Holiday houses in Naples Bay

A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.

4.94 out of 5 average rating, 152 reviews

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

ValueFamilyCleanliness

5 out of 5 average rating, 29 reviews

Guesthouse in Naples

The Historic Coquina Cottages C- 2 Blocks to Beach

Cottage C is one of five quaint rental opportunities on a magnificently rebuilt Old Naples Cottