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

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  2. Oceanfront Rentals
  3.  USA

  4.  Florida
  5.  Port Charlotte - Charlotte Harbor
  6.  Windward

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808 Best Oceanfront 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
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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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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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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
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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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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
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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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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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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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
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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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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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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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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
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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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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
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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
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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
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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
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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
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Little Gasparilla Home Walk to Beaches!
Little Gasparilla Home Walk to Beaches!
House
Placida, FL, USA
2.8k from Windward center

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

3 Bedrooms7 Guests
New to Booking
$298
Average price / night
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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
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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
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Perfect Florida Getaway with Private Lanai and Pool in Gated Community
Perfect Florida Getaway with Private Lanai and Pool in Gated Community
House
Placida, FL, 33946, United States
1.3k from Windward center

AC, Dryer, Free Parking, Heater, Microwave, No Smoking, Pool, TV, Washer

3 Bedrooms6 Guests
New to Booking
$184
Average price / night
Check Availability
Charming Old Florida Condo….Minutes to World Famous Beaches
Charming Old Florida Condo….Minutes to World Famous Beaches
Condo
Englewood, FL, 34224, United States
1.5k from Windward center

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

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$135
Average price / night
Check Availability
Welcome to your personal slice of paradise
Welcome to your personal slice of paradise
House
Placida, FL, 33946, United States
1.6k from Windward center

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

4 Bedrooms8 Guests
8.0

Good

3 reviews

$388
Average price / night
Check Availability
Waterfront Condo, Top Floor with Water View, THE location!  Beautiful Pool.
Waterfront Condo, Top Floor with Water View, THE location! Beautiful Pool.
Condo
Cape Haze, FL, 33946, United States
1.6k from Windward center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

4 reviews

$172
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 Oceanfront Rentals in Windward.

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Windward Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 808 verified oceanfront rentals in Windward. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Windward vary depending on the property size, exact beachfront location, and season. Rates typically start from around $76 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Windward offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Windward welcome pets. Currently, 37 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Windward often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.