Gypsy Wind Island Retreat

city of North Captiva Island Vacation Rentals
  • Sleeps 14
  • 5 Bedrooms
  • 4.5 Bathrooms
  • 3000 sqft.

  • Boat Friendly


Exquisite Accommodations and Your Own Fishing Boat or dock for boats up to 26'!

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


  • Balcony
  • Beach Chairs
  • Beach Towels
  • Bicycles
  • Boat
  • Deck / Patio
  • Kayak / Canoe
  • Lawn / Garden
  • Outdoor Furniture
  • Porch / Veranda
  • Tennis
  • Water Sports Gear
  • Books
  • DVD Player
  • Foosball
  • Games
  • Games for Kids
  • Music Library
  • Satellite / Cable
  • Stereo
  • Toys
  • TV
  • Air Conditioning
  • Basic Soaps
  • Bed Linens Provided
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Board
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Baby Gate
  • Internet
  • Living Room
  • Paper Towels
  • Parking
  • RV & Boat Parking
  • Safe
  • Shampoo
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Grill
  • Ice Maker
  • Kettle
  • Kitchen
  • Kitchenette
  • Lobster Pot
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Heated Pool
  • Hot Tub
  • Outdoor Pool
  • Pool
  • Private Pool
  • Spa Whirlpool
  • Boat Friendly
  • Children welcome
  • Elevator
  • Luxury
  • Beach Umbrellas
  • Catering Available
  • Cooking Utensils
  • Dining Area
  • Dock
  • Fish Cleaning Table
  • Freezer
  • Golf Cart
  • Hot Tub Spa
  • Jetted Bath Tub
  • Lanai / Gazebo
  • Netflix
  • Outdoor Gas Grill
  • Picnic Table
  • Terrace / Balcony

Location Info

Gypsy Wind is located on. North Captiva Island, a barrier island off the coast of southwest Florida that is only accessible by boat or ferry. It is not Captiva, FL which is located to the South separated by Redfish Pass, a body of water that you do not want to try to drive a car across. North Captiva is 4 miles long, with the northern 1 mile is where most homes are built, this is often referred to as Upper Captiva. The island has no supermarket, no fuel dock, three restaurants and miles of quiet sand beaches. No cars are allowed on the island, so golf carts and bikes are the main means of transportation. This is true secret jewel on the Florida Coast that harkens back to simpler times.


Nightly rates range from $1,100.00 to $2,300.00


About Owner

Gypsy Wind is owned by a brother and sister, John & Linda, and Linda's husband, Jim. After four months of searching over one hundred properties all over Florida, something kept drawing us back to this little island called North Captiva. Like many, we had heard of Captiva and Sanibel but had never heard of this island. Then, we visited North Cap. From the moment we stepped off the boat, we knew this place was different. It felt more like a Caribbean Island than Florida. Quiet, relaxed, and far from the tourist traps. Then we saw the home in person, and we knew the search was over. The pictures are impressive, but in person, the home is an absolute stunner.We are delighted to share this with our guests looking for an exceptional home...

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Check-In Time : 04:00 PM
Check-Out Time : 09:00 AM
  • Suitable for Children

General Policies

Do not leave doors and windows open while HVAC is runningNo glass in pool areaChildren under 16 must have an adult supervising them while in pool or hot tub area. No playing of loud music after 10pm at nightNo outdoor lights on after 10pm from May 1 - Aug 31stDo not drive golf carts on beach or through puddles. Please rinse carts with hose if they must travel through waterNo one under 16 may drive the golf carts, any accidents will be the liability of the renter No fish allowed in the upstairs refrigerator, please store all seafood in the downstairs refrigerator The elevator is not a toy and is ONLY for those who need it or to bring items up and down. Children are not to use it without an adultThe Sonos move speakers are not ...

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House Rules

The home has a maximum of eight (8) adults, 21+ yr olds, and six (6) children under age 21 are allowed during a one week stay. At no point can the home be occupied more than the maximum. GYPSY WIND abides by all night sky and turtle friendly guidelines for evening lights and removal of any beach equipment each evening.The pool and spa heat are controlled by the owners, any request for a change in temperature must be requested with the property manager.The home is outfitted with luxury items for the kitchen, dining area, and pool. Please report any damage or accidents so that we can repair or replace items for the next guests.North Captiva does not have life guards so all beaches are swim at your own risk. This also applies to overseeing chi...

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Terms & Conditions

Cancellation Policy

  • 50% of the total stay fee will be required upon confirmation of the reservation. The final 50% will be charged 60 days before the first day of the guests arrival. 
  • CANCELLATION POLICY if guests cancel prior to 60 days a 100% refund will be granted.

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