Wyknot Cabin - Vacation Rentals in Windward

Little Gasparilla Island: WATERFRONT Cabin, Boat dock at front door! in Placida From US $338
         

10.0 (69 Reviews)
Cabin
Little Gasparilla Island: WATERFRONT Cabin, Boat dock at front door!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury Places to Stay in Windward

Over 1228+ Luxury Places to Stay in or Near Windward
Cozy 3 bedroom 2 bathroom house. in Rotonda West From US $6,509
         

New
House
Cozy 3 bedroom 2 bathroom house.
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Experience luxury at The Lookout, a 3-bedroom home in scenic Placida, FL with ocean views. in Placida From US $2,800
         

New
House
Experience luxury at The Lookout, a 3-bedroom home in scenic Placida, FL with ocean views.
  • Air Conditioner
  • Pool
  • TV

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`Dreamy Beachfront Getaway !` in Placida From US $2,013
         

New
House
`Dreamy Beachfront Getaway !`
  • Air Conditioner
  • Parking
  • TV

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Relax under the Tiki Hut. Build memories! Without the Boca Grande price tag! in Englewood From US $1,619
         

10.0 (17 Reviews)
House
Relax under the Tiki Hut. Build memories! Without the Boca Grande price tag!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beach House in Placida From US $1,440
         

New
House
Beach House
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  • Parking
  • Pet Friendly

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Anglers Club- Waterfront 3-bedroom townhome in Placida, FL that sleeps up to 6 guests. in Placida From US $1,331
         

10.0 (1 Review)
House
Anglers Club- Waterfront 3-bedroom townhome in Placida, FL that sleeps up to 6 guests.
  • Air Conditioner
  • Pet Friendly
  • Pool

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Anglers Club ~ beautiful 4/3 townhome in Placida From US $1,229
         

9.8 (7 Reviews)
House
Anglers Club ~ beautiful 4/3 townhome
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunset Beach Cottage North in Englewood From US $1,174
         

10.0 (6 Reviews)
Cottage
Sunset Beach Cottage North
  • Air Conditioner
  • Parking
  • Pet Friendly

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Top-Rated Vacation Rentals with a Pool in Windward

Over 802+ Top-Rated Vacation Rentals with a Pool in or Near Windward
Waterfront 2BR beach & lagoon retreat. Dock, pool, dog-friendly, tennis in Placida From US $410
         

10.0 (105 Reviews)
Condo
Waterfront 2BR beach & lagoon retreat. Dock, pool, dog-friendly, tennis
  • Air Conditioner
  • Parking
  • Pet Friendly

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A Little Slice of Paradise in Cape Haze From US $222
         

10.0 (100 Reviews)
Condo
A Little Slice of Paradise
  • Air Conditioner
  • Parking
  • Pool

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Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West in Rotonda West From US $229
         

10.0 (93 Reviews)
Villa
Modern Luxury Villa/Riverfront/Heated South Facing Pool/Golf Rotonda West
  • Air Conditioner
  • Parking
  • Pool

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3 bed/3 bath with Stunning Lakeview from private pool in Rotonda West From US $268
         

10.0 (91 Reviews)
House
3 bed/3 bath with Stunning Lakeview from private pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa. in Rotonda West From US $306
         

10.0 (84 Reviews)
House
Light and airy, beautifully appointed 3 bed, 3 bath home with sunny pool & spa.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo! in Placida From US $319
         

10.0 (77 Reviews)
Condo
Seeing is Believing! Incredible Boca Vista Harbor Waterfront Condo!
  • Air Conditioner
  • Parking
  • Pool

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Island Breeze in Rotonda West From US $331
         

10.0 (74 Reviews)
House
Island Breeze
  • Air Conditioner
  • Parking
  • Pool

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The Caddyshack in Rotonda West From US $227
         

10.0 (72 Reviews)
House
The Caddyshack
  • Air Conditioner
  • Pool
  • TV

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Pet-Friendly Vacation Rentals in Windward

Over 434+ Pet-Friendly Vacation Rentals in or Near Windward
Quiet Rotonda Villa, 3 Br, 2.5 Ba with recent upgrades. in Rotonda West From US $186
         

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10.0 (5 Reviews)
Villa
Quiet Rotonda Villa, 3 Br, 2.5 Ba with recent upgrades.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfortable villa with unobstructed view of the Gulf on Resort, C2424B in Cape Haze From US $468
         

9.2 (114 Reviews)
Villa
Comfortable villa with unobstructed view of the Gulf on Resort, C2424B
  • Air Conditioner
  • Parking
  • Pet Friendly

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Heated Pool: Canal-front Rotonda West Retreat in Rotonda West From US $298
         

|
10.0 (2 Reviews)
Cottage
Heated Pool: Canal-front Rotonda West Retreat
  • Air Conditioner
  • Pet Friendly
  • Pool

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*Pet Friendly - Direct GULF Front - Palm Island * in Placida From US $590
         

8.8 (34 Reviews)
House
*Pet Friendly - Direct GULF Front - Palm Island *
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tropical Retreat, full refund*, heated pool, dog ok in Rotonda West From US $238
         

9.8 (11 Reviews)
Villa
Tropical Retreat, full refund*, heated pool, dog ok
  • Air Conditioner
  • Parking
  • Pet Friendly

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Gulf Coast Paradise w/Heated Pool -12 min drive to Ocean Beach-Relaxing 3-2-2. in Rotunda West From US $175
         

9.8 (30 Reviews)
House
Gulf Coast Paradise w/Heated Pool -12 min drive to Ocean Beach-Relaxing 3-2-2.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Suntan | Canal view | Pool | Bikes in Rotonda West From US $272
         

New
House
Suntan | Canal view | Pool | Bikes
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Oasis: Rotonda West Canal #202 in Rotonda West From US $179
         

8.4 (5 Reviews)
House
Waterfront Oasis: Rotonda West Canal #202
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Windward

Over 233+ Large Vacation Homes & Villas in or Near Windward
Superb Home Perfect Place in Rotonda West From US $151
         

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8.6 (5 Reviews)
Villa
Superb Home Perfect Place
  • Air Conditioner
  • Parking
  • Pet Friendly

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Bluebell Villa. Outstanding Luxury Lakeside 4 Bedroom Villa in Rotonda West From US $312
         

9.6 (53 Reviews)
Villa
Bluebell Villa. Outstanding Luxury Lakeside 4 Bedroom Villa
  • Air Conditioner
  • Parking
  • Pool

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Marina One Bedroom Villa by RedAwning in Englewood From US $194
         

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6.0 (1 Review)
Villa
Marina One Bedroom Villa by RedAwning
  • Air Conditioner
  • Parking
  • Pool

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Dolphin Watch | Beachfront on private Beach in Cape Haze From US $1,142
         

9.8 (13 Reviews)
House
Dolphin Watch | Beachfront on private Beach
  • Air Conditioner
  • Parking
  • TV

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Waterfront Paradise On a Private Peninsula with Resort Amenities A1221H in Cape Haze From US $240
         

8.4 (139 Reviews)
Villa
Waterfront Paradise On a Private Peninsula with Resort Amenities A1221H
  • Air Conditioner
  • Parking
  • Pool

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The Sunsets are amazing from this newly renovated villa on the Gulf, B1211A+ in Cape Haze From US $438
         

9.2 (122 Reviews)
Villa
The Sunsets are amazing from this newly renovated villa on the Gulf, B1211A+
  • Air Conditioner
  • Parking
  • Pool

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Amazing! Gulfview Villa in Beautiful Quiet Resort C0036A in Cape Haze From US $573
         

