Holiday rentals with a pool in North Captiva Island

The exterior of the home displays a modern design with a light color palette. A set of wooden stairs leads to the entrance, surrounded by lush palm trees and verdant foliage, providing a tropical ambiance. Clear blue skies create a bright backdrop.

5.0 out of 5 average rating, 19 reviews

Gumbo Limbo North Captiva

Located on North Captiva, in Safety Harbor Club, this comfortable home is conveniently located near beaches, pools, & boat docks. Nestled among native palms, Gumbo Limbo has a wildlife-friendly, private setting you will love. Beautiful beaches & refreshing pools are a short walk or 2 minutes by golf cart (included). The island has over 5 miles of pristine sandy beaches to explore. 3 large pools, tennis & pickle ball courts, sea kayaks, bicycles & private beach access are available to guests.

A scenic view showcases a private deck featuring a spa and circular seating area, positioned near lush greenery. The serene beach is visible in the background, leading to calm waters under a softly lit sky at sunset, creating a tranquil coastal atmosphere.

4.96 out of 5 average rating, 49 reviews

Beachfront North Captiva | Rooftop Deck | Hot Tub

No bridges. No cars. No crowds. Stella Maris sits directly on the Gulf on North Captiva — a private barrier island reachable only by boat. Step off your deck onto white sand. Watch dolphins from your 360° rooftop deck at sunset. 3 bedrooms, each with private en-suite bath. Cathedral ceilings, gourmet kitchen, formal dining with Gulf views, stone fireplace, hot tub, and included golf cart. Dual club access — Safety Harbor Club included; optional Island Club for pools, kayaks, bikes, and pool bar.

A bird's-eye view captures a modern two-story home with a metal roof surrounded by lush tropical landscaping. A large heated swimming pool is seen in the foreground, with lounge chairs positioned nearby, emphasizing outdoor relaxation in a serene setting.

5.0 out of 5 average rating, 22 reviews

" Here Comes The Fun" Absolutely Magnificent! Home

HERE COMES THE FUN! Doo-d-Doo-Doo FUN FUN FUN HERE IT COMES! No detailed has been missed. This is truly a luxury home. HERE COMES THE FUN is a single story 3-bedroom, 3.5 bathroom home. Finished in early 2020 it was built on 2.5 lots or on one half acre of sand. Its location is only a 3.5-minute walk on a white sand path-like road past just 4 houses to the largest beach on the island. There is public access and golf cart parking available there and that isn’t always the case on other streets.

A modern beach house is elevated above the ground, featuring a sleek metal roof and large windows. The outdoor space includes a sparkling pool surrounded by tropical landscaping, with lounge chairs positioned nearby for relaxation.

5.0 out of 5 average rating, 17 reviews

Waid N Sea-Sprawling Gorgeous Beach House/Pool/Bar

Welcome to the Gorgeous Brand New "Waid N Sea" Beach House! Located on the Barrier Island of North Captiva, this 4 BR, 3 Full Bath, Private Heated Pool Home with Amazing Outdoor Dining and Entertaining Areas is now booking Simply Luxurious Vacation Stays! Temporary Boat Dockage may be available inquire! This Superb Beach House located only steps to the most desirable "Butterfly Beach" offers White Sugar Powdered Sand, Amazing Gulf Ocean Views and Wildlife, and World Class Fishing and Shelling!

A two-story beach house features a bright blue exterior and large windows, surrounded by palm trees and lush greenery. A wooden staircase leads to the entrance, with a deck visible on the upper level. The sandy area offers a welcoming beach environment.

4.91 out of 5 average rating, 138 reviews

Blue Laguna - Vacation in paradise!

This bright, fully equipped welcoming three‑story home features a private heated pool and a rooftop observation deck with stunning 360‑degree water views. It offers three comfortable bedrooms and three full bathrooms for up to six guests, plus two screened lanais where you can relax in the island breeze and listen to the birds. A four‑seater golf cart is included, so you can easily explore the beaches and sandy paths of beautiful North Captiva Island. Also full access to Island Club amenities!

