Rated Holiday Rentals with a Pool in Windsor
- Jamaica
- Silver Sands
- 0.45 mi to center
- Private Pool
- Hot Tub
- Pool
- Jamaica
- Silver Sands
- 0.26 mi to center
- Private Pool
- Oceanfront
- Pool
- Jamaica
- Silver Sands
- 0.20 mi to center
- Private Pool
- Oceanfront
- Pool
- Jamaica
- Silver Sands
- 0.39 mi to center
- Private Pool
- Oceanfront
- Pool
- Montego Bay
- Falmouth
- 2.28 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Jamaica
- Silver Sands
- 3.56 mi to center
- Private Pool
- Oceanfront
- Pool
- Montego Bay
- Falmouth
- 1.58 mi to center
- Private Pool
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 1.60 mi to center
- Private Pool
- Pool
- Ocean View
- Jamaica
- Silver Sands
- 0.17 mi to center
- Private Pool
- Pool
- Ocean View
Pet-Friendly Holiday Rentals in Windsor
- Montego Bay
- Falmouth
- 2.26 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- Montego Bay
- Falmouth
- 2.26 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 0.25 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 2.41 mi to center
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Montego Bay
- Falmouth
- 2.30 mi to center
- Pool
- View
- Breakfast
- Montego Bay
- Falmouth
- 2.26 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- Montego Bay
- Falmouth
- 0.25 mi to center
- Oceanfront
- Pool
- Ocean View
- Pet Friendly
- Air Conditioner
- Internet
- Montego Bay
- Falmouth
- 0.25 mi to center
- Oceanfront
- Pool
- Ocean View
Large Holiday Rentals and Private Villas in Windsor
- Jamaica
- Silver Sands
- 0.19 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Oceanfront
- Fireplace/Heating
- Ocean View
- Montego Bay
- Falmouth
- 2.15 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- Montego Bay
- Duncans
- 0.85 mi to center
- Private Pool
- Hot Tub
- Pool
- Montego Bay
- Florence Hall Village
- 0.08 mi to center
- Oceanfront
- Pool
- Ocean View
- Jamaica
- Silver Sands
- 0.23 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Montego Bay
- Falmouth
- 0.08 mi to center
- Private Pool
- Oceanfront
- Pool
- Jamaica
- Silver Sands
- 0.19 mi to center
- Private Pool
- Oceanfront
- Pool
- Jamaica
- Silver Sands
- 0.20 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
Wheelchair Accessible Holiday Homes in Windsor
- Jamaica
- Silver Sands
- 0.03 mi to center
- Ocean View
- Balcony/Terrace
- View
- Montego Bay
- Falmouth
- 2.45 mi to center
- Private Beach
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 1.12 mi to center
- Hot Tub
- Spa
- Pool
- Jamaica
- Silver Sands
- 0.23 mi to center
- Private Pool
- Pool
- Balcony/Terrace
- Jamaica
- Silver Sands
- 2.38 mi to center
- Private Beach
- Oceanfront
- Hot Tub
- Jamaica
- Silver Sands
- 3.79 mi to center
- Hot Tub
- Spa
- Pool
- Jamaica
- Silver Sands
- 0.26 mi to center
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Jamaica
- Silver Sands
- 2.70 mi to center
- Private Beach
- Oceanfront
- Hot Tub
- Montego Bay
- Falmouth
- 2.31 mi to center
- Pool
- Balcony/Terrace
- Kitchen
Windsor Private Villas and Holiday Homes Under $200
- Montego Bay
- Greenwood
- 0.16 mi to center
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Montego Bay
- Falmouth
- 1.79 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Jamaica
- Silver Sands
- 0.21 mi to center
- Balcony/Terrace
- Kitchen
- Parking
- Montego Bay
- Falmouth
- 2.13 mi to center
- Kitchen
- Parking
- Air Conditioner
- Montego Bay
- Falmouth
- 0.25 mi to center
- Fireplace/Heating
- Balcony/Terrace
- View
- Jamaica
- Silver Sands
- 0.19 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- Montego Bay
- Falmouth
- 1.68 mi to center
- Hot Tub
- Ocean View
- Balcony/Terrace
- Jamaica
- Silver Sands
- 0.12 mi to center
- Ocean View
- Balcony/Terrace
- View
- Montego Bay
- Falmouth
- 2.02 mi to center
- Balcony/Terrace
- Kitchen
- Parking
Instantly Bookable Holiday Homes in Windsor
- Jamaica
- Silver Sands
- 0.47 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- Jamaica
- Silver Sands
- 3.84 mi to center
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Montego Bay
- Falmouth
- 2.53 mi to center
- Child Friendly
- Security/Safety
- Montego Bay
- Falmouth
- 0.36 mi to center
- Pool
- Kitchen
- Parking
- Jamaica
- Silver Sands
- 0.58 mi to center
- Ocean View
- Balcony/Terrace
- View
- Montego Bay
- Falmouth
- 1.89 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Jamaica
- Silver Sands
- 0.83 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 1.98 mi to center
- Oceanfront
- Pool
- Ocean View
- Montego Bay
- Falmouth
- 0.22 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
Book a Last Minute Place to Stay in Windsor
About Casai's Private Villas and Holiday Rentals in Windsor
Discover more than 456 vacation rentals available in Windsor. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windsor.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windsor, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windsor. On average, places to stay near Windsor offer 1354.39 ft², with nightly prices averaging US $310.
With Casai, finding and comparing holiday rentals in Windsor is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 252 |
| Villas | 112 |
| Holiday Apartments | 63 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in Windsor
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windsor.
Frequently Asked Questions About Windsor?
What are the top holiday rentals in Windsor?
With numerous options available in Windsor, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windsor:
- 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
- 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
- Simmerdown Villa is a spacious modern 4 bedroom house within a gated community
- Silversands Trelawny, SUNSET 1 - Your Villa by the sea
- 3 Bedroom villa with pool on private gated community
How many holiday rentals have private pools in Windsor?
Discover a selection of holiday rentals with private pools near Windsor with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- 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 holiday homes in Windsor are best for families?
If you're searching for a family-friendly holiday home in Windsor, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windsor:
- AMAZING OCEAN & MOUNTAIN VIEWS! SLEEPS 9 THREE BEAUTIFUL BED AND BATH ROOMS
- Villa Maison de Soleil
- Vacae876
How many Casai.com holiday rentals are available in Windsor?
As of 2026, Casai boasts over 456 properties listed in the Windsor area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windsor.







































