9.2 (58 Reviews)
Villa
Amazing! Gulfview Villa in Beautiful Quiet Resort C0036A
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  • Pool

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Enjoy a Beautiful Gulf Sunset from the Screened Porch on Resort Villa A3221B in Cape Haze From US $267
         

9.6 (88 Reviews)
Villa
Enjoy a Beautiful Gulf Sunset from the Screened Porch on Resort Villa A3221B
  • Air Conditioner
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  • Pool

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Wheelchair Accessible Vacation Homes in Windward

Over 83+ Wheelchair Accessible Vacation Homes in or Near Windward
The Ultimate 2 Bedroom Condo on Charlotte Harbor, Orlando Condo 1005 in Englewood From US $345
         

New
Villa
The Ultimate 2 Bedroom Condo on Charlotte Harbor, Orlando Condo 1005
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

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Boca Vista - Stunning water views, kayaks in Placida From US $317
         

10.0 (23 Reviews)
Condo
Boca Vista - Stunning water views, kayaks
  • Air Conditioner
  • Parking
  • Pool

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Palm Island Beachfront ! Live on the beach! in Placida From US $512
         

10.0 (15 Reviews)
Condo
Palm Island Beachfront ! Live on the beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beauty, comfort and peace! in Placida From US $209
         

10.0 (6 Reviews)
House
Beauty, comfort and peace!
  • Air Conditioner
  • Parking
  • Pool

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A LUXURY RESORT STYLE CONDO - THE POSSIBILITIES ARE AS ENDLESS AS THE SUNSHINE in Placida From US $425
         

10.0 (4 Reviews)
Condo
A LUXURY RESORT STYLE CONDO - THE POSSIBILITIES ARE AS ENDLESS AS THE SUNSHINE
  • Air Conditioner
  • Parking
  • Pool

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Ideal Tarpon Fishing condo with dock slip in Placida Florida! in Placida From US $362
         

10.0 (4 Reviews)
Condo
Ideal Tarpon Fishing condo with dock slip in Placida Florida!
  • Air Conditioner
  • Parking
  • Pool

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NEW! Palm Island with private pool, garage, screened porches, dock, 2 kayaks in Englewood From US $607
         

10.0 (2 Reviews)
House
NEW! Palm Island with private pool, garage, screened porches, dock, 2 kayaks
  • Air Conditioner
  • Parking
  • Pool

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Modern gated renovated 3BR townhome near beaches & Boca G with resort amenities! in Placida From US $241
         

10.0 (2 Reviews)
House
Modern gated renovated 3BR townhome near beaches & Boca G with resort amenities!
  • Air Conditioner
  • Parking
  • Pool

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Windward Vacation Rentals and Airbnb Places to Stay Under $200

Over 170+ Windward Vacation Rentals and Airbnb Places to Stay Under $200
Bay Watch on Little Gasparilla Island, accessible by water taxi and boat only in Placida From US $192
         

10.0 (2 Reviews)
House
Bay Watch on Little Gasparilla Island, accessible by water taxi and boat only
  • Air Conditioner
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  • Pet Friendly

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Vacation Paradise 2bd 2bath Unit A in Rotonda West From US $165
         

10.0 (20 Reviews)
House
Vacation Paradise 2bd 2bath Unit A
  • Air Conditioner
  • Parking
  • TV

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Golf, Freshwater Pond, Pool & Huttub - The Happy Bunker- Roelens Vacations in Rotonda West From US $167
         

8.0 (3 Reviews)
House
Golf, Freshwater Pond, Pool & Huttub - The Happy Bunker- Roelens Vacations
  • Air Conditioner
  • Pool
  • Private Pool

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Family friendly Golfers dream in Rotonda West in Rotonda West From US $157
         

10.0 (3 Reviews)
House
Family friendly Golfers dream in Rotonda West
  • Air Conditioner
  • Parking
  • TV

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Beautiful Boca Grande Townhouse in Placida From US $196
         

