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Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts

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 Welcom to Gypsy Wind
 Whether you're returning from a day of adventure or stepping inside for the first time, the entrance to Gypsy Wind invites you to leave your worries behind and embrace the comfort and beauty of this coastal haven.
The home features an inviting open-concept floor plan that seamlessly connects the living, dining, and kitchen areas.
The chef's kitchen is a culinary masterpiece, anchored by a professional-grade 6-burner gas stove with precise temperature controls- perfect for preparing everything from multi-course meals to quick dinners.
The open kitchen with bar seating seamlessly blends style and functionality, creating a welcoming space for cooking, dining, and socializing.

Reviews

10 out of 10
Exceptional
5 bedrooms4+ bathroomsSleeps 123000 sq ft

Popular amenities

  • Dryer
  • Hot tub
  • Washer
  • Pool
  • Air conditioning
  • Barbecue grill

Explore the area

Map
Captiva, Florida
  • North Captiva Island Beach
    ‪1 min walk‬
  • Cayo Costa Beaches
  • Useppa Island
  • Fort Myers, FL (RSW-Southwest Florida Intl.)

Rooms & beds

5 bedrooms (sleeps 12)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

3 Single Beds

Living Room 1

1 Double Sofa Bed

4 bathrooms, 1 half bathroom

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Garden
Dining area

About this property

Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts

Summary:
🌊 Gulf Front Paradise
🏊‍♂️ Heated Private Saltwater Pool
🌅 Hot Tub Bliss: Enjoy stunning sunsets from the second-level hot tub
🏠 Room for All: 3 king suites, 1 queen, a bunk room, & pull-out couch
🍳 Gourmet Kitchen: Featuring Sub-Zero & Viking appliances.
🎉 Packed with Fun: Beach gear, pool toys, bikes, golf carts, kayaks, paddleboards & more!
🚤 Dock Available for your private vessel
🤝 24/7 Superhost Support: Personalized care from booking to checkout.

The Space:
Nestled directly on the Gulf of Mexico, Gypsy Wind is a stunning beachfront estate offering turquoise water views from nearly every room. This three-story retreat blends luxury, comfort, and adventure to create the ultimate vacation experience for guests of all ages.
Start your mornings with coffee on the expansive wraparound screened-in porches, or relax with a book in the bright, airy living room, where fully stacking sliding glass doors seamlessly merge indoor and outdoor living.

After hours at the beach, enjoy lunch at the outdoor kitchen and bar while the kids splash and play in the pool. Adventure awaits with kayaks, paddleboards, golf carts, and bikes, perfect for exploring the island and its scenic preserves.

As the sun sets, unwind in the hot tub with a drink in hand while the sunset transforms the sky into a work of art. Later, prepare a gourmet meal in the chef’s kitchen, equipped with top-of-the-line appliances and all the essentials for memorable dining experiences.
Gypsy Wind isn’t just a home—it’s a destination for creating unforgettable memories.

Explore Gypsy Wind’s Thoughtfully Designed Spaces
🌅 Top Floor:
The top floor features an open-concept living area with a chef’s kitchen equipped with Sub-Zero and Viking appliances, a spacious dining room, and a cozy living room. Fully stacking sliding glass doors lead to an oversized screened-in porch with dining and lounge seating, offering unobstructed Gulf views—perfect for meals or relaxing under the stars.

🛏️ Second Floor:
This level includes three king suites, each with private access to a wraparound screened-in porch with stunning Gulf views. Enjoy the cozy swing bed, a bedroom-level coffee station, and a hot tub, ideal for unwinding after a day of adventure.

🏖️ Ground Floor:
The ground floor is designed for families, featuring a queen bedroom, a kids’ bunk room, and a shared bathroom. Step outside to the seaside pool deck, complete with a heated saltwater pool, an outdoor kitchen, a bar, and a large television—perfect for poolside relaxation or entertaining.

Entertainment
🌊 Fully equipped beachfront setup with chairs, umbrellas, cooler, and more.
🏊‍♂️ Heated saltwater pool and deck-level hot tub both overlooking the gulf!.
🍹 Outdoor kitchen and Tiki bar with a large TV.
🚿 Convenient outdoor hot/cold shower.
🛶 Kayaks and paddleboards for water adventures.
🚴 Beach cruiser bikes to explore the island.
🚤 Dock space available for your boat (ask about availability and cost).
🎉 Outdoor games and a beachfront hammock for relaxation and fun.
🔥 Two propane BBQ grills—one near the kitchen and one by the pool.
🎾 Safety Harbor Club membership, with access to tennis courts, pickleball courts, and an additional pool.

