Waterfront holiday rentals in North Naples

505 Sunset Key Estate | Luxury Courtyard Pool Home

Welcome to 505 Sunset Key Estate | Luxury Courtyard Pool Home Located on the coveted Vanderbilt Drive, this 5BD, two-story, heated pool home features Old Naples Charm w/ a North Naples location. Enjoy breathtaking sunsets from the private balcony or take a short stroll to world class, white sand beaches. Professionally designed to give you a sophisticated vacation home away from home. The upmost attention was paid to selecting quality furnishings that are as functional as they are beautiful!

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!

Private pool-spa home just blocks from the beach

Hello, owners Ted & Maya welcome you to an amazing private pool & spa home surrounded by a luscious backyard plant garden just 2 blocks from the beach. Fully remodeled 3 bedrooms, plus a den, 2 baths with lanai complete with a private pool and spa, 2 car garage and offered turnkey furnished! Simply and elegantly decorated spacious home. As you enter, there is a den with a couch, massage chair, TV on the wall, and a desk area perfect for working from home with high-speed WIFI internet service.

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!

Tropical Oasis! 1 Mile to Beach! Heated Pool & Spa

Your dreams will become a reality when you stay at this gorgeous, recently updated 4-bedroom, 3-bath, canal-front home in the exclusive Conners at the Vanderbilt neighborhood and boating community in the heart of Naples. Enjoy canal access to the Gulf of Mexico, the shimmering sands of Vanderbilt Beach at your doorstep, and the Ritz Carlton, La Playa Beach and Golf Resort, and the idyllic Delnor-Wiggins State Park just minutes away. Pet cleaning fee-$250 each (2 dogs - 50 pounds or under)

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.

Entire home -Charming Canal Cottage in Bonita

Our charming canal cottage is located in a peaceful neighborhood with gulf-access. ONLY a 5-minute bike ride to Barefoot beach & Vanderbilt beach. A short walk to over a dozen local restaurants! Prime location West of US-41, close to casual & fine dining & easy access to RSW Airport, the Promenade, Mercato & Waterside Shops. This home is renovated with a modern open-concept living space with a screened lanai. This home has a doc and is 15 minute access to the gulf with no bridges.

Beautiful 3 BR Waterside Condo w/ Private Terrace

Regatta at Vanderbilt Beach is a luxury waterfront condo, just 1 & a half block from Vanderbilt Beach& Ritz Carlton. The unit is over 2000 square foot, beautifully decorated & offers a very large private terrace overlooking the bay. Private rear stairs to boat dock & parking garage. A short walk to Vanderbilt Beach where you can enjoy white gulf beaches & sunsets. Private gated resort style complex w/ both family friendly pool, an adults only lap pool, spa, grilling area & gym

Cozy 1BR 1BA Beach Retreat in Sunny Naples, APT 2

Welcome to your peaceful Naples escape! This charming 1-bedroom, 1-bath canal-front unit in a quiet four-plex offers a serene retreat with tranquil water views. Enjoy the convenience of on-site laundry, ample parking, and a comfortable, thoughtfully furnished space perfect for relaxing after a day of exploring. Ideal for couples, solo travelers, or business guests looking for a quiet, well-located stay just minutes from beaches, dining, and everything Naples has to offer.

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.