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- Port Charlotte - Charlotte Harbor
- Windward
- Villa Rentals
Windward Villa Rentals & Homes
Find villas near Windward - We found 145 exact matches
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.52 mi to center
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Private Pool
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Hot Tub
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Parking
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Pool
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Private Pool
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Hot Tub
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Parking
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Pool
- Port Charlotte - Charlotte Harbor
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- Pebble Beach
- 0.27 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
- Port Charlotte - Charlotte Harbor
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- Englewood
- 7.06 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
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Pool
- Port Charlotte - Charlotte Harbor
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- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
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Pool
- Port Charlotte - Charlotte Harbor
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- White Marsh
- 0.50 mi to center
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Hot Tub
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Parking
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Pool
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Spa
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Hot Tub
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Parking
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Pool
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Spa
- Port Charlotte - Charlotte Harbor
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- Englewood
- 7.07 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
- Port Charlotte - Charlotte Harbor
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- Englewood
- 7.07 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
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- Grove City
- 0.90 mi to center
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Parking
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Spa
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Air Conditioner
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Child Friendly
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Parking
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Spa
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Air Conditioner
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Child Friendly
- Port Charlotte - Charlotte Harbor
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- Placida
- 2.11 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
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Pool
- Port Charlotte - Charlotte Harbor
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- Palm Island
- 0.50 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
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Parking
-
Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
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Parking
-
Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.48 mi to center
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Private Pool
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Parking
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Pool
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Ocean View
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Private Pool
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Parking
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Pool
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Ocean View
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.63 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.23 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
-
Pool
-
Ocean View
-
Oceanfront
-
Hot Tub
-
Pool
-
Ocean View
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.50 mi to center
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Hot Tub
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Pool
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Balcony/Terrace
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View
-
Hot Tub
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Pool
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Balcony/Terrace
-
View
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.27 mi to center
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Oceanfront
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Hot Tub
-
Pool
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Ocean View
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Oceanfront
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Hot Tub
-
Pool
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Ocean View
- Port Charlotte - Charlotte Harbor
- ·
- Cape Haze
- 0.42 mi to center
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Hot Tub
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Pool
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Balcony/Terrace
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Kitchen
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Hot Tub
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Pool
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Balcony/Terrace
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Kitchen
- Port Charlotte - Charlotte Harbor
- ·
- Pine Valley
- 0.57 mi to center
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Private Pool
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Parking
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Pool
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Ocean View
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Private Pool
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Parking
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Pool
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Ocean View
- Port Charlotte - Charlotte Harbor
- ·
- White Marsh
- 0.46 mi to center
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Private Pool
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Hot Tub
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Parking
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Pool
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Private Pool
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Hot Tub
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Parking
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Pool
- Port Charlotte - Charlotte Harbor
- ·
- Al Lago Village
- 0.10 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
- Port Charlotte - Charlotte Harbor
- ·
- Palm Island
- 0.18 mi to center
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Oceanfront
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Hot Tub
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Parking
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Pool
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Oceanfront
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Hot Tub
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Parking
-
Pool
About Windward Villa Rentals on Boca Grande Villas
Boca Grande Villas has more than 145 villas near Windward. These rentals have all the luxury accoutrements to give you comfort, including amenities such as - private swimming pools, WIFI, spas, hot tubs, and more.
Boca Grande Villas has a wide range of villa rentals near Windward, and there are different options for families, friends, or even couples. These rentals come in unique styles or sizes that would definitely suit your needs.
Boca Grande Villas offers expectational rental villas that are out of the ordinary and not found elsewhere, whether you are traveling on a beachfront, seaside, mountain, or any destination. Boca Grande Villas is an all-in-one travel platform that matches you with the perfect rental villa in Windward for your dream vacation, including top travel locations in the USA & the Rest of the World. Many have private pools, luxury bedrooms, and even features like tennis courts, beach volleyball, spas, fitness clubs & more.
Boca Grande Villas Villas are available for last-minute bookings and may include special offers for Airbnb, VRBO & Boca Grande Villas-style villas. So find your last-minute getaway today with Boca Grande Villas in Windward, and get ready to enjoy maximum comfort on your next holiday.
Frequently Asked Questions About Windward Villa Rentals
What are the top rated Villa Rentals in Windward?
There are a lot of options in Windward. If you plan on staying in the Windward area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Windward:
- Outstanding Luxury Lakeside 4 Bed Home Electric Heated Pool
- South Facing on the water, Watch the beautiful sunrises & stunning sunsets!
- Huge Pool, Gulf Coast Luxury, Peace & Quiet, Bikes
- Great Nightly Price! Gorgeous Gulf View Villa B3622A
- Spectacular Sunset Views from this Comfortable Island Villa A3124A
- 3BR Boundary Breeze Heated Pool Beach Golf Nearby
- Fabulous Fairway, heated pool, sleeps 8
- Privacy in Paradise, full refund*, heated pool, sleeps 6
- South West Florida Family Home, 3 Bedroom,2 Bathroom, King bed suite, Close to Beaches, Parks, Fishing, Golfing, Kayaking
- Tranquil 3 bed 4 bath home, fabulous heated oversized pool and spa. Welcome!
What is the rate per night for renting a villa near Windward?
At Bocagrandevillas, the average rental fee for standard villas in Windward is $369 per night. Bocagrandevillas has a large database of quality villas near Windward that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.
Do you have a villa in Windward that allows pets?
Yes, here are the top villas rentals in Windward that are pet friendly:
- Bluebell Villa. Outstanding Luxury Lakeside 4 Bedroom Villa
- Quiet Rotonda Villa, 3 Br, 2.5 Ba with recent upgrades.
- Marina One Bedroom Villa by RedAwning
- Comfortable villa with unobstructed view of the Gulf on Resort, C2424B
Are there any rental villas in Windward that are suitable for families?
Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Windward to find what works for you.
Do your rental villas in Windward have indoor swimming pools?
Based on the 2026 data from our Bocagrandevillas site, there are more than 145 private swimming pools or villas with indoor pools in or near Windward.