10.0 (1 Review)
House
Beautiful Boca Grande Townhouse
  • Air Conditioner
  • Parking
  • Pool

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8 Mi to Beach w/Pool Access: Englewood Condo! in Englewood From US $167
         

10.0 (1 Review)
Condo
8 Mi to Beach w/Pool Access: Englewood Condo!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beautiful Rotonda Condo 2 Bed 2 Bath Pool Walkable Near Beaches Monthly Rental in Rotonda West From US $120
         

10.0 (1 Review)
Condo
Beautiful Rotonda Condo 2 Bed 2 Bath Pool Walkable Near Beaches Monthly Rental
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Retreat in Rotonda West golf community in Rotonda West From US $119
         

10.0 (1 Review)
Condo
Waterfront Retreat in Rotonda West golf community
  • Air Conditioner
  • Parking
  • Pet Friendly

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Instantly Bookable Vacation Homes in Windward

Over 702+ Instantly Bookable Vacation Homes in or Near Windward
HAPPY HIDEAWAY - Closest Gulf-Front Unit to the Beach – No Resort fees. Sleeps 6 in Placida From US $351
         

9.8 (73 Reviews)
Condo
HAPPY HIDEAWAY - Closest Gulf-Front Unit to the Beach – No Resort fees. Sleeps 6
  • Air Conditioner
  • Parking
  • Pool

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Salty Mermaid on Little Gasparilla Island! Come get salty! in Placida From US $420
         

10.0 (13 Reviews)
House
Salty Mermaid on Little Gasparilla Island! Come get salty!
  • Air Conditioner
  • TV
  • View

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ISLAND LIVING! Ferry, parking is free! Closest bldg to beach. in Placida From US $375
         

10.0 (42 Reviews)
Condo
ISLAND LIVING! Ferry, parking is free! Closest bldg to beach.
  • Air Conditioner
  • Parking
  • Pool

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Paradise on LGI! Golf Cart, Pool & Private Beach, Free parking & Free ferry in Placida From US $242
         

9.6 (42 Reviews)
Condo
Paradise on LGI! Golf Cart, Pool & Private Beach, Free parking & Free ferry
  • Air Conditioner
  • Parking
  • Pool

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Little Gasparilla Island - Gulf view, golf cart, ferry, pool, boat dock, parking in Placida From US $347
         

9.8 (97 Reviews)
Condo
Little Gasparilla Island - Gulf view, golf cart, ferry, pool, boat dock, parking
  • Air Conditioner
  • Parking
  • Pool

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Waterfront Sleeps 8 on the bay Beach-to-Bay private land; Dock-Wildlife-Secluded in Placida From US $680
         

10.0 (21 Reviews)
House
Waterfront Sleeps 8 on the bay Beach-to-Bay private land; Dock-Wildlife-Secluded
  • Air Conditioner
  • Parking
  • TV

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Sea La Vie - Direct Gulf Front - Amazing Sunsets - Private Island in Placida From US $641
         

8.4 (22 Reviews)
House
Sea La Vie - Direct Gulf Front - Amazing Sunsets - Private Island
  • Air Conditioner
  • TV
  • View

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Rotonda River Villa pool home #1125 in Rotonda West From US $264
         

9.8 (19 Reviews)
House
Rotonda River Villa pool home #1125
  • Air Conditioner
  • Pool
  • TV

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About Windward Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Wyknotcabin Windward, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windward. Places to stay near Windward are 900 ft² on average, with prices averaging US $338 a night.

Wyknotcabin makes it easy and safe to find and compare vacation rentals in Windward with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windward

Type Count
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windward

★ Pro Tip: Wyknotcabin makes it easy to compare the best listings on Wyknotcabin homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wyknotcabin homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windward.

Weather in Windward

View the weather forecast for Windward before booking your Windward Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Windward Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Windward?

Currently, the total number of properties listed in 2026 is over 1 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.