Beach Home Rentals in Windward, FL: Compare 10+ Sites & Save

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  4.  Florida

  5.  Port Charlotte - Charlotte Harbor
  6.  Windward

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165 Beach Home Rentals in Windward (Starting from $76)

Seaside Boca with Pool an Fire Pit
Seaside Boca with Pool an Fire Pit
House
Placida, FL, USA
1.6k from Windward center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Jacuzzis

3 Bedrooms10 Guests
New to Booking
$409
Average price / night
Check Availability
Sun, Privacy and Spacious Elegance in Cape Haze Villa!
Sun, Privacy and Spacious Elegance in Cape Haze Villa!
Villa
Placida, FL, 33946, United States
0.4k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$323
Average price / night
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Fishing, Beach, Pool Fun! Rotonda West Family Home
Fishing, Beach, Pool Fun! Rotonda West Family Home
House
Rotonda, FL, USA
1.8k from Windward center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom9 Guests
New to Booking
$302
Average price / night
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Experience the epitome of coastal luxury
Experience the epitome of coastal luxury
House
Cape Haze, FL, 33946, United States
0.5k from Windward center

AC, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
New to Booking
$295
Average price / night
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Sunny Coastal,3 BD, 2 BA, King Master Suite, Close to Ocean, Golfing , Fishing
Sunny Coastal,3 BD, 2 BA, King Master Suite, Close to Ocean, Golfing , Fishing
Villa
Rotonda West, FL, USA
2.1k from Windward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

10 reviews

$214
Average price / night
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Welcome to Links at Leeward, a relaxing coastal retreat located on the Cape Haze Links Golf Course
Welcome to Links at Leeward, a relaxing coastal retreat located on the Cape Haze Links Golf Course
House
Cape Haze, FL, 33946, United States
0.5k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Microwave, No Smoking, Toys

3 Bedrooms6 Guests
New to Booking
$154
Average price / night
Check Availability
SW Florida Luxury Modern Retreat, King Bed Suite , Close to Beaches/Golfing/Fishing/Air Ports , 2023 Built
SW Florida Luxury Modern Retreat, King Bed Suite , Close to Beaches/Golfing/Fishing/Air Ports , 2023 Built
Villa
Rotonda West, FL, USA
2.1k from Windward center

Luxury, Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
9.5

Superb

2 reviews

$196
Average price / night
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Boca Sunny Side Condo in Rotonda West ,Florida
Boca Sunny Side Condo in Rotonda West ,Florida
Condo
Rotonda West, FL, 33947, United States
0.6k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.4

Superb

6 reviews

$161
Average price / night
Check Availability
Family Villa King Bed, 3 bedrooms 2baths, 7 guests, Close to Beaches, Golfing, Fishing
Family Villa King Bed, 3 bedrooms 2baths, 7 guests, Close to Beaches, Golfing, Fishing
House
Rotonda West, FL, USA
2.2k from Windward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms7 Guests
9.7

Exceptional

4 reviews

$223
Average price / night
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Beautiful view from this Palm Island Villa with All Resort Amenities, B1313A+
Beautiful view from this Palm Island Villa with All Resort Amenities, B1313A+
Villa
Cape Haze, FL, 33946, United States
0.7k from Windward center

AC, Balcony, Barbecue, Dryer, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
8.4

Very Good

135 reviews

$514
Average price / night
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South West Florida Family Home, 3 Bedroom,2 Bathroom, King bed suite, Close to Beaches, Parks, Fishing, Golfing, Kayaking
South West Florida Family Home, 3 Bedroom,2 Bathroom, King bed suite, Close to Beaches, Parks, Fishing, Golfing, Kayaking
Villa
Rotonda West, FL, USA
2.2k from Windward center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$235
Average price / night
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Spanish Villa with Pool overlooking golf course
Spanish Villa with Pool overlooking golf course
House
Placida, FL, 33946, United States
0.7k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms9 Guests
10.0

Exceptional

7 reviews

$371
Average price / night
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Rotonda Pool Oasis Near Beaches - Sleeps 9
Rotonda Pool Oasis Near Beaches - Sleeps 9
House
Rotonda West, FL, USA
2.6k from Windward center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings

3 Bedrooms9 Guests
9.1

Superb

7 reviews

$171
Average price / night
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New Seasonal Availability- 3 Bedroom, Pool Home on Golf Course; private putting hole!
New Seasonal Availability- 3 Bedroom, Pool Home on Golf Course; private putting hole!
House
Placida, FL, 33946, United States
0.8k from Windward center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
New to Booking
$364
Average price / night
Check Availability
Duplex on CANAL all updated new furniture
Duplex on CANAL all updated new furniture
House
Rotonda West, FL, USA
2.6k from Windward center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$76
Average price / night
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Harborfront Only 26..water view from the lanai. Harborfront pool.PRIVATE BEACH
Harborfront Only 26..water view from the lanai. Harborfront pool.PRIVATE BEACH
Condo
Englewood, FL, 33946, United States
0.8k from Windward center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
8.8

Fabulous

19 reviews

$277
Average price / night
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Modern Florida Escape
Modern Florida Escape
Villa
Rotonda West, FL, USA
2.7k from Windward center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom9 Guests
New to Booking
$315
Average price / night
Check Availability
Coral Fanta Sea - Waterfront, private pool, golf, brand new construction, PARADISE
Coral Fanta Sea - Waterfront, private pool, golf, brand new construction, PARADISE
House
Placida, FL, 33946, United States
0.8k from Windward center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$252
Average price / night
Check Availability
NEW - Living The Dream - Beach,Golf,Fishing,Pool
NEW - Living The Dream - Beach,Golf,Fishing,Pool
House
Rotonda West, FL, USA
2.7k from Windward center

Laundry, Air Conditioner, Security/Safety, Balcony/Terrace, View, Guest Services, Oceanfront

4 Bedrooms10 Guests
New to Booking
$183
Average price / night
Check Availability
Beautiful Home!  Private Pool, Games, Bike to Boca Grande
Beautiful Home! Private Pool, Games, Bike to Boca Grande
House
Placida, FL, 33946, United States
0.8k from Windward center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater

5 Bedrooms10 Guests
8.8

Fabulous

23 reviews

$599
Average price / night
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Welcome to your slice of paradise.
Welcome to your slice of paradise.
Condo
Placida, FL, 33946, United States
0.9k from Windward center

AC, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$179
Average price / night
Check Availability
New coastal furniture, paint! 3 bdrm Cape Haze Resort condo; pool, pickle ball.
New coastal furniture, paint! 3 bdrm Cape Haze Resort condo; pool, pickle ball.
Condo
Placida, FL, 33946, United States
1.0k from Windward center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$224
Average price / night
Check Availability
AMAZING Cape Haze Location - picturesque setting, pool, community kayak launch
AMAZING Cape Haze Location - picturesque setting, pool, community kayak launch
House
Placida, FL, 33946, United States
1.0k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$419
Average price / night
Check Availability
Waterfront, PRIVATE beach access via free water taxi from condo property.
Waterfront, PRIVATE beach access via free water taxi from condo property.
Condo
Cape Haze, FL, 33946, United States
1.1k from Windward center

AC, Barbecue, Dryer, Elevator, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$245
Average price / night
Check Availability
Beautifully Furnished Condo Overlooking Lake!
Beautifully Furnished Condo Overlooking Lake!
Condo
Placida, FL, 33946, United States
1.1k from Windward center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

2 Bedrooms4 Guests
8.6

Fabulous

7 reviews

$164
Average price / night
Check Availability
Canal home, heated pool, close to everything!!
Canal home, heated pool, close to everything!!
House
Placida, FL, 33946, United States
1.1k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$214
Average price / night
Check Availability
AMAZING Cape Haze Location -community kayak launch
AMAZING Cape Haze Location -community kayak launch
House
Placida, FL, 33946, United States
1.2k from Windward center

AC, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$322
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Beach Rentals in Windward.

Stay Near Windward's Top Attractions

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Windward Beach Rentals on the Map

Frequently Asked Questions

You can explore 165 verified beach rentals in Windward. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Windward vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $76 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Windward offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Windward welcome pets. Currently, 28 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Windward often include amenities designed for coastal living, such as Ocean View, View, and Oceanfront. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.