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Tailwind South: Beautiful 3 bedroom across the street from Beach!

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Exterior - Tailwind South: Beautiful 3 bedroom across the street from Beach! (Placida)
Beach nearby - Tailwind South: Beautiful 3 bedroom across the street from Beach! (Placida)
Outdoor dining - Tailwind South: Beautiful 3 bedroom across the street from Beach! (Placida)
TV - Tailwind South: Beautiful 3 bedroom across the street from Beach! (Placida)
TV - Tailwind South: Beautiful 3 bedroom across the street from Beach! (Placida)
Escape to this 3 bedroom, 2 bath haven on Bocilla Bay with direct access to the beach and gulf views. Enjoy a private boat dock, open sun deck and screened lanai overlooking the water. This pet-friendly home is located in an association featuring a heated swimming pool, lighted tennis court and more.

Reviews

9.0 out of 10
Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 8212 sq m

Popular amenities

  • Ocean view
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Air-conditioning

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About this property

Tailwind South: Beautiful 3 bedroom across the street from Beach!

  • "UPDATE from Hurricanes Helene and Milton
    As of January 2026,
    Tennis courts are ready to go!
    Docks have been rebuilt and ready to go!
    POOL: NOT AVAILABLE for the 2026 season. Information for 2027 should be available before summer of 2026"

    Seasonal-Pristine 3 bedroom, 2 bath home with gulf views and a private boat dock. This home is located directly across the street from the beach on Bocilla Bay. Bathtub in master bath is even raised to view the water with limestone and sea glass tile accents. Living room has a pull out queen sofa bed and 2 pull out trundle beds! Hardwood flooring throughout, completely updated kitchen and baths, private boat dock, outside shower, open sun deck and screened lanai overlooking water. .This home is pet friendly with prior approval. We will accept ONE small to medium dog only. Have you vacationed on the island before? Palm Island a.k.a. Don Pedro Island, is a barrier island 7 miles long between Sarasota and Ft. Myers on the Gulf coast with sugar-sand beaches, beautiful harbors and lagoons, great fishing and shelling only accessible by a short 10 minute car ferry or private boat. Our beaches are some of the most pristine and quiet in all of coastal Florida. There are no high rises blocking your Gulf views, unpaved sandy roads, and a relaxed "Old Florida" atmosphere. There is one restaurant called the Rum Bay that serves lunch and dinner. The car ferry runs continually from 6:30 am until 10:00 pm from Sunday through Thursday and until 11:00 pm Friday and 12:00 midnight Saturday. You drive your car onto the ferry and then directly to your vacation rental home. It's a very special place to vacation. We have kayak rentals and golf cart rentals for your use during your vacation. All of our properties on Palm Island require a ferry ride to get there. One round trip on the ferry for car and passengers costs $55. The alternative is to purchase a book of 10 round trips for $400, or $40 per round trip. For more information on the ferry, google Palm Island Transit.

    Pet Policy: This home is Pet Friendly home. This means that ONE dog is permitted to stay at the rental. No cats are permitted in any of our properties. Certain aggressive breeds as designated by the State of Florida and outlined in our rental contract are not permitted. No exceptions will be made to this policy.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Communal pool

Internet

  • Available in the house: Internet access

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Cobblestone flooring in public areas
  • Smoke-free property

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Unit size: 2,280 square feet

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Exterior
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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the area

Located near the beach, this holiday home is in Palm Island, a neighbourhood in Placida. Oyster Creek Golf Club and Gasparilla Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Venice Beach and Englewood Beach. Visit our Placida travel guide
View more Holiday homes in Placida
Map
Placida, FL

What's nearby

  • Stump Pass Beach State Park
    Stump Pass Beach State Park
    9 min drive - 5.8 km
  • Don Pedro Island Beach
    2 min walk - 0.2 km
  • Don Pedro Island State Park
    17 min walk - 1.5 km
  • Lemon Bay
    6 min drive - 4.1 km

Getting around

  • Punta Gorda Airport (PGD)
    47 min drive

Restaurants

  • Starbucks
  • Steamers Oyster Bar
  • Circle K
  • Cool Pickle In Paradise
  • The Lighthouse Grill

Frequently asked questions

Is Tailwind South: Beautiful 3 bedroom across the street from Beach! pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Tailwind South: Beautiful 3 bedroom across the street from Beach!?

On-site parking is available at the property.

What time is check-in at Tailwind South: Beautiful 3 bedroom across the street from Beach!?

Check-in begins at 4:00 PM.

What time is check-out at Tailwind South: Beautiful 3 bedroom across the street from Beach!?

Checkout is at 10:00 AM.

Where is Tailwind South: Beautiful 3 bedroom across the street from Beach! located?

Located in Palm Island, this holiday home is within a 15-minute walk of Don Pedro Island Beach and Don Pedro Island State Park. Lemon Bay and Little Gasparilla Island Beach are also within 3 miles (5 km).

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Tailwind South: Beautiful 3 bedroom across the street from Beach! Reviews

Reviews

Wonderful

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 5 out of 8 reviews
Rating 8 - Good. 2 out of 8 reviews
Rating 6 - Okay. 1 out of 8 reviews
Rating 4 - Poor. 0 out of 8 reviews
Rating 2 - Terrible. 0 out of 8 reviews

8.8

Cleanliness

9.0

Location

Reviews

Verified

8/10 Good

Jack B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Vacation stay

We had a great time and the house was well equipped with any cooking equipment you would need, making dinner for the family easy. The views were gorgeous and the pool being in close proximity was very nice as well. The AC stayed cold and was nicely decorated and modern. I would stay here again!
Stayed 10 nights in Jun 2023
Verified

10/10 Excellent

Laura B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring break 2024

Great place for a relaxing week on the beach, we would love to go back.
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

James H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A great beach stay

We stayed for three nights at the Captains Quarters and all four of us agreed we would like to return. A lovely, roomy, nicely furnished home well set up for a family stay. Lots of places for people to find a quiet spot to sit and read. Great decks and a screened porch. Not enough hot water for everyone’s shower though.
Stayed 3 nights in Jan 2020
Verified

10/10 Excellent

Laurie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer 2021

The house had plenty of space for all. It was comfortable with a super floor plan. The kitchen was set up nicely, the family room and large table made for fun evenings over dinner, games, and desserts. A quick walk across the street was perfect for the gorgeous sunsets.
Stayed 7 nights in Aug 2021
Verified

8/10 Good

Matt S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute place

Nice cozy and tropical feel
Stayed 7 nights in May 2021
Verified

6/10 Okay

John D.

Liked: Check-in, communication
Disliked: Location

Be prepared

The area is like being stranded on an island. There is NO stores, one restaurant with very limited hours. The ferry is a barge fee was never disclosed for each car each trip. These things are not explained in the listing. Then the say you can only access the one restaurant by golf cart. Another unexpected fee. Very expensive. This is misleading because you can take a free golf cart ride to the restaurant from the parking lot. Also not explained. $$$$ of extra expenses
Stayed 7 nights in Mar 2021
Verified

10/10 Excellent

Mindel D.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Wonderful house on Palm Island

Great place to stay on Palm Island. Beautiful house -- great for many people, with lots of outside areas to hang out. Fabulous views from the very top of the house to the deck views.
Stayed 7 nights in Dec 2020
Verified

10/10 Excellent

Susie H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Captains Quarters

The location is amazing. Great layout in the house. Could have been cleaner on arrival. Property manager worked hard to make things right. Overall, an excellent stay.
Stayed 7 nights in Aug 2020