Waterfront vacation rentals in Old Naples

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

Lazy River, 4 Pools, 5th Ave Resort Personal Oasis

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

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

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.

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a perfectly located 1 bedroom condo in the heart of Old Naples, just a 1/2 block from vibrant 5th Avenue with its restaurants, boutiques, and cafés, and only four short blocks to the beach. Set in a charming Old Florida building surrounded by multi-million-dollar estates, the condo offers access to a heated pool perfect for a refreshing dip after a day at the beach. Inside, you’ll enjoy fast WiFi with a dedicated workspace, and the convenience of keyless, contactless entry.

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.

Beaches & 5th Ave 2.5 miles away!

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.

Tree Top Retreat!Private, close to 5th Ave & Beach

Looking for privacy and a place that’s super close to 5th Ave? You found it!! Stay high up in the trees in your very own 2nd story studio overlooking the beautiful pool & yard! Very spacious, clean & comfortable w/ pull out couch & new king bed & mattress! You’re close to the action but tucked away in your own private setting. We’re a 5-8 minute car ride/Uber or 10-15 minute bike ride to 5th Ave! *PLEASE NOTE: The pool, patio & front yard will not be able to be used by guests*

25%OFF·Beach3mi·2HtdPools·Tennis·PickleBall·Bikes

✨ Introducing Catch of Naples ✨ 🎾 Stay active at Blue Coral Naples Coastal Home in WTC – with 16 tennis & 4 pickleball courts, 2 pools, hot tub & sauna right in the community! 🏖️ Just 3 miles to Naples beaches & 10 min to downtown dining. 🚲 Bikes, beach chairs & umbrellas included for endless outdoor fun. 🌴 Relax on the lanai while kids play safely in our gated community. 🌐 Guests recognize us as Catch of Naples — read the reviews and see why active travelers choose us!

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.