Waterfront holiday rentals in Old Naples

Chic resort, 4 pools, walk to 5th Ave Restaurants!

Welcome to Naples finest gated downtown resort, rewarding guests with a measure of privacy and serenity. The resort features an amenity rich environment with marina, waterfront dining and shopping, Euro-style spa, an expansive activity center, three crystal-blue resort pools, multiple hot tubs, meandering lazy river and a complete fitness center. Walk to downtown 5th ave or take the complimentary shuttle to beaches or 5th Ave HAVE A LARGER GROUP? - ASK ABOUT ADDING ANOTHER UNIT TO YOUR BOOKING

Waterfront Hideaway

This picturesque Airbnb is a hidden gem nestled along a canal, one minute boat ride to the Caloosahatchee River. The living room, bathed in natural light is perfect for taking in the scenic views. The spacious bedroom has a king-size bed, ensuring a night of blissful rest. The full kitchen is equipped with all modern appliances. Close to Sanibel & Fort Myers Beach. Bring your boat & dock it on the seawall, ready to set sail whenever your heart desires. Book now - your coastal paradise awaits!

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

Lely Greenlinks Golf Resort Luxury Condo

This beautiful and spacious 2-bedroom, 2 bath condo is luxurious, impeccably clean, well-stocked - and perfect for your next vacation getaway! Greenlinks Golf Resort is situated within the prestigious Lely Resort Golf & Country Club in Naples. It is just a two minute walk over to the clubhouse where you can tee off on the Lely Flamingo or Mustang golf courses. Ideal central location between downtown Naples and Marco Island, you are just 15 minutes from downtown or beaches in either location.

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

Tropical Cottage by the Sea- your own private home

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

Little Gem By the Beach and 5th w/Patio Old Naples

JUST A SHORT WALK TO THE BEACH AND 5th AVE, IN THE HEART OF OLD NAPLES, WITH A RARE, PRIVATE PATIO! Totally renovated in January 2023! A beautiful, one-bedroom, one-bath home, with only a 5-minute stroll to the beach and dining! Just outside the living room is a private, landscaped patio overlooking a pretty lake, which is an unusual and lovely feature of this home! Inside, you'll enjoy a fully-equipped kitchen with granite countertops, a comfortable king bed, and washer/dryer in the condo.

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

5th Ave & Beaches 10 Minutes Away! 2 BD/2 BA

Bring your family and friends to our Southwest Florida paradise! This stylish space is the newest addition to our profile. Located in Naples Florida and within a 7 min drive to 5th Ave shops, restaurants, and beaches. Enjoy a 10 min walk to Celebration Park and local restaurants. Guests can enjoy this newly remodeled condo that has everything you will need for your Naples getaway. **If you have a larger party, inquire and view our profile about the 3 other condos on this property.

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.

2br/2ba spacious House near the Ocean

Welcome to our stylish and comfortable retreat, located just 1.3 miles from the sandy shores of Vanderbilt Beach and the scenic beauty of Wiggins Pass State Park. With the vibrant Mercato district nearby, you'll have access to an array of dining, shopping, and entertainment options. Our well-appointed accommodations include two bedrooms with king-sized beds, as well as a queen-sized sleeper sofa, making it perfect for families or groups of friends.