Convenience
🚗 Two golf carts: a six-seater and a four-seater for exploring the island.
🛗 Three-story elevator for effortless accessibility.
🧺 Two laundry rooms, both with full-size washers and dryers.
🧊 Two oversized refrigerators provide plenty of space for groceries for the whole group.
🌐 High-speed Starlink internet for staying connected.
💧 Full-house reverse osmosis water system for clean, fresh water.

Main Living Area: The spacious, open-concept main living area includes:
🍳 A chef’s kitchen fully equipped with Sub-Zero and Viking appliances.
🌬️ New stacking sliding doors for a seamless indoor-outdoor experience.
🍽️ Three dining areas: one inside,onth eporch, and the third on the pool deck.
🛋️ A living room with an oversized, comfortable pull-out couch perfect for family movie nights.

Bedrooms and Bathrooms
1. Palm Suite: Second-level king suite with a walk-in closet, en suite bathroom, dual-head shower, and whirlpool tub overlooking the Gulf. Direct porch access with seating and hot tub.
2. Reef Suite: Second-level king suite with a four-poster bed, two spacious closets, en suite bathroom, and access to the wraparound porch with a swing bed and coffee station.
3. Flamingo Suite: Second-level king suite with an en suite bathroom and serene views of the palm grove from the wraparound porch.
4. Tarpon Lodge: Ground-floor queen bedroom with easy access to the pool and beach, located next to the kids’ bunk room.
5. Dolphin Cove: Kids’ bunk room with three bunk beds and an HD Bluetooth projector with a large screen—perfect for winding down after a day of fun.

Bathrooms:
- Three en suite bathrooms in the king suites.
- A fourth full bathroom on the top floor, adjacent to the kitchen.
- A half bath on the ground floor.
- An outdoor hot/cold shower by the pool.
Each bathroom is stocked with plush towels and luxury toiletries, including shampoo, conditioner, body wash, and more.

Why Choose Gypsy Wind?
1. Prime Location: Direct beachfront access with unobstructed Gulf views.
2. Luxurious Design: A 5-bedroom, 4.5-bathroom masterpiece blending elegance and island charm.
3. Unmatched Amenities: Heated saltwater pool, hot tub, Tiki bar, and endless activities for everyone.

About North Captiva Island:
Nestled off the coast of southwest Florida, North Captiva Island, a boat access only private island locally known as a hidden gem, offers a tranquil escape from the bustling world. With its pristine beaches, crystal-clear turquoise waters, and lush tropical landscapes, North Captiva Island is a paradise for nature lovers and those seeking a peaceful retreat. Explore miles of pristine shoreline, witness stunning sunsets over the gulf, and immerse yourself in the island's laid-back atmosphere. Whether you're strolling along the sandy beaches, engaging in water activities, or simply unwinding in the embrace of nature, North Captiva Island promises an idyllic and unforgettable experience!!
Don’t just visit the beach—immerse yourself in the luxury of Gypsy Wind. Book your stay today and create memories that will last forever!

Guest Access:
We’ll warmly welcome you at the dock, provide golf carts for your convenience, and guide you to your island home. Guests enjoy exclusive access to the entire home and property, providing complete privacy and comfort throughout your stay.

The Neighborhood:
North Captiva Island is a private island that has just over 350 houses. The island is extremely special with miles of beautiful beaches, world-class shelling, birding, fishing, and of course true relaxation.

The whole island is only four miles long (and ½ mile wide at the widest part), but about half of the island is owned by the State of Florida and managed as a preserve that offers residents and guests miles of hiking trails and access to extremely remote and private white sand beaches.
The island has three restaurants (two serving casual fare and other more gourmet meals), an Island Market (not a grocery store, but has as few last-minute items), ice cream shop/boutique and an island store. There are several wonderful private chef options too!

Our island features golf carts on sandy roads only. This island is a very special and unique place, unlike any other vacation or have or will ever take… it is perfect for creating amazing memories that will last a lifetime.

Getting Around:
Enjoy the convenience of two golf carts, provided exclusively for your use throughout your stay, making it easy to explore the island and its stunning surroundings.

Interaction with Guests:
We are not on site, but our team is always available to answer any questions you may have or address any issue that arises during your stay. We are here to make your stay perfect!

Property manager

Kate Watt
Premier Host

Languages

English
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Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Air conditioning

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House Rules

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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
1. Check in: After 4pm / Checkout: Anytime before 10am. Late checkout is not permitted; a penalty of $50 per hour per unit will be charged for late...

