Holiday rentals with a hot tub in St. James City

Manatee Lookout-Boat to Beach, Dock, Pool, Kayaks

Welcome to Manatee Lookout Cottages- Our cute cottage is a brand NEW BUILD! Direct Gulf Access right in our backyard - private dock, Old Florida Vibes, peaceful natural environment, wildlife & manatee watching. Gorgeous beaches a short boat ride away.The best fishing! Made a Mini beach for you to enjoy. Soothing outdoor tropical shower! Free kayaks & manual bikes, amazing private community pool & jet spa steps from the home. Golf cart available for extra fee. All about relaxation here! 🏝️🐬🦩

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.

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.

Waterfront Oasis with Boat Lift & Hot Tub

Bask in endless sun at our Jugg Creek canal-front home, a stone's throw from Charlotte Harbor and iconic islands like Captiva and Boca Grande. Dive into 'Old Florida' with unspoiled beaches and cute eateries. Watch dolphins from your doorstep and savor rainbow sunsets. Our beautiful cottage boasts a outdoor hot tub and shower, screened in porch, grill, and kayaks with a kayak launch right on the dock. Docking is on us, with a new dock & 10k pound boat lift available April-December.

Experience of a lifetime

Get ready for the experience of a lifetime at this hidden gem! As you walk through the front door you will begin your journey into the best vacation of a lifetime. Keep on going through the sliders & that will lead you to the incredible resort style pool that will leave you in awe!!! Here you are in the heart of it all. Shopping-dining-entertainment is all within a 5 minute drive. The beautiful beaches just 7 miles away. If you enjoy boating & relaxing this is the place for you.

Last Minute Offers Beach + Golf Cart + Club

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

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.

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

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.

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.

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.

Relaxing 4-Bedroom Waterfront Home with Hot Tub

Your family will be close to everything when you stay at this centrally-located place. Featuring 3 bedrooms and two baths upstairs and an efficiency apartment with 1 bedroom / 1 bath and livingroom downstairs. It is located in one of the best subdivisions close to all the restaurants. There is a new hot tub on the upper deck overlooking the water.