Stay well, then step out and discover Windward.
Best Stays by Sonder
Windward
Find places to stay in Windward. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
Popular stays in Windward
Start where you want to be in Windward. Then compare space, amenities and style.
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Close to everything worth your time.
Stay genuinely central in Windward when you want dinner, sights, and the best neighborhoods within an easy walk, without sorting through places too far from the reason you came.
Sonder hasn't arrived in Windward yet. You may like these stays from trusted partners
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Oceanfront
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Pool
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Ocean View
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View
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Oceanfront
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Parking
-
Pool
-
Ocean View
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
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Parking
-
Pool
-
Balcony/Terrace
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Kitchen
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Pool
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Ocean View
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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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Kitchen
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Air Conditioner
Windward answers before you book.
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 Vacation Rentals in Windward:
- Beautiful Beaches at LGI Hideaway Golf Cart
- Palm Island Beachfront ! Live on the beach!
- Bird's Nest has a birds eye view! PRIVATE ISLAND
- Intracoastal Waterfront Luxury Condo
- SeaSalt: Oceanview condo with pool!
- 8 Mi to Beach w/Pool Access: Englewood Condo!
- Waterfront Retreat in Rotonda West golf community
- TwoMorrows Treasure: Beaches,Pickleball on Property,Boating,Biking, Golf, Nature
- 2 Bedrooms on the beach!
- Pool Access! Private Island Condo in Placida
There are 451 vacation rentals with private pools near Windward. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Windward, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward:
Currently, the total number of properties listed in 2026 is over 21 in the Windward area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward.