Beach house holiday rentals in Old Naples

Updated 2BR Barefoot Pelican – Bay Views & Pool

Enjoy waterfront living in this beautifully updated 2-bedroom, 2-bathroom condo on the second floor of Barefoot Pelican in North Naples. Set along Vanderbilt Lagoon, this residence offers a peaceful setting with sweeping water views while being just minutes from the beach, dining, and shopping. Inside, the condo features an open and airy layout with stylish updates throughout. The kitchen is equipped with modern appliances and sleek finishes, while both bathrooms have been tastefully remodeled. A private screened lanai overlooks the lagoon — the perfect spot to start your day with coffee or unwind at sunset. The Barefoot Pelican community offers amenities that make everyday living feel like vacation, including a heated pool and spa right on the water, barbecue areas, and available boat docks for rent. Covered parking and elevator access add to the convenience. Located just a short walk to Vanderbilt Beach, the Ritz-Carlton, and Mercato’s shops and restaurants, this condo places you in the heart of North Naples’ best lifestyle. Whether you’re here seasonally or year-round, this property delivers comfort, views, and an unbeatable location.

Location · Cleanliness · Beach

Stylish Retreat, Walk to Beach, Pool, 2 King Beds

Welcome to Aquarelle Beach House (ABH), built in 2019 & located on the 500 block of Naples Park! ABH is furnished in modern, coastal style, the perfect space to enjoy your beach vacation & everything Naples has to offer: →Short 1.3 mile walk/ride to beach →Private, heated, well-lit pool →High end furnishings, Artist Designed →Stocked kitchen with beverage/wine fridge →Dine poolside in the covered back patio →Minutes from dining, shopping, and supermarkets! Click the ❤ to add to wishlist!

Location · Family · Access

Private Waterfront Paradise 3/3 Pool Home on Canal

This tropical paradise waterfront 2-story pool home is well-equipped with all the essentials needed for an amazing Florida getaway. Gather in the serene, private back yard where an expansive heated pool awaits you. Watch dolphins swim by the dock as you lounge and sunbathe. Enjoy free use of the many kayaks, paddleboards and bikes (for kids and adults). Perfectly located close to restaurants and multiple white-sand beaches, this North Naples retreat has everything you have been looking for.

Location · Value · Cleanliness

New! Beachside cottage style cutie-host pays fees

Welcome to Sandy Cay!! Located just steps to the beach and walking distance to Times Square, Sandy Cay is a cute, beachy green colored two-story cottage style home with 4 bedrooms, 4 1/2 baths. Each bedroom has a private ensuite bathroom. Open concept living and fully equipped kitchen with induction cooktop, oven, microwave, dishwasher. Breakfast nook/dining area has shiplap covered walls and seating for up to 8. This home offers all the charm of an iconic beach cottage ... on stilts!

Location · Family · Comfort

Tivoli Paradise Salt Pool & Spa Villa with a Water

Step into the comfort of this luxurious 4BR 3Bath waterfront pool villa in Naples, FL. Situated in a tranquil, family-friendly neighborhood of Briarwood, it promises a serene retreat, close to golf & country clubs, restaurants, and numerous attractions. ✔ 4 Comfy BRs (3 BR w King beds! 1 BR w two TWIN XL Beds) ✔ Salt Spa and Pool ✔ Lake view ✔ Bicycles ✔ High-Speed Wi-Fi PETS REQUIRE APPROVAL PRIOR TO BOOKING ($300/small dog). Pool heat $25/night June 1-Sept 30, $35/night Nov 1-May 31

Location · Value · Check-in

Bayfront Cottage, Steps to Beach

Welcome to Seashell Hideaway, a charming coastal retreat perfectly positioned on Hickory Boulevard. This bright and cozy 2-bedroom, 2-bath cottage offers the best of both worlds—set directly on the bay with a private dock, yet just across the street from Bonita Beach. Spend your days spotting dolphins and manatees, soaking in colorful sunsets, or walking to the beach for sun and surf. Whether relaxing on the patio or exploring nature, every moment here feels like a seaside treasure.

Location · Accuracy · Kitchen

FMB Farmhouse

Relax at this new, 3 bedroom home. 3 minute walk or bike ride to the beach or restaurants. Large Master bedroom with king bed and en suite bathroom. Second bedroom has a queen bed and shared guest bath. Third bedroom has two sets of bunk beds. Amenities include Wi-Fi, flat screens in living and bedrooms, heated pool, hot tub, grill and AC. 3 bedrooms, a stocked kitchen, washer/dryer, outdoor dining and a cozy living room make this property perfect for families, couples or friends.

Value · Location · Cleanliness

The Turtle Nest

Welcome to "The Turtle Nest." You cannot rent a closer property in Naples Park to the beach. It is a 7 minute walk to the beach! This is a 2 story new construction 4 bedroom, 3 bathroom, 2 half bathroom, pool with spa home ready for a beach lovers ultimate vacation. Perfect rental for a multi-generational family vacation. The Mercato and Pavillion shopping centers are within walking distance where you can rent bicycles, get ice cream, watch a movie, and eat at a restaurant.

Family · Location · Bathroom

Tommy Bahama House | 3-Bedroom Beachfront Retreat

The one and only Tommy Bahama House, bedrooms and three bathrooms, located directly on Bonita Beach in Bonita Springs, Florida. The elegance and beauty of Tommy Bahama House is apparent when you turn off Hickory Blvd. onto the paver driveway and see the ginger bread trim and lattice garage door's. You will immediately know why you choose to spend your vacation or Holiday on this beach front treasure. Look no more for that perfect beach front private home!

Location · Value · Beach

Lagoon Breeze Beach House

Lagoon Breeze Beach House is a bright, updated 4-bedroom, 3-bath home just a 5 to 7 minute walk from the sand on the quiet south end of Fort Myers Beach. Sleeping up to 9, it's made for families and groups. Spend your days at the beach with the included chairs, umbrella and cooler, then come home to your private heated pool and hot tub, grill dinner on the patio and unwind with smart TVs and fast Wi-Fi. Bikes are provided for easy rides around the island.

Family · Location · Outdoor spaces

Luxury Heated Pool • Walk to Beach • Cabana Oasis

Top 1% of homes in Naples on Airbnb. If location and relaxation are at the top of your list, welcome to your dream stay in Naples! This newly renovated 3-bedroom, 2-bath coastal-modern home features a new heated pool, spacious outdoor cabana, and the perfect location — just a few minutes’ walk (less than a mile!) to one of Florida’s most beautiful beaches. Top 1% of homes This home is one of the highest-ranked based on ratings, reviews, and reliability.

Value · Family · Cleanliness

Grace by The Sea · 2025 Build · Steps to Beach

This stylish coastal home offers a brand-new experience with a spacious lanai and backyard, all with just a 6-minute walk to the sugar sand beach. Start your morning with coffee on the covered front porch, enjoying Gulf breezes. Relax by the pool with a book throw something on the blackstone grill, play corn hole or enjoy cozy outdoor seating for lounging and dining. End the day with a sunset stroll or a short drive to nearby bars and restaurants.

Location · Family · Kitchen