House in North Captiva Island, FL
8 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
Turquoise water skips beneath you, music on the breeze, as the ferry pulls into the dock at North Captiva Island. Your island management team is waiting - and before you know it, you're zipping off to discover everything Tipsy Turtle has in store: a swim-up tiki bar, heated pool & hot tub, 360° rooftop views, two golf carts, an elevator, beach gear, hammocks, and four sun-soaked decks. Congratulations - you've found one of the best teams and finest properties on this idyllic little island.
NEW TO NORTH CAPTIVA ISLAND? Here's what makes it unforgettable:
North Captiva is one of Florida's last truly unspoiled barrier islands — no roads, no bridges, no drive-up convenience. That's exactly what makes it so magical, and a little planning goes a long way.
Getting here: Guests arrive by ferry, chartered boat, private boat, or small private aircraft. The journey across the water is the first signal that you've left the ordinary world behind. Our property management team meets you at the dock and escorts you to Tipsy Turtle by golf cart - two 4-person golf carts are included with your rental for the week.
Provisioning: There are no major grocery stores on the island. Guests shop on the mainland before boarding the ferry or choose a personal grocery shopper who will have everything waiting for you. It takes a bit of planning, but it's worth it because when you arrive, you can just have fun!
We've got you covered: Once your reservation is confirmed, you'll receive our Digital Guidebook — a step-by-step resource that walks you through planning logistics, our recommended companies, the property's amenities, and island activities. And any time you have questions, Molly and our property manager Kale are always happy to help. -Hosted by Cowboys & Mermaids Vacation Rentals
ABOUT THIS PROPERTY
Outdoor Details: The Thirsty Turtle Bar is the heart of it all. There is nothing else like it on NCI — a swim-up tiki bar and you don’t have to fight the crowds! Belly-up to the bartop, in the heated pool, as you’re handed a freshly blended tropical drink. The music is playing. The group has gathered. Nowhere to be, and no reason to leave.
The pool and hot tub run 24 hours a day and no one’s going to tell you your swim session is over. Outdoor dining for 8, a Weber grill, and an outdoor shower round out the lower deck. Two hammocks, cornhole, beach chairs, umbrella, and a cooler round it all out.
Bedroom/Bath/Deck Details: The home sleeps 8 across three thoughtfully designed spaces. The main-floor bedroom has a queen bed and set of bunk beds and sits conveniently beside the kitchen and a 3/4 bath - ideal for guests who prefer everything on one level. Upstairs, the primary suite features a king bed, a stunning custom bathroom with ample counter space and a double-headed shower, and direct access to a private deck. The second upstairs bedroom offers a queen bed plus a set of bunk beds, an attached full bath, and its own private deck with a spiral staircase that leads straight up to the crow's nest.
Kitchen Details: The open concept kitchen is built for real cooking: A full suite of pots, pans, and bakeware. Drip and Keurig coffee makers, blender, crockpot, griddle, toaster, and reverse osmosis water at the tap. A dining table for 8 with additional spots at the bar stools.
Inside Living: Smart TVs with Roku in the living room and primary suite. Starlink WiFi throughout. Families with little ones will find a pack-n-play, high chair, and a baby gate available. An elevator connects the ground level to the main floor for guests with limited mobility and for luggage. Everything is already here — you just show up.
LOCATION & WHAT'S NEARBY
North Captiva Island is its own world — miles of sandy beaches and tropical vegetation, no roads, no cars, no crowds and no highrise hotels. Your golf cart and bikes are the only transportation you'll need.
BEACH: Your members-only beach access (Captiva Castaway)puts you steps from some of the Gulf's most pristine shoreline: warm, calm water, soft white sand, and shelling that has guests filling bags with whelks, conchs, and sand dollars. Dolphins appear regularly just offshore — early morning walks on the beach often come with a show.
NATURE: Tipsy Turtle is located within the island's sheltered interior which offers something the exposed ocean-front properties can't: the hush of lush tropical canopy, gentle breezes, birdsong, and the kind of quiet that reminds you why you needed this retreat. Zoom off to the 600 acre nature preserve for more nature or head to the docks and beaches to spot manatees and dolphins!
WATER ADVENTURE: Pine Island Sound has some of Southwest Florida's most productive fishing waters — snook, redfish, and tarpon are prized catches. Kayaking and paddleboarding through the mangrove-lined backwaters is a peaceful alternative to the open beach.
BOATING EXCURSIONS: For guests who want to explore the surrounding barrier islands, Boats and Fun on North Captiva rents private vessels for day excursions or, we can recommend a private captain. And at the end of every adventure, Tipsy Turtle is right where you left it — tiki bar ready, hammocks swaying, pool ready for a float.
RESTAURANTS/PUBLIC POOL/SHOPS: Hop on a golf cart - you're only 8 min (or less) from these island establishments: Barnacles/Mainstay - enjoy cold drinks, fresh seafood, and Old Florida charm. Over The Waterfront offers an intimate dinner experience on the water, with delicious food and views of Safety Harbor (reservations required). Mango's Bar & Grill at the Island Club keeps it casual with poolside bites. Make an afternoon of it and enjoy their public pool. The Island Market rounds things out with coffee, ice cream, grab-and-go items, and island gifts.
WHO THIS HOME IS BEST FOR
Families with kids — Tipsy Turtle was designed with families in mind. The pool is fenced, heated, and has a shallow toddler-splashing section. The bunk beds are always a hit, and the world-class shelling keeps kids busy for hours. Pack-n-play, high chair, and baby gates are already here.
Multi-generational families — The elevator, main-floor bedroom, and multiple living spaces make it easy for every generation to be comfortable. Grandparents and grandkids under the same roof, with plenty of room to spread out.
Groups & friend reunions — Four decks, a swim-up tiki bar, outdoor dining for 8, and a crow's nest for sunset toasts. Tipsy Turtle was made for the kind of trip people talk about for years.
Boaters — Many guests bring their own boat. Our team helps arrange your boat slip rental.
Private pilots — Tipsy Turtle holds a North Captiva airstrip membership. Fly in, land, golf cart to your door.
GUEST ACCESS
Everything here is yours: the home, the heated pool and hot tub, the swim-up tiki bar, the BBQ and outdoor dining, two golf carts, beach chairs & beach umbrella.
From the moment you arrive, our property management team is there for you. They meet you at the dock, escort you by golf cart, help carry groceries & luggage up, and get you settled — your vacation starts the moment you step off the ferry.
All property perks and details found within your digital guidebook. Check-in 4PM / check-out 9AM. Security cameras monitor the exterior entrances to the property only.
HOUSE RULES
Maximum occupancy is 8 guests. NO pets. No smoking anywhere on the property, including outdoor areas. No events or parties. Quiet hours are 10PM to 8AM NCI is a peaceful island with a tight-knit community. Must be 24+ to book.
Rental Agreement must be signed within 48 hours - your reservation isn't confirmed until returned. Damage protection via Rental Guardian included (no additional fee).
No one without a valid driver's license may drive a golf cart. No driving golf carts on the beach or in the nature preserve.
The pool and hot tub is for guest use at your own risk. There is no lifeguard on duty. Children must be supervised by an adult at all times while in or around the pool.
NEW TO NORTH CAPTIVA ISLAND? Here's what makes it unforgettable:
North Captiva is one of Florida's last truly unspoiled barrier islands — no roads, no bridges, no drive-up convenience. That's exactly what makes it so magical, and a little planning goes a long way.
Getting here: Guests arrive by ferry, chartered boat, private boat, or small private aircraft. The journey across the water is the first signal that you've left the ordinary world behind. Our property management team meets you at the dock and escorts you to Tipsy Turtle by golf cart - two 4-person golf carts are included with your rental for the week.
Provisioning: There are no major grocery stores on the island. Guests shop on the mainland before boarding the ferry or choose a personal grocery shopper who will have everything waiting for you. It takes a bit of planning, but it's worth it because when you arrive, you can just have fun!
We've got you covered: Once your reservation is confirmed, you'll receive our Digital Guidebook — a step-by-step resource that walks you through planning logistics, our recommended companies, the property's amenities, and island activities. And any time you have questions, Molly and our property manager Kale are always happy to help. -Hosted by Cowboys & Mermaids Vacation Rentals
ABOUT THIS PROPERTY
Outdoor Details: The Thirsty Turtle Bar is the heart of it all. There is nothing else like it on NCI — a swim-up tiki bar and you don’t have to fight the crowds! Belly-up to the bartop, in the heated pool, as you’re handed a freshly blended tropical drink. The music is playing. The group has gathered. Nowhere to be, and no reason to leave.
The pool and hot tub run 24 hours a day and no one’s going to tell you your swim session is over. Outdoor dining for 8, a Weber grill, and an outdoor shower round out the lower deck. Two hammocks, cornhole, beach chairs, umbrella, and a cooler round it all out.
Bedroom/Bath/Deck Details: The home sleeps 8 across three thoughtfully designed spaces. The main-floor bedroom has a queen bed and set of bunk beds and sits conveniently beside the kitchen and a 3/4 bath - ideal for guests who prefer everything on one level. Upstairs, the primary suite features a king bed, a stunning custom bathroom with ample counter space and a double-headed shower, and direct access to a private deck. The second upstairs bedroom offers a queen bed plus a set of bunk beds, an attached full bath, and its own private deck with a spiral staircase that leads straight up to the crow's nest.
Kitchen Details: The open concept kitchen is built for real cooking: A full suite of pots, pans, and bakeware. Drip and Keurig coffee makers, blender, crockpot, griddle, toaster, and reverse osmosis water at the tap. A dining table for 8 with additional spots at the bar stools.
Inside Living: Smart TVs with Roku in the living room and primary suite. Starlink WiFi throughout. Families with little ones will find a pack-n-play, high chair, and a baby gate available. An elevator connects the ground level to the main floor for guests with limited mobility and for luggage. Everything is already here — you just show up.
LOCATION & WHAT'S NEARBY
North Captiva Island is its own world — miles of sandy beaches and tropical vegetation, no roads, no cars, no crowds and no highrise hotels. Your golf cart and bikes are the only transportation you'll need.
BEACH: Your members-only beach access (Captiva Castaway)puts you steps from some of the Gulf's most pristine shoreline: warm, calm water, soft white sand, and shelling that has guests filling bags with whelks, conchs, and sand dollars. Dolphins appear regularly just offshore — early morning walks on the beach often come with a show.
NATURE: Tipsy Turtle is located within the island's sheltered interior which offers something the exposed ocean-front properties can't: the hush of lush tropical canopy, gentle breezes, birdsong, and the kind of quiet that reminds you why you needed this retreat. Zoom off to the 600 acre nature preserve for more nature or head to the docks and beaches to spot manatees and dolphins!
WATER ADVENTURE: Pine Island Sound has some of Southwest Florida's most productive fishing waters — snook, redfish, and tarpon are prized catches. Kayaking and paddleboarding through the mangrove-lined backwaters is a peaceful alternative to the open beach.
BOATING EXCURSIONS: For guests who want to explore the surrounding barrier islands, Boats and Fun on North Captiva rents private vessels for day excursions or, we can recommend a private captain. And at the end of every adventure, Tipsy Turtle is right where you left it — tiki bar ready, hammocks swaying, pool ready for a float.
RESTAURANTS/PUBLIC POOL/SHOPS: Hop on a golf cart - you're only 8 min (or less) from these island establishments: Barnacles/Mainstay - enjoy cold drinks, fresh seafood, and Old Florida charm. Over The Waterfront offers an intimate dinner experience on the water, with delicious food and views of Safety Harbor (reservations required). Mango's Bar & Grill at the Island Club keeps it casual with poolside bites. Make an afternoon of it and enjoy their public pool. The Island Market rounds things out with coffee, ice cream, grab-and-go items, and island gifts.