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Captiva

Located on the beach, this holiday home is in North Captiva, a neighbourhood in Captiva. Barbara Sumwalt Useppa Island Historical Museum and Barbara Sumwalt Museum are cultural highlights, and some of the area's landmarks include Captiva Chapel By the Sea and Boca Grande Lighthouse Museum.
Map
Captiva, Florida

What's nearby

  • North Captiva Island Beach - 1 min walk - 0.2 km

Restaurants

  • The Mucky Duck
  • Tarpon Lodge
  • Starbucks
  • RC Otter's Island Eats
  • Over the Waterfront

Frequently asked questions

Does Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts have a pool?

Yes, this property has a pool.

Is Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts pet-friendly?

No, pets are not allowed at this property.

Where is Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts located?

Within easy reach of North Captiva Island Beach and Cayo Costa Beaches, this Captiva holiday home is located by the ocean and set on the beach. Area attractions also include Cabbage Key and Alison Hagerup Beach Park.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 14 out of 14 reviews
Rating 8 - Good. 0 out of 14 reviews
Rating 6 - Okay. 0 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 0 out of 14 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Daddy A.

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

Amazing!!

Just what we needed!!
Stayed 7 nights in May 2025

10/10 Excellent

Claudette G.

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

North Captiva is paradise!

Accommodations were beautiful! 30 steps to the beach!! Fantastic family vacation!!
Stayed 7 nights in Jun 2022

10/10 Excellent

Thomas K.

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

Breathtaking Views!

This house has it all from the first floor to the third! The house is very well appointed! We will definitely be back!
Stayed 7 nights in Aug 2022

10/10 Excellent

Ted H.

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

5 Star for sure!

Really cool place to take your family. Home is just like the description says.Everyone had an awesome time enjoying this fantastic home and beautiful island. Linda and her crew were great! Thanks
Stayed 7 nights in Mar 2022

10/10 Excellent

Robin M.

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

Paradise

This trip was an amazing experience. Fantastic property on a beautiful island. The pictures don’t do it justice. Life goes at a slower pace on the island and that was exactly what our family needed. We will definitely be back!
Stayed 7 nights in Jul 2022

10/10 Excellent

Michele J.

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

Wonderful Vacation in Paradise

We just returned from our wonderful vacation in North Captiva. Gypsy Wind did not disappoint! Beautiful home with breath taking views! The process of booking, making travel plans and arrival were super easy. Linda, Becca, and Bill were great to work with. Highlights of our trip including daily dolphin sightings, renting a boat and exploring Cayo and Cabbage Key, beautiful sunsets and relaxing with friends. I would definitely recommend Gypsy Wind!
Stayed 7 nights in Jul 2022

10/10 Excellent

Greg D.

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

Wow! Fantastic Week at North Captiva Island at Gypsy Wind.

We just returned from a week's stay, and I can honestly say it was perhaps the best vacation our family has ever experienced. Our group of 11 had ample room to roam, sleep, dine and enjoy exploring the island in the two, six-passenger electric golf carts included with the rental. From start to finish, communication with the property owner and interaction with the onsite Management Team was exceptional. We were even welcomed by a fully-costumed Easter Bunny which was remarkable considering the temperature was in the mid-80's upon our arrival! The private pool, close proximity to the beach and water and the beautifully furnished home created a relaxing and fun-filled week. I highly recommend this property to anyone looking for a spacious and well-kept home surrounded by unspoiled natural beauty. I am certain you will not be disappointed!
Stayed 7 nights in Apr 2022

10/10 Excellent

Peter A.

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

Fantastic Family Vacation

Not even sure where to start! We recently had our family vacation and were lucky enough to stay at Gypsy Wind! This was our second time visiting North Captiva and it was even more magical! From the ease of ordering food, to the seamless pick up at the dock and arrival at the home to the service throughout the week… we could have not asked for more. The house was spectacular and large enough for all of us to gather comfortably or space out as needed! Jim and Linda were so responsive from time of booking to our departure from the house despite dealing with a hurricane in between. Our house was expertly stocked by Antoine and Cale was there all week to answer any questions that we had. We also had a wonderful dinner prepared by Chef Bo. If you are looking to get away from it all, but at the same time enjoy all the comforts of home (and more!) this is the house for you. We look forward to coming back again and again.
Stayed 7 nights in Aug 2023

10/10 Excellent

Pam C.

