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!

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

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 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.

Gulf Access Canal, Kayaks, Bikes, Dock, Wildlife

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

Sunset Cove at Vanderbilt Beach

Welcome to your costal getaway in our one-bedroom condo, a 3-minute walk from Vanderbilt Beach. This fully equipped retreat features Wi-Fi, Smart TVs, a king-size bed, a pull out sofa bed for two, and an extra twin pullout. You are within a mile of Mercato offering shopping, dining, & dancing, and nightlife. Enjoy the blend of home comfort and beachside bliss in this ideal North Naples location, where every detail is catered to make your stay unforgettable.

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.

Luxe Coastal Getaway 4/3 Naples Vanderbilt Beach

This stunning single-story home is just one mile from the white sands of Vanderbilt Beach, perfect for an evening stroll or a quick bike ride. At Naples Coastal Vacations, we personally develop and manage our properties to ensure an exceptional guest experience. Every detail of this home has been thoughtfully crafted to offer luxury living that exceeds expectations, creating the ultimate coastal getaway.

Casa Bonita - Relax @ The Beach (Newly Remodeled)

Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.