A comfortable outdoor seating area features a large sectional sofa adorned with decorative cushions. A coffee table is centered on a patterned rug. In the background, a private pool is visible through a white fence, surrounded by lush greenery.

5.0 out of 5 average rating, 18 reviews

Island paradise. Hakuna Matata.

Our car-free paradise is a destination like no other. Only steps to the beach, Hakuna Matata provides the perfect escape. The home is complete with marble floors throughout, a granite kitchen and minibar, 3 bedrooms and 2 bathrooms. We have two king beds, a queen, and triple bunks. An entertainment area is complete with a private pool, sitting area, pool table and ping pong table, television, outdoor games, a grill, and an outdoor shower. Two golf carts are provided for your stay to explore.

4.8 out of 5 average rating, 86 reviews

A beach cottage-style home is elevated on stilts, surrounded by lush palm trees. The exterior features a light-colored facade, large windows, and a balcony with railing on the upper level. A clear blue sky serves as the backdrop, enhancing the overall coastal atmosphere.

Cottage in Captiva

Turtle Trax

Welcome to paradise! Your stay includes The Island Club access to clubhouse pools, pool bar, hot tub, as well as bikes, kayaks, and tennis and basketball fun. There is a 4-seater golf cart included for everything you need to make your vacation a memorable one. All your linens, fully equipped kitchen, private pool with screened in pool deck, propane grill, central a/c, and streaming TVs are all provided. Games and books for all ages. Hammocks & comfortable beds await your island getaway.

5.0 out of 5 average rating, 23 reviews

NamaStay - Luxury 4BR w Private Heated Pool

Nama-Stay is located on a barrier island in southwest Florida. In fact, the only way to get to the island by boat or private plane. This is THE spot for a relaxing beach vacation. Enjoy your own private heated pool along with all the amenities that are offered by the island's private club. The house also comes with two golf carts so you can easily explore all the island has to offer. This house is a 30 second golf cart ride to the Island Club and a 1 minute golf cart ride to beach access!

The exterior of the beach house is showcased, featuring a covered porch with wooden railings and an American flag. Tropical palm trees surround the property, and stairs lead to the elevated entrance, highlighting the inviting design and island charm.

4.94 out of 5 average rating, 63 reviews

2/2 SandDollars, CLUB, Boat Slip

“Sand Dollars”—a 2 bed, 2 bath beach house on North Captiva, a private island only accessible by boat. A quick 30 minute trip from Pine Island, North Captiva is a golf cart only island (that’s right, no cars!) that has the best beaches and shelling in the area. Sand Dollars is located one block in from the beach (200 steps). Sand Dollars has a Island Club membership with access to 2 swimming pools, paddle boards, kayaks. BYOB—bring your own boat and park at our boat slip (extra fee).

Superhost

Home in North Captiva Island

4.86 out of 5 average rating, 74 reviews

JUNE DISCOUNT*Golf Cart|Pool|Paddleboards|PingPong

We cover your Airbnb service fee! Welcome to Pirates Captiva, your private oasis! This spacious home sleeps 10 and features a heated pool with a poolside outdoor kitchen and grill. Explore the island with your complimentary golf cart, then relax surrounded by tropical beauty. get a game going on our volleyball court or explore on our paddleboards. Known for world-class fishing, beaches, and laid-back island living, this retreat is perfect for families seeking adventure and relaxation.

4.87 out of 5 average rating, 106 reviews

Cottage in Captiva

Cottage Secluded in Palms short walk to the Beach

Actual review left by a Guest “We had a great time in Captiva Island. It's the perfect place to get away for a relaxing, secluded, car-free vacation. Federico's cottage is conveniently located just a short walk to the beach and had all of the amenities we needed to relax and enjoy the trip. Federico was helpful and responsive when I had any questions. I highly recommend staying here if you are looking to disconnect and enjoy pristine beaches with lots wildlife and natural beauty. ”