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Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage

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Luxurious Gulf Experience
Sunset decks
Swinging Queen Daybed
Island Beach Retreat
Rent our 23' Dorado
Reviews
10

Exceptional

5 bedrooms4+ bathroomsSleeps 14279 sq m

Popular amenities

  • Hot tubHot tubHot tub
  • KitchenKitchenKitchen
  • Barbecue grillBarbecue grillBarbecue grill
  • PoolPoolPool
  • WasherWasherWasher
  • DryerDryerDryer

Check out the area

Map
Upper Captiva, FL
  • Popular LocationNorth Captiva Island Beach1 min walk

Rooms & beds

5 bedrooms (sleeps 14)

Flamingo Suite

1 King Bed

Palm Suite

1 King Bed

Reef Suite

1 King Bed

The Dolphin Grotto

2 Single Bunk Beds

The Tarpon Lodge Room

1 Queen Bed

4 bathrooms, 1 half bathroom

3rd Floor

Toilet · Shower only

Flamingo en suite

Toilet · Shower only

Ground Floor Bath

Toilet

Palm en suite

Toilet · Shower only · Jetted bathtub

Reef en suite

Toilet · Shower only

Tiki Shower

Outdoor shower

Spaces

Deck or patio
Kitchen
Balcony
Outdoor play area
Garden
Dining Area

About this property

Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage

Stunning views of sunset and superior craftsmanship combine with casual elegance in this reverse floor plan beach home, designed by a noted Florida architect. This custom ultra-luxury vacation home has everything your family and friends could ever want in a memorable island retreat.

THE ISLAND

People are far more familiar with Sanibel and Captiva, but North Captiva, cut off from her sister island to the south 100 years ago, couldn't be more different. There are no cars, no crowds, a few restaurants, 4 miles of spectacular beaches, friendly families, and abundant wildlife.

Typically visitors are responsible for their own transportation from the mainland to North Cap via the public ferry. However, Gypsy Wind Guests are treated differently right from the start, you and your guests will be arrive on the Island by a private charter from one of our Captains. And that just the beginning of your special experience at Gypsy Wind. Your food order is done ahead of time (there are no supermarkets on the island) and your home will be stocked upon your arrival. Our Home's manager, Kale, will meet you at the boat and bring you to the home where a short introduction to the house. Gypsy Wind is a smart home managed via touch pads on each floor that allow for light, audio, and AC controls. The Home has 5 climate zones you can program to meet everyone's special temperature requests. To get around the island, we have two sux passenger electric golf carts, 2 E-bikes with fat tires to explore the WHOLE island, 2 beach cruiser bikes, or your own flip-flop feet. Our crew takes pride in making sure your equipment and gear is all running well and ready for you when you arrive.

GETTING TO NORTH CAP

Fly into Ft Myers airport (RSW), and a taxi or car service will bring you to Captain Cons Marina to deliver you out to this barrier island. Our greeter will meet you when you arrive at Captain Cons and show you and your guests everything about the island and our home. The cost of a round-trip private boat charter (on and off) to North Captiva Island is included in your trip.

When you enter the property, the manicured grounds and attention to every detail are evident. Stepping into the foyer, you'll be impressed by the bamboo craftsmanship of the stair railings. The bamboo was sourced from the South Pacific and hand-crafted by the same team that built much of Disney's Polynesian decor. There is an elevator with the same bamboo design elements to help those who might struggle with the 3 flights of stairs or make carrying bags upstairs much easier.

The 2nd Floor showcases three stunning Master Suites with en suite bathrooms with exceptional views right from the Tommy Bahama King Beds. The Palm Suite, the largest of the three, includes a walk-in closet, spacious bathroom with dual head tiled shower, double vanity, and jet tub with views of the Gulf. The Reef & Flamingo Suites are similarly furnished, and every bathroom in the home has shampoo, conditioner, and our Gypsy Wind handmade soap. All three Suites have "smart" toilets that add "next-level" luxury to your stay. The three Suites have access to the wrap-around screened-in porch complete with nap-inducing chaises and chairs. The porch also includes a coffee bar, a mini fridge for early morning risers, and a hot tub, the ideal spot to watch those epic Gulf sunsets. On the 1st floor are the final two bedrooms; the Tarpon Room has a queen bed and the Dolphin Grotto has a triple bunk bed, and later this summer will have an additional fold-down triple bunk. Complete with a projection screen that emerges from the ceiling. Any device can stream movies or games for the kiddos.

The 3rd floor is the main floor for dining and hanging out. It features a dramatic open-plan living space with bamboo accent trim. The west-facing wall has floor-to-ceiling French doors and windows, with dramatic, angled windows taking full advantage of the views. Just through the French doors is the covered screen porch with views that will take your breath away. Back inside, if you need to look at something else, and why would you :) the home's new 4K 80" Smart TV to watch the big game on the home's Starlink service, or you can connect to your own Netflix or streaming provider. If you'd rather listen to music, connect to the home's Sonos speakers throughout the living areas. Listen to Jimmy Buffet on the 3rd-floor porch while others can listen to their music in the pool area.

The foodie and chefs in your party will enjoy cooking in our Gourmet Kitchen. It is outfitted with Viking appliances and restaurant-sourced frying pans, pots, a paella pan, a limitless collection of knives, cooking utensils, and a pantry stocked with essential cooking oils, spices, and basic baking ingredients. No kitchen would be complete on North Cap without ice machines and wine fridges! Gypsy Wind has two! One is conveniently located in the kitchen, and the other in the pool area is a large new commercial Manitowoc Ice Machine that can produce up to 385lbs/day! There is also a 32' Blaze grille just off the kitchen area and another grille in the pool area. Just behind the kitchen, you'll find another full bathroom and laundry room that comes complete with laundry detergent suitable for our home's septic system.

The ground floor has a heated pool and tiki bar, making it the perfect place to enjoy afternoon lunch, BBQ dinner on the 6-burner grill, or late-night cocktails under the stars. The Tiki Bar has been renovated and now includes a blender, Margarita maker, and ice crusher for making those frosty cocktails or snow cones for the kids. All plastic serving items are stored inside the 1st-floor pool entrance and may be cleaned using the 1st-floor dishwasher for easy clean-up. You'll also find another new washer/dryer for managing the pool & beach towels and all of those wet bathing suits.

Enjoy the water During your stay using the home's two stand-up paddleboards or two-person kayaks. A variety of safety items, including a supply of life jackets for adults and children; if your child uses a particular swimming safety item, please bring those with you. The roads on the island are sandy paths, and our carts are built specifically for this terrain. Since only electric golf carts are allowed, having a well-charged golf cart is a MUST. For this reason, Gypsy Wind has invested in fast-charging and long-lasting lithium batteries. The LED readout on the dash tells you exactly how much power is remaining. Plug the carts in for a few hours, and you are fully ready for more exploring. ONLY Licensed drivers are allowed to drive the carts.

If you want to explore Pine Island Sound's waters, rent a boat from www.GypsyWindboatrental.com. Our 23' Dorado with second station, live well, SIMRAD navigation, fishing rod packages, paddle boards, bean bag chairs, and so much more is only rented to our guests and is docked at Safety Harbor Wharf.

If you want to bring your own boat, we can procure you a slip at Safety Harbor Club dock for boats under 26' for an added weekly fee. You must request your slip along with the boat's information so we may register your dockage at least two weeks before your arrival.

Our rental period for check-in and check-out is from Sunday to Sunday. The reason? Nearly every rental property rents from Saturday to Saturday, and the island's docks, ferries, and resources can be a bit chaotic. We want you to have only the finest experience so we avoid the Saturday crowd, and you have our teams' complete dedication and availability. Please do not hesitate to call us for any details about the home or your stay.

Property manager

Linda McDonald

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Free WiFi

House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 9:00 AM

Children

Children allowed: ages 0–17

Events

Events allowed
Small Family gatherings, maximum 8 Adult guests. N

Pets

No pets allowed

Smoking

Smoking is not permitted
A security DEPOSIT is required prior to arrival of $10,000 and automatically released 7 days after checkout unless an issue is found.
Guests MUST sign the Rental Agreement to finalize their rental opportunity
Sorry, we do not accept American Express

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

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
Parties and events are allowed on site
Note from host: Small Family gatherings, maximum 8 Adult guests. N
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

We should mention

A car is not required for transport to and from this property

About the area

Captiva

Located on the beach, this holiday home is in North Captiva, a neighbourhood in Captiva. Calusa Heritage Trail and McCarthy's Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sanibel Island Southern Beach and Alison Hagerup Beach Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Upper Captiva, FL

What's nearby

  • North Captiva Island Beach - 1 min walk

Restaurants

  • The Mucky Duck
  • Tarpon Lodge
  • Mango's - 12 min walk
  • Doc Ford's Rum Bar and Grille - Captiva Island
  • Starbucks

Frequently asked questions

Is Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage?

Check-in begins at 4:00 PM.

What time is check-out at Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage?

Checkout is at 9:00 AM.

Where is Luxurious Gem on Gulf, Heated Pool, Hot Tub, Tiki Bar, Elevator, Boat & Dockage located?

This North Captiva holiday home is on the beach, 0.1 mi (0.1 km) from North Captiva Island Beach, and within 6 mi (10 km) of Alison Hagerup Beach Park and Captiva Beach. Turner Beach and Blind Pass Beach are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 22 out of 22 reviews" "
Rating 8 - Good. 0 out of 22 reviews" "
Rating 6 - Okay. 0 out of 22 reviews" "
Rating 4 - Poor. 0 out of 22 reviews" "
Rating 2 - Terrible. 0 out of 22 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

About the host

Hosted by Linda McDonald

Host profile image
Hi, we're Linda, Jim, and John. We purchased the home as a new vacation investment property but after spending time on the island and getting to know the home it has become so much more. This is now our home away from home and we want our guests to feel the same. Everything we buy for the home is something we want to use and share with friends and rental guests.

When we began our search for a vacation home in Florida, the home needed to be close to the water and have a certain, let's just say energy. It must be inviting, comfortable, well-crafted, and most of all fun. This wasn't simply a business purchase but a place where our family would enjoy visiting as much as our weekly guests.

Why they chose this property

After four months of searching, over one hundred properties all over Florida, that energy we mentioned, kept drawing us back to this little island we'd never heard of before. Like many, we had heard of Captiva and Sanibel but had never heard of North Cap. and something stood out about it. Beautiful craftsmanship, yet, warm and inviting. It was a home, not just a generic vacation property. But pictures can be deceiving so we flew down to see it. As we stepped off the boat onto North Captiva, we both had chills. This place was different. It felt like a Caribbean Island...but only requires a short plane ride, and no passport.

Then we saw the home. Our decision was made. We had found it. While the pictures are impressive, in person, the home is an absolute stunner. The home has never been rented, and the two previous owners took such exceptional care of it that we feel a sense of obligation to keep it at the highest standards. We are delighted to share this with our weekly guests looking for an exceptional home that sits on the Gulf of Mexico. We hope you can create your family's lifetime memories at our new home, Gypsy Wind.



Best,

​Linda, John & Jim

What makes this property unique

Being just 30 steps from the Gulf Waters is both beautiful and convenient. Being so close also means not having to pack every little thing to go to the beach. We do provide a new beach wagon to carry your chairs and maybe a cooler with some drinks, but you don't need to worry about bathroom breaks or going back to put a little one down for a nap. Continuing with the home's convenience is the home's elevator for easy access to all floors. Gypsy Wind's furnishings and decor are 'island casual' with a stylish Tommy Bahama flair. We have purchased many new items for the pool area and Tiki bar...new pictures will be appearing in the coming weeks. Our guests have use of two (2) lithium battery-powered 6 person golf carts with a fold-down rear seat and USB charging port. Gypsy Wind also provides two new tandem kayaks and two Bic stand-up paddleboards, all of the beach gear you may need for your family including chairs, umbrellas, a beach wagon, games, blankets, and beach towels.
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