Vacation rentals with a pool in Captiva

5 out of 5 average rating, 54 reviews

My Sea Shack~ 1 minute to beach, SH Club, G-Cart

Let "My Sea Shack" be your home away from home while you recharge your mind, body and soul on our island oasis, North Captiva! We are an unspoiled, low-key tropical paradise off the coast of Southwest Florida. This means that our beaches are uncrowded, and tourists and traffic are just a mainland memory! Leave your car and your cares at the marina because this island is only accessible by water taxi, boat or private aircraft. Each day, after exploring our paradise (by provided golf cart), let this spacious property welcome you back. Our new stilt home was built in 2018 and is ready to meet all your vacation needs! It features 2 bedrooms and a pull-out couch which will comfortably sleep 6. The master’s over-sized king bed will provide a nightly hug and a warm place to dream. Not tired quite yet...put on some tv and fall asleep while watching your favorite show on the flat screen. The 2nd bedroom can accommodate 3 people eaily with a comfy queen bed and twin. This room also has a flat screen making it a little easier for guests or little ones to doze off. In the morning, start your day off with your cup of coffee or tea on our sprawling deck. Relax and unwind in this comfortable home away from home! Spend your days on our beaches or stay as busy as you’d like with four on-island restaurants, two bars, kayak rentals, fishing charters, private chefs, cabana rentals, craft making opportunities, bicycle rentals, sunset cruises and our favorite - island hopping charters! My Sea Shack also comes with resort like amenities…take a dip in the community pool, play a game of tennis, enjoy priority seating at Safety Harbor’s restaurant -> On The Water or bring your private boat and have access to a boat slip (small daily fee applies). What makes this property TRULY SPECIAL though is the fact that it is only a 2-minute walk to Safety Harbor’s private beach entrance. This beach is so secluded, you will feel like you are on your own private beach. Choose your itinerary, let us take care of the rest~ your next adventure on North Captiva awaits. HOW TO GET TO THE ISLAND AND HOUSE Island Girl Charters has a ferry that runs from Pine Island to North Captiva. At the marina, you can leave your vehicle there. The boat crew will load up your luggage and groceries onto the ferry and you will be on your way..the actual ride is only about 20 minutes long. Many times you will see dolphins trailing behind as you make your way to the island. Upon arriving at the Safety Harbor drop off, our conceirge service will pick you up and load your belongings onto a trailer. If this is the first time, they will be happy to give you a quick tour before taking you to the house. The conceirge service will also take you back to Safety Harbor upon departure. INCLUDED~ Water osmosis system Wifi Netflix, disney +, hulu, amazon prime DVD player Blue-ray player 6 beach chairs Umbrella Beach towels Beach games Sand toys Pickle ball set Grill Propane tank Pack & play Highchair All spices Courant pizza maker (for frozen pizzas) Mixer Can opener Toaster Coffee maker Blender All kitchen cutlery Blowdryer T-fal cookware Vacuum Cleaning supplies Laundry det pods Hand soap Dish soap Toilet paper Paper towels 1 bottle of wine

5 out of 5 average rating, 11 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.

4.95 out of 5 average rating, 112 reviews

Welcome to Paradise at CollinsCoveCaptiva!

Welcome to your dream getaway in this beautifully updated, turnkey Key West-style home located in the heart of Captiva Island within walking distance to the village. Nestled in the charming Sunset Captiva community—lined with brick-paver streets—this home offers direct access to award-winning beaches and a private marina on the Bay. Boater’s Paradise? Immediate availability for the brand-new HOA-maintained boat docks. Or spend your days relaxing in the oversized, heated resort-style pool.

4.83 out of 5 average rating, 36 reviews

Apartment in Captiva

5136 Bayside Villas, Captiva Island

Welcome to a paradise! Our newly renovated Villa offers a spacious bedroom with a luxurious king bed and a separate living room with a pull-out sleeper sofa, accommodating up to 4 guests. The condo has hot water and is fully equipped. Bring your swimsuit! Enjoy the scenic bay views and watch dolphins and manatees from your window. Walk to the pristine beach and explore fine dining and shops just outside the resort gates. Laundry facilities are conveniently located on the ground level.

