Entire home
Gypsy Wind: Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts
Photo gallery for Gypsy Wind: Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts





Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms4+ bathroomsSleeps 123000 sq ft
Popular amenities
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
Bathtub · Toilet · Shower only
Bathroom 3
Bathtub · Toilet · Shower only
Bathroom 4
Bathtub · Toilet · Shower only
Bathroom 5
Toilet
Spaces
Kitchen
Office
Balcony
Garden
Dining area
About this property
Gypsy Wind: Gulf-Front w/ Heated Pool, Hot Tub & Golf Carts
Summary:
🤝 Local concierge support for a stress-free stay!
🌊 Gulf Front Paradise with oceanside Tiki Bar
🎉 Packed with Fun: Beach gear, pool toys, indoor and outdoor games, kayaks, paddleboards, hammocks & more!
🚗 Two Golf Carts included
🏊♂️ Heated Private Pool and hot tub
🏠 Room for All: 3 king suites, 1 queen, a bunk room, & pull-out couch
🍳 Gourmet Kitchen: Featuring Sub-Zero & Viking appliances.
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.
🎉 Outdoor games and a beachfront hammock for relaxation and fun.
🔥 Two propane BBQ grills—one near the kitchen and one by the 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, on the porch, 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!
🤝 Local concierge support for a stress-free stay!
🌊 Gulf Front Paradise with oceanside Tiki Bar
🎉 Packed with Fun: Beach gear, pool toys, indoor and outdoor games, kayaks, paddleboards, hammocks & more!
🚗 Two Golf Carts included
🏊♂️ Heated Private Pool and hot tub
🏠 Room for All: 3 king suites, 1 queen, a bunk room, & pull-out couch
🍳 Gourmet Kitchen: Featuring Sub-Zero & Viking appliances.
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.
🎉 Outdoor games and a beachfront hammock for relaxation and fun.
🔥 Two propane BBQ grills—one near the kitchen and one by the 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, on the porch, 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!
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning
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9.8 out of 10, Exceptional, (26 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 9:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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. Take the opportunity to explore the area for water adventures such as fishing.

North Captiva, FL
What's nearby
- North Captiva Island Beach - 1 min walk - 0.0 km
Restaurants
- Mainstay North Captiva & Barnacles Bar - 1 min walk
- Mangos
- Starbucks
- The Bubble Room
- Tarpon Lodge Restaurant
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
5 Jun, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in May 2025
10/10 Excellent
Claudette G.
23 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
North Captiva is paradise!
Claudette G.
Stayed 7 nights in Jun 2022
10/10 Excellent
Thomas K.
18 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Breathtaking Views!
Thomas K.
Stayed 7 nights in Aug 2022
10/10 Excellent
Ted H.
22 Mar, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
5 Star for sure!
Ted H.
Stayed 7 nights in Mar 2022
10/10 Excellent
Robin M.
6 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Paradise
Robin M.
Stayed 7 nights in Jul 2022
10/10 Excellent
Lauren R.
16 Jul, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacay
Lauren R.
Stayed 7 nights in Jul 2023
10/10 Excellent
Michele J.
10 Aug, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful Vacation in Paradise
Michele J.
Stayed 7 nights in Jul 2022
10/10 Excellent
Greg D.
27 Apr, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wow! Fantastic Week at North Captiva Island at Gypsy Wind.
Greg D.
Stayed 7 nights in Apr 2022
10/10 Excellent
Peter A.
26 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Family Vacation
Peter A.
Stayed 7 nights in Aug 2023
10/10 Excellent
Pam C.
7 Apr, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Slice of Paradise
Pam C.
Stayed 13 nights in Mar 2022
10/10 Excellent
Verified traveller
23 Jun, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacation
Verified traveller
Stayed 7 nights in Jun 2022
10/10 Excellent
Paul T.
1 Aug, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Island Paradise with a boat
Paul T.
Stayed 7 nights in Jul 2023
10/10 Excellent
David G.
30 Sept, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hidden Treasure - A Tropical Paradise
David G.
Stayed 7 nights in Sep 2023
10/10 Excellent
Leigh G.
24 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy



Leigh G.
Stayed 5 nights in Feb 2026
10/10 Excellent
Michele B.
10 Feb, 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Michele B.
Stayed 7 nights in Feb 2026
10/10 Excellent
Todd S.
25 Oct, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Todd S.
Stayed 7 nights in Sep 2025
10/10 Excellent
Mary M.
31 Jul, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Mary M.
Stayed 7 nights in May 2024
About the host
Hosted by Kate Watt
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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