WHO THIS HOME IS BEST FOR
Families with kids — Tipsy Turtle was designed with families in mind. The pool is fenced, heated, and has a shallow toddler-splashing section. The bunk beds are always a hit, and the world-class shelling keeps kids busy for hours. Pack-n-play, high chair, and baby gates are already here.
Multi-generational families — The elevator, main-floor bedroom, and multiple living spaces make it easy for every generation to be comfortable. Grandparents and grandkids under the same roof, with plenty of room to spread out.
Groups & friend reunions — Four decks, a swim-up tiki bar, outdoor dining for 8, and a crow's nest for sunset toasts. Tipsy Turtle was made for the kind of trip people talk about for years.
Boaters — Many guests bring their own boat. Our team helps arrange your boat slip rental.
Private pilots — Tipsy Turtle holds a North Captiva airstrip membership. Fly in, land, golf cart to your door.
GUEST ACCESS
Everything here is yours: the home, the heated pool and hot tub, the swim-up tiki bar, the BBQ and outdoor dining, two golf carts, beach chairs & beach umbrella.
From the moment you arrive, our property management team is there for you. They meet you at the dock, escort you by golf cart, help carry groceries & luggage up, and get you settled — your vacation starts the moment you step off the ferry.
All property perks and details found within your digital guidebook. Check-in 4PM / check-out 9AM. Security cameras monitor the exterior entrances to the property only.
HOUSE RULES
Maximum occupancy is 8 guests. NO pets. No smoking anywhere on the property, including outdoor areas. No events or parties. Quiet hours are 10PM to 8AM NCI is a peaceful island with a tight-knit community. Must be 24+ to book.
Rental Agreement must be signed within 48 hours - your reservation isn't confirmed until returned. Damage protection via Rental Guardian included (no additional fee).
No one without a valid driver's license may drive a golf cart. No driving golf carts on the beach or in the nature preserve.
The pool and hot tub is for guest use at your own risk. There is no lifeguard on duty. Children must be supervised by an adult at all times while in or around the pool.
Amenities at Swim-up Tiki Bar, Hot Tub, Elevator, Golf Carts
Non-smoking
No pets allowed
Family friendly
Map of North Captiva Island, FL
Ratings and reviews
10 / 10Outstanding·Apr 2025
We had a wonderful stay at the Tipsy Turtle on North Captiva Island in April 2025! The house was very clean, and the owner’s communication leading up to our trip was excellent — the guidebook they provided made everything so easy. Kale Dudding, the property manager, was incredibly attentive and helpful throughout our stay. Check-in and check-out were smooth and stress-free. Our kids absolutely loved the pool, and it quickly became one of the highlights of our trip. We’ve always loved North Captiva Island, and the Tipsy Turtle made our time there even more special. We would definitely recommend it to anyone looking for a great getaway!
10 / 10Outstanding·Apr 2025
We loved our stay at Tipsy Turtle!! The views, the home, the pool, we loved all of it!!
10 / 10Outstanding·Mar 2025
Everything was exactly as described and no surprises. I loved the welcome app and all the helpful tips. It was our first time to the island and we felt properly prepared. The property manager Kale was excellent. Thanks for a great week.e was on it. or
6 / 10Average·Jul 2022
The house is very beautiful and comfortable. The view from the third floor is breathtaking. Clean rooms and bathrooms. We couldn't use the oven in the kitchen because there was a lot of grease on the bottom and when we heated it up a lot of smoke came out and the fire alarm went off. The big grill looked like new but it didn't have enough fire to cook the meat, it probably had the gas vents clogged, a maintenance and cleaning would solve the problem. We used an old and small grill that was going to the dump and we made our barbecue since the house oven had grease on the bottom. Need more comfortable barbecue area, there was only the grill in a sandy area, no lighting and no sink to help. Kitchen needs more supplies like, pan, wine glasses etc
$$$$
Top rated by guests
9.8Outstanding
(24 Ratings)
"We had a wonderful stay at the Tipsy Turtle on North Captiva Island in April 2025! The house was very clean, and the owner’s communication leading up to our trip was excellent — the guidebook they pro..."
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