Guest favourite

4.95 out of 5 average rating, 121 reviews

Steps To Private Beach Captiva Retreat Golfcart

Relax and Reconnect at Our Charming North Captiva Island Cottage! Just steps away from the Gulf's pristine shores, this cozy retreat offers a private hot tub, perfect for families and beach enthusiasts. Enjoy modern amenities, a well-stocked pantry, and a complimentary golf cart to explore the island. Pet-friendly (with applicable fees), it’s easily accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach start making memories!!

Guest favourite

4.95 out of 5 average rating, 37 reviews

Beachfront Island Retreat | 360 Views & Privacy!

Stella Maris on North Captiva Island: a luxurious beachfront retreat with unparalleled privacy. This spacious 3-bedroom home with den and separate dining room offers unobstructed Gulf views from every level. Just steps to private beach access. Multi-level design culminates in a rooftop deck with breathtaking 360-degree views—perfect for sunrise and sunset. Features cathedral ceilings, gourmet kitchen, built-in hot tub, and includes a 6-seater golf cart for island exploration. Contact us!

5 out of 5 average rating, 46 reviews

Private Island Luxury * Pool * Dock * Club Access

🏠 Exquisite interior design & curated coastal furnishings 🏖️ Stroll to beach: chairs, umbrellas, wagon provided 🛥️ Shared boat dock - ask about availability. 🏊 Private pool 🍹 Screened-in pool bar 🏓 FUN! Ping pong, cornhole, PlayStation, bikes, games ✅ Fully stocked kitchen 🧴 Plush bedding, luxurious linens & bath amenities 💻 Starlink internet 🐶 Pet-friendly 🌴 Breathtaking views; luxury treehouse experience ⭐ Dedicated guest concierge to help you plan your perfect vacation

Guest favourite

Condo in Captiva

4.94 out of 5 average rating, 102 reviews

South Seas Resort Beach Villa 🌴 On The Beach !

South Seas 2527 is located in the Beach Villas area of the South Seas Resort, the Gulf of Mexico and pool can be viewed from the private lanai. This second floor unit has one king size bed located in the bedroom and pull out queen size sleeper sofa. The kitchen is fully stocked, there is an inside and outside dining table for your enjoyment. Beach chairs, umbrella and beach towels are provided with this unit since resort amenities are not available when you rent through an owner.

4.97 out of 5 average rating, 58 reviews

Cottage in Captiva

The FlipFlopper Beach House - North Captiva Island

FlipFlopper Beach House - well appointed family focused beach home only a 3 minutes walk from the White Sand Beaches on the Gulf of Mexico and 3 min walk to Island Club Amenities on North Captiva Island. Rate includes Luggage Deliver, use of Golf Cart and Members Access to The Island Club. Hard limit on 6 guests - rare exceptions but please ask - infants are not counted in the above 6 person limit! Private Hot Tub on the rear deck amongst the Sable Palms.

4.98 out of 5 average rating, 48 reviews

Home in Sanibel

Coastal Chic Island Escape

Just 150 yards from Sanibel's peaceful beach, our home offers unmatched luxury: direct beach access, a heated saltwater pool, private pickleball/tennis court, and sea-view dining. A king suite, additional king bedroom, playful bunk room, and separate apartment provide comfort for all. Perfect for those seeking a serene escape, our home is not suited for loud gatherings or parties. Please help us preserve the tranquility of this special place. 28-day minimum.

5 out of 5 average rating, 12 reviews

Condo in Captiva

South Sea Serenity II Coastal Luxury Beach Condo

⚓️Welcome to South Seas Serenity II! This newest and most stylish condo in South Seas! The remodeled modern luxury condo is nestled in heart of Captiva, one of the premier vacation destinations in the Southwest Florida. There are AIRBNB properties and there are South Seas Serenity Properties. We set ourselves apart by creating a 5 Star luxury experience while still having the space and quaintness of a AIRBNB property.⚓️