Holiday rentals with a pool in Captiva

5 out of 5 average rating, 62 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, 24 reviews

Apartment in Sanibel

Sundial G406 - Brand New w/Beautiful Beach Views

On the beach with top floor ocean views! Enjoy sparkling ocean views from this relaxing coastal retreat, just steps from the beach. This large condo sleeps 4 and was fully renovated to include an expanded custom kitchen & luxury bathroom with large walk-in shower. Top of the line coastal furnishings in every room. The spacious master bedroom offers gulf views, king bed and a full-size desk if you need a quiet space to work. WiFi has been fully upgraded to make streaming and video a breeze.

5 out of 5 average rating, 80 reviews

Apartment in Sanibel

View of Gulf, Steps to Beach@The Turquoise Turtle

Welcome to The Turquoise Turtle, the newest and most stylish condo in Loggerhead Cay! Our personal vacation spot; this family friendly, coastal property overlooks the pool and is a two-minute walk to the gorgeous white sand beach. Fully renovated in 2021 with new kitchen, bathrooms, flooring, furniture, and curated beautiful beach decor. Grab a drink and relax on the patio, with a view of the beach and listen to the sound of the waves. At The Turquoise Turtle you will truly make memories!

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.

5 out of 5 average rating, 6 reviews

Home in Sanibel

Gulf House with pool and generator.

Beautiful single family house with an elevator and backup generator right across the beach. Large kitchen with morning nook and dinning area overlooks the beach. Tastefully decorated with designer furniture. Private backyard, backs to nature reserve. Covered all season pool with shower, gas grill and outdoor dining table. Beautiful landscaping! Close proximity to restaurants and all amenities. Enjoy with beautiful sunsets from front yard or take a stroll on the beach across the street.

5 out of 5 average rating, 11 reviews

Apartment in Sanibel

Sunny Sanibel - Gorgeous Walkout Unit

Loggerhead Cay 351 is a fantastic ground floor walk out condo residence in the sought after Loggerhead Cay development of Sanibel`s East End. "Sunny Sanibel" features two spacious bedrooms and bathrooms, a fully equipped kitchen, direct Gulf views, and a walk out patio, this residence is both beautiful and functional! With resort grade amenities including tennis, pickleball, Olympic sized heated swimming pool, shuffleboard, and community grills, guests will surely return year after year!

4.95 out of 5 average rating, 128 reviews

Steps To Private Beach Captiva Includes 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!!

4.9 out of 5 average rating, 121 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

4.94 out of 5 average rating, 104 reviews

Apartment in Captiva

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.

4.98 out of 5 average rating, 51 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.

4.95 out of 5 average rating, 39 reviews

Beachfront Island Retreat | 360 Views & Privacy!

Stella Maris is a beachfront family retreat on North Captiva with private beach access, panoramic Gulf views, and a 360° rooftop deck for sunrises, sunsets, and stargazing. Enjoy cathedral ceilings, a gourmet kitchen, formal dining with sunset views, and spacious living. All three bedrooms feature private en-suite baths. Relax in the hot tub, lounge outdoors, and explore the island with a private golf cart included during your stay.