Waterfront holiday rentals in Old Naples

Upstairs - 2 Blocks From Everything

This is one of five quaint rental opportunities on a magnificently restored Old Naples Cottage Estate c. 1910. Located two blocks from the Gulf of Mexico & Naples Pier and within walking distance of everything 5th Avenue and 3rd Street have to offer. The private entrance to the stairs brings you to a newly renovated, magical spot. Comfortable seating arrangement, full kitchen with marble counters forming a sitting bar, all new equipment, two king bedrooms, and a full bathroom off the kitchen.

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.

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.

Naples Cottage for two- your own private home

Welcome to your own, private waterfront home close to restaurants, coffee shops, parks and Naples beaches! This perfect tropical cottage for two comes with a stunning view of a natural lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens, Pickle Ball courts or shops near by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do near you!

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.

Beach House on pond w/ HEATED pool - sleeps 6

This secluded and beautiful beachside getaway is yours. Perfectly positioned easy access to white-sand beaches & fabulous shopping/dining/golfing/site seeing experiences of Naples. (2 bed 2 bath.) Gorgeous lakeview, (turtles/ducks incl.). HEATED POOL. Enjoy fresh coffee at sunrise from lanai watching swans take their morning swim or have a nightcap near shimmering moonlit pond. We warmly welcome you to rest, relax and stretch-out at this incredibly charming Beach*House cottage.

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.

"The Boho Bliss" Lakeview Elegance 3miles Downtown

Discover Bohemian Bliss in this uniquely styled home, 2mins walk to Sudgen Lake in Naples that includes beach, lake activities, walking trails or biking. Vibrant energy with the comfort of your creatively adorned space that tells you a story. All brand new, high-quality furniture, Tempur-Pedic mattress, Very Fast WiFi, King-size bed, TVs in all bedrooms, fully equipped kitchen, Fire pit, BBQ. Reserve now so we can welcome you home, to a boho-inspired sanctuary in the heart of Naples.

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.