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 Top Floor 2 Bed 2 Bath Sleeps 6

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!

Oceanfront Views + Balcony Sunsets Bikes Included

“Caihlin, you were a phenomenal host.” – Sandy, May 2025 ☀️ What You’ll Love: • Unbeatable Views: Floor-to-ceiling glass sliders open to the Gulf—watch dolphins, sunsets, and seabirds from your private balcony. • Free Beach Bikes: Cruise the beach or explore nearby Lovers Key with the 2 bikes we provide. • Updated Interior: Modern kitchen, stainless appliances, granite countertops, and a cozy living area with coastal decor. • Comfy King Bed: Sleep to the sound of waves in a plush king-size

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.

Stunning Views from Above at Vanderbilt Beach

Enjoy sunrises over Vanderbilt Bay and sunsets over the Gulf of Mexico in this 8th floor corner-unit. Wraparound windows providing excellent panoramic views. The split-bedroom floor plan includes two bedrooms and two baths, a kitchen, a living room, a dining room, and two separate balconies — one with views to the east overlooking the bay, and another expansive wraparound balcony with views overlooking the Gulf of Mexico. Electric shutters throughout provide ease and maximum storm protection.

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.

New(2024)Waterfront/Gulf access, Oasis

Brand new, modern canal-front oasis with direct Gulf access & Hot tub. Stunning two-bedroom, en-suite home offers the perfect retreat, enjoy sunsets from the deck & sunrises from your private balcony or bedroom. Located minutes from charming downtown Bonita Springs & a short 15-minute drive to Naples' vibrant Mercato district, you're also just 10 minutes from the pristine sands of Barefoot Beach. Experience the best of Florida's coast with style & comfort in this serene waterfront escape.

Walk to Beach~Hot Tub~Game Room~Bikes

Step into a sun-soaked oasis! Walk, bike, or drive less than a mile to tranquil Vanderbilt Beach or 1 mile to lively Mercato's dining, shopping, and entertainment scene. This spacious newly renovated home offers a blend of modern comfort and coastal elegance. Prepare meals in the fully equipped kitchen or relax in the hot tub in the screened-in lanai. Whether you're lounging inside or basking on the beach, it's the perfect seaside sanctuary for your next getaway!

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.