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

A Slice of Paradise

Gypsy Wind is a beautiful, tranquil, amazing place! You will not be disappointed! I was skeptical and a little scared about how everything would come together: groceries, travel… and Linda, the owner of Gypsy Wind took care of all the details to ensure a hassle free, no stress trip! Linda planned it all out for me and gave me 1 job: to Have the BEST time! And that I did. We cried when we left, we loved it so much! The home is amazing and outfitted with every amenity - the views are spectacular -the pool, warm & inviting, and the beach- the beach is right out the door! Picture yourself going to bed at night listening to the lull of the waves, and waking up to a gorgeous view of the ocean. Honestly, the pictures don’t do the house justice! We already booked next year. I give this place a Super Duper 10 Star Rating! Loved it!
Stayed 13 nights in Mar 2022

10/10 Excellent

Verified traveller

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

Family Vacation

Gypsy Wind is a beautiful property! We felt like we spent a week in paradise. Waking up to the ocean view was priceless! The house had an endless supply of beach supplies which made it easy to load up and spend the day at the beach. The kids and adults loved the pool after our day at the beach. The ice machines were amazing to keep up with our island drinks. The kitchen was stocked for all of our needs. Prior to our visit there were a few things that we requested and the owner was more than happy to supply them for us prior to our arrival. Linda is very accommodating and is very open to any suggestions to make every guests stay enjoyable. We were able to treat our family and grandkids to a meal prepared by Becca, the private chef, and the food was amazing! Enjoying this wonderful meal out on the deck with the ocean view was priceless! Bill, the property manager, was johnny on the spot to help with anything we needed. This was our second stay on the island and would recommend this property to anyone. North Captiva is truly a relaxing piece of paradise!
Stayed 7 nights in Jun 2022

10/10 Excellent

Paul T.

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

Island Paradise with a boat

Absolutely amazing! Took my family on a boat/beach vacation and it became so much more than that. First renting their boat was a great choice. Not only did I get to feel like a guide for the week with that upper station, the package of rods and lures I rented came with local knowledge of how and where to fish. And the fishing was nothing short of remarkable – tarpon, snook, redfish, trout and more. Next about this spectacular house. We were increasing impressed as we first toured the house from the first floor pool area to the second floor, with not one, but 3 master suites. And then finally to the 3rd floor with that spectacular view of the gulf. Morning coffee and sunset views will never be duplicated from that view. The house has too many amenities to mention but our favorites were espresso/cappuccino coffee machine, a chefs kitchen with everything you need, ice makers, kayaks, paddleboards, corn hole, and of course the pool and jacuzzi. Lastly, this island is a hidden paradise. You feel more like you are in the Caribbean than you do in Florida. We had daily tennis and pickle ball tournaments, walked the beach for shells and wishing those turtle nests would hatch. We have never had a vacation like this and we will definitely go back.
Stayed 7 nights in Jul 2023

10/10 Excellent

David G.

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

Hidden Treasure - A Tropical Paradise

Our week here at Gypsy Wind has been nothing short of spectacular. I could (and will) go on and on, so hang in there for a full review! First, I was nervous about staying on an island, worrying it would feel too remote. I was also concerned about staying on an island hit by a hurricane less than a year ago. After fighting my fears and coming anyway, my worries were for naught (as they usually are, right?). With some preplanning for food and other essentials, we’ve had everything we needed. And, when I needed brown sugar for spontaneous cookie baking, Kale (property manager) posted it on the local owners' page; I had two bags of brown sugar at my door in less than 15 minutes! The locals and other guests were all so friendly. Kale is at your service for anything you need, 24/7, which eased my overall concerns. The boat ride from the mainland is less than 30 minutes long, and the water is shallow - mainly 4 feet deep! In addition, North Captiva has medics, a fire department, and a helicopter if there is an emergency. I felt safe here. And, though parts of the island are still recovering from the hurricane, it has not taken away from the experience at Gypsy Wind nor on North Captiva Island. Gypsy Wind’s location is an ideal spot on the island, private and only a stone’s throw away from the beach. The Gulf and sunset views are incredible! The beach is “sugar sand,” white and clean, with more shells than I have seen elsewhere. Unlike many other homes
Stayed 7 nights in Sep 2023

10/10 Excellent

Mary M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in May 2024

10/10 Excellent

Lauren R.

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

Family Vacay

We absolutely loved our stay at Gypsy Wind. The view from the top floor was spectacular, especially during the sunsets! The large kitchen and living area was perfect for our group of 12. They thought of everything from 2 sets of washer/dryers, to little fridges down by the pool, to coffee pots outside your bedroom balcony. Our kids favorite feature was not having to leave the house to go to the pool. Hammocks, games, beach chairs, umbrellas, pool toys - they have it all! We would recommend Gypsy Wind to everyone!
Stayed 7 nights in Jul 2023

About the host

Hosted by Kate Watt

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests