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  • Exquisite Accommodations and Your Own Fishing Boat!

  • 30 Steps to the Gulf of Mexico

  • ​​3 Master Suites With King Beds & en Suites

  • Three Story Elevator

  • Two Sets of Washers & Dryers

  • Heated Saltwater Pool With Tiki Bar and Outdoor Shower

  • Gourmet Kitchen

  • Two Large Screened-In, Wrap-Around Porches With Jacuzzi

  • Full-Home Clean Water System

  • Two 6-Person Golf Carts

  • 10' BOTE Float 

  • 4 Kayaks, 3 SUPs, Beach Cruiser Bikes, & so much more

Chilling on BOTE float with beverages
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Rent our

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For Your Island Vacation

*Use of the boat is conditional on boating experience. Insurance, Fuel, cleaning fee, and any equipment rentals is an extra fee.

Recent Guest Reviews


Jill A. 
September 2023

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 on the island, G.W. is a beachfront property. Also, I learned how lucky we are to have rented a completely screened-in place. Florida beaches have little bugs called “noseeums,” we weren’t bothered by them while dining on the porches, drinking coffee on the swing, etc. The house itself is luxurious and comfortable, all in one. The three levels are tiled with cozy furniture and throw rugs. The cleanliness is impeccable, and the decor is so tasteful! I am ordering some of the things for my home. The beds are incredibly comfortable, as is the bedding. The rooms are zoned for air conditioning, the bathrooms have bidets, the showers are perfect, and the kitchen is fully equipped, better than our home! Everything I needed to cook for a crowd was here: cookie trays, crock pot, Keurig/coffee pot/Espresso-Latte machine, and enough pots, pans, dishes, glasses, etc. for many! The internet is high-speed, the TV and movie screen are a plus, and there are puzzles and games for rainy days. The beach walks are incredible with shelling, fishing, sand castle building, and a new, extra large party float for guest use that arrived during our stay! The 6 of us hung out in it in the gulf! There are also paddleboards and kayaks. You can also rent their boat. Kale will teach you how to use it. We went to Cayo, a 10-minute ride from here, and did some incredible shelling, including sand dollars! Aside from beach activities, there are several outdoor things to do right at the house, including the pool, Tiki bar, corn hole, Foosball, Ladder Toss, and more! My favorite place to be is on the swinging queen-sized day bed! I went there when I needed a little space from the family and for the Gulf view. We have enjoyed touring the island on the golf cart, visiting manatees, a local swim bar/eatery (Mangos), a gift shop, and getting ice cream! While there are other rentals on the island, we learned while staying here there were extra amenities other rentals don’t offer: transportation to and from the island, boat/dock access, pool, hot tub, two golf carts, screened-in porches, outdoor day bed, and the floating dock with anchor. The organized website helped us be best prepared - be sure to check it out. We did have questions ahead of time, and Linda and Jim were helpful and eased my worries. We don’t want to leave; we will be back! Just do it!


Cheryl H. 
August 2023

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.

Heidi W. 
June 2023

Just returned from a week at Gypsy Wind retreat in North Captiva and a 5 star scale doesn’t come close to measuring the incredible time we spent there!! If you are looking for total relaxation in a top shelf environment you can’t do better than Gypsy Wind. From the owner and property manager communication prior to our travel, to our flawless arrival, they delivered. Antoine Good from. A Good Grocery did our shopping and our order was perfect! The home is impeccably appointed with everything from an elevator to 2 new six passenger golf carts, Viking appliances and a warming drawer in the chef’s kitchen, two sets of washers and dryers (with environmentally friendly ozone system!!) located on pool and living room level respectively as well as refrigerators to accommodate groceries and libations for all your guests!! With 4 huge rooms 3 with en-suite bathrooms) plus a bunk room for the kiddos, 2nd floor hot tub and coffee bar for watching the sunset over the water, smart toilets, spacious bedrooms, bathrooms, board and yard games, 2 kayaks, stand up paddle boards, and pool toys galore you family won’t think about phones, meetings or video games because there is something to do every moment of your stay. Not to mention the entire house smells like a 5 star hotel spa!! We fished, swam, snorkeled, hunted for shells, island hopped, had game and movie nights and saw all kinds of local wildlife (box turtles, rabbits, manatees, tarpon and dolphins, osprey nests, and pelicans) as we explored the island. Most of these could be seen from our 2nd and 3rd floor screened porch overlooking the Gulf of Mexico. There is nothing missing from this home. Handcrafted soap, tropical breezes and the most beautiful sunsets you will see anywhere. Every tool, accessory and cooking implement (and grill) you can think of is here. Both the owners and property manager were accessible anytime we had questions no matter how small. If you are ready for the vacation of a lifetime without the need for a passport- book your stay at Gypsy Wind. You won’t ever want to leave!!

What is a Gypsy Wind ?

A nautical expression for a sailing vessel stocked to the brim with culinary treats for creating stimulating conversation and providing memorable times with special guests.  It also refers to a breeze that swirls and varies in speed and direction as if it follows no rules or customs.

The two meanings wonderfully intertwine to capture the atmosphere of our Island beach home.  A place to entertain guests and enjoy the island life at your own leisurely pace.

We want our guests to know, that when you arrive, we will be stocked to the brim with everything your family and friends need to enjoy this wonderful island paradise.

Bob Seger referenced Gypsy Wind in his song,  
"You'll Accomp'ny Me"
"A gypsy wind is blowing warm tonight
The sky is starlit and the time is right
And still you're tellin' me you have to go
Before you leave there's something you should know..."

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