Vacation rentals in Pine Island Sound

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.

LUX Villa w/ Private Salt Water Pool, Lanai, Canal

Are you looking to swim, relax outdoors, fish and take in beautiful sunsets on a wide gulf access canal? If so you will fall in love with this stunning newly constructed custom built home! The 2750 square foot home is bright & airy with two main bedroom on-suites & a separate family wing! The gourmet kitchen, dining room & great room open via large sliders to the lanai & pool w/ views of the canal in much desired SW Cape! Beach inspired villa! Large captains walk & Tiki! Check out our 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!

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa510 is a newly built waterfront retreat ideal for extended stays in Cape Coral. Enjoy peaceful salt canal water views and manatees from the lanai, then relax in your private heated pool and spa—perfect year-round. The outdoor kitchen and lanai create an easy, comfortable daily routine. Inside offers three private en-suite bedrooms, a den with optional airbed, open living space, and TVs in every room. Close to shopping, dining, and beaches—perfect for snowbirds seeking comfort and ease.

Panoramic Ocean Views, Sleeps 10, Heated Pool

🧭 The Compass Rose | Beachfront Getaway 🌴 Steps from the island’s widest, most beautiful beach with panoramic Gulf views, a private heated pool, 2 golf carts, and 4 kayaks! Enjoy 4 king beds, 5 decks, a gourmet kitchen, ping pong, foosball, and more. Located 50 yards from the only public Gulf beach access with golf cart parking. Explore North Captiva Island - Florida’s secret island paradise, accessible only by boat. Sleeps 10. Pet-friendly (case-by-case). No parties.

​Boater’s Paradise: No-Bridge Gulf Access & Pool

⚓ Direct Gulf Access (No Bridges): Cruise to open water! 🏊‍♂️ FREE Heated Pool: Waterfront views, zero daily heating fees. 🛏️ Group Oasis: 4BR | 3BA | 7 Beds (Sleeps 13 comfortably). 🎣 Outdoor Living: Fish from your dock, BBQ & spectacular sunsets! 🐾 Pets Welcome & Fast Wi-Fi! 🚙 Massive Parking: Room for boat trailers! 📍 Location: Heart of Matlacha, minutes to Cape Coral. ⚡ Prime season dates book fast. Lock in your direct water access and reserve your dates today.

Villa Sunset Serenade II

Completely renovated and newly furnished! Experience the most beautiful weeks in the brand new Villa Sunset Serenade II, completely renovated by a professional design team. The open living room equipped with a great lighting concept with the brand new large modern kitchen of the dining and cooking island as well as a fireplace and large TV. The large Italian leather couch with the large electric armchair allows a great view of the wide canal and invites you to enjoy.

Charming 2-BR Home w/ AC, Dock & Peaceful.

Discover this charming 2-bedroom waterfront home in peaceful Saint James City. Each bedroom features a comfortable queen bed, plus a cozy living room with a sofa bed for extra guests. With 2 full bathrooms, everyone enjoys space and privacy. The home offers air conditioning and heating for year-round comfort. Relax indoors, unwind by the water, or plan your next island adventure from this inviting home away from home. We’re always happy to share local recommendations.

Bountiful Bokeelia

Swimming pond closed until November. Tropical fruit season Summer. Mangoes everywhere! Snowbirds welcome, availability Winter 2027. Forget your worries in this spacious and serene oasis. Professionally decorated, Coastal Chic, extremely quiet, 3 acre fenced and gated property off the beaten path on Pine Island. So close yet so far away! The immediate mainland has all that you could possibly need. The property boasts a unique natural swimming pond. Pet paradise!

2 Bedroom Island Oasis Getaway

Hi to all of our past & future guests. Our home is such a great place to stay, we are just steps from the water, fishing & the beautiful sunsets. We have space for your boat or you can rent one locally. Completely remodeled home as of March 2022, there is a master bedroom and a 2nd bedroom along with a large bathroom. Guest will have access to the entire house including the lanai, patio, boat dock, boat ramp and parking.

Salt Life Serenity

Canal front property, pet friendly, complete with pool, jacuzzi, and boat dock. 2 King beds with 2 full bathrooms. Den/tv room that pulls out into a comfortable Queen bed. We pride ourselves on having a fully stocked kitchen with multiple coffee makers to make your stay in this newly renovated home one to remember. Enjoy fishing from the dock or watching the manatees as they move with the tides.

New Home! Heated Pool · Outdoor Bar · 2 Golf Carts

🏝️ Brand-new 2026 luxury home on North Captiva Island 🏊 Large private pool 🍹 Covered outdoor bar + grill 🛺 2 golf carts included 🎮 Game zone: ping pong, cornhole, darts & more 🚴 2 fat-tire beach cruisers included 🏖️ Beach chairs, umbrella & cart included 👑 King suite w/ soaking tub + 2 queen guest rooms 🍽️ Designer chef's kitchen 🌴 Large private lot — car-free island paradise