Holiday rentals with a pool in Captiva

Ocean View+Pickleball & Pool+5 Min Walk to Beach!

❤We have OVER EIGHTY 5★ Reviews......Book with Confidence❤ ★ 2 Story, 2,115 Sq Ft Home w/ 2 Patios ★ Views of the Ocean on 2 sides ★ 5 Min Walk to Nearly Private Beach ★ Sleeps 8 - (2 Kings, 2 Twins, Sofa Bed) - 3 Bathrooms ★Fast Wifi, Keurig, & Smart TVs ★ Access to Pool, Hot Tub & Pickleball ★ Pack N Play + Board Games ★ Experienced Hosts - (easy check-in, clear communication, recommendations, clean home) You deserve to see some legendary Captiva Sunrises & Sunsets at least once in your life!

" 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.

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!

Steps to Beach Captiva Includes CLUB & Golfcart

HOST PAYS AIRBNB FEE WINTER SPECIALS Golf Cart and Club amenities Included 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(small fee) accessible by ferry, boat, or plane. With beach gear, access to the club pool, and unbeatable proximity to the beach STAY WITH US

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).

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.

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.

Waterfront - Bayside Villas Captiva

LOCATION, LOCATION, LOCATION! The 180 degree views from our screened in lanai are amazing! You get full views of the Bayside Marina, Pine Island Sound and the pool deck! This condo was recently renovated in June of 2025. Our place is privately owned so you still get access to the resort's beautiful public beach which is within walking distance across the road thru the Beach Villas path, the Bayside Villas pool and hot tub! We also provide beach chairs, an umbrella and a beach wagon!

Heated Pool, Golf Cart, Pickleball& Close to Beach

🍹 Outdoor Oasis: Pool, Bar, Games, TV & Shower 🐚 Beach Access: A Short Leisurely Stroll Away 🛥️ Shared boat dock - ask about availability. 🎾Access to club with tennis, pickleball. 🏠 Chic Mid-Century Surf Aesthetic 🛌🏽 Supreme Rest: Westin Heavenly Beds ✅ Gourmet Chef’s Kitchen 🏖️ Premium Beach Essentials: Chairs & Umbrellas 🐶 Pet-Friendly 🧻 Full Amenities: Luxury Toiletries & Supplies 💻 High-Speed Internet 😊 Dedicated 24/7 Local Host Support for a Perfect Stay!

Captiva Sweet Retreat at Bayside Villas

Captiva Paradise. Privately owned premier corner location one-bedroom, two bath Bayside Villa with beautiful lanai view of the marina and pool. Step outside for a Short walk to the fabulous beach and village of Captiva. Enjoy mesmerizing sunsets, beach walks and large pool. Open floor plan with spacious living, dining area, large waterfront lanai, kitchen with breakfast island and roomy bedroom with ensuite bathroom. See other things to note for resort access info.

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.

Waterfront 2BR Condo (Fully Updated!) w/ 2 Bikes!

This unit has been updated, including an extended kitchen, granite counter tops, impact windows and doors, ceramic tile and a full bath along with a second half bath. This corner unit allows for outstanding canal views and privacy. Tennis and heated pool are just downstairs. Two bicycles are available. Please note that small construction projects are still taking place on the grounds outside due to Hurricane Ian. Enjoy!