Holiday rentals with a hot tub in St. James City

🌴ISLAND TIME! DOCK⚓️POOL🏊🏻‍♀️KAYAKS🛶Boat to Beach🏖 Pets

DIRECT GULF ACCESS HOME - Step back in time, recharge yourself on ISLAND TIME! Pine Island is laid back Old Florida where you can get away from it all. 4 beds, 2 baths. Steps to dock & canal. Sandy secluded Beaches are minutes away by BOAT! Island Hopping! Don't have a boat, no worries-water taxis & rentals are plentiful. Peaceful Outdoor Tropical Shower. Golf cart for rent at the house. Steps to private community pool & jet tub! Manual Bikes & Kayaks included. Sit back & relax! It's time 🐠🏝️

Outdoor spaces · Bathroom · Condition

The White Egret On Matlacha

Island home with direct access to Matlacha Pass. A 2-story property equipped with a pool and spa, high-speed internet, smart TV's, and smart home applications. Enjoy the balconies with sunrise and sunset views. Kayak directly off the back dock from the properties private kayak launch . You can fish right off the back dock, bike, or walk to the local shops/restaurants and the world famous Matlacha bridge, which is less than half a mile away. 2 Kayaks and 2 bicycles are included in the rental.

Hot tub · Outdoor spaces · Comfort

Island Sunset Retreat

Discover laid-back island living in this charming waterfront home. Located on a deep-water canal with direct access to the Intracoastal Waterway and Gulf of Mexico, this home offers the ultimate coastal lifestyle for boaters, anglers, and nature lovers alike. The kitchen is well equipped and has a family dining area. Enjoy your morning coffee on the deck and evenings in the jacuzzi. The home is close to local favorites, island dining, tiki bars, grocery stores, and outdoor activities.

Quiet · Hospitality · Accuracy

Calypso Shack, Fishing Paradise!

Calypso is a brand new spacious single level home. Canal-front getaway with a dock, which is key to access all the different adventures nearby, minutes from world class fishing, shelling and from top ranked beaches like Cayo Costa and North Captiva. Want to relax, kick back in the jacuzzi located in the screened lanai. It is the perfect getaway with either friends or family. Pine Island is filled with many convenient attractions, outdoor ventures and restaurants with entertainment.

Outdoor spaces · Family · Cleanliness

Coral Cottage hidden in Palms short walk to 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. ”

Hot tub · Outdoor spaces · Cleanliness

Beach Getaway + Golf Cart & Club Access

BOOKING FALL 2026 HOST PAYS AIRBNB FEE 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 proximity/ steps to the beach

Bathroom · Hot tub · Checkout

Waterfront Retreat, Sleeps 8, Resort Style Pool

🌴 In July a Lemonade – Your Perfect Island Escape in St. James City! Welcome to your perfect island escape in St. James City! This stylish waterfront home has everything you need for a relaxing and fun-filled stay. You’ll be just minutes from great local restaurants, local marinas, and right on the water for easy access to Pine Island Sound and beyond. Whether you’re boating, biking, or just lounging by the pool, this home is your ideal base for a laid-back Florida vacation.

Hot tub · Bathroom · View

Island Fun In The Sun! Water on 2 Sides

Water front, bring your boat! . Sit on tiki deck and watch the sunrise with your first cup of coffee or the dolphins. Kayak through the canal ways of Pine Island. Book a fun kayak,canoe tour or rent a golf cart or set up a fishing excursion. Buy all your fresh Catch of the Day at Island Crab Seafood Mkt. Or fish off of our dock out front. Ft Myer & Sanibel beach is hour drive away. No parties or pets. Dock & open water access out front. Adults only due to water front

Outdoor spaces · Bathroom · Cleanliness

Modern City Loft in Downtown River District

Welcome to Gun-Loft, a custom-designed modern sanctuary in the Downtown River District. This expansive 3500 square foot city loft is tailored for those seeking to embrace the cosmopolitan lifestyle, with the perfect blend of urban luxury and cultural richness. Whether it's a leisurely stroll to the Edison Ford Home, an exciting night out, or a culinary adventure in the restaurants nearby, Gun-Loft offers an unparalleled experience in the city's most coveted location.

Hot tub · Bathroom · Cleanliness

Tranquility Villa!!! ⚓️🛥🏝

Direct access to the golf waters out of St James City. Close to the 1000 islands, Captiva, Sanivel, Matlacha, etc. Bars, restaurants and night attractions on the island, 15 minutes to Matlacha.Perfect location to indulge yourself in a relaxing weekend paradise with a spacious house with 90" of water front dock sit back and enjoy the crossing of manatees, dolphins, and many of our Willelife species. Surprise yourself catching mangrove snapers, snooks,etc.

Bathroom · Hot tub · TV

Seaside Villa Destin In the heart of Pine Island

Our SEASIDE VILLA DESTIN is idyllically located on Pine Island off Cape Coral. Especially for boat lovers, the villa is therefore the perfect vacation home. The way to the Gulf of Mexico is not far and you can explore many beautiful islands around Pine Island and Cape Coral by boat. The boat dock may be used with pleasure. For further fun in the house there are kayaks, table tennis, table soccer and bicycles. Also for the little ones is provided.

Bathroom · Outdoor spaces · Comfort

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.

Outdoor spaces · Hot tub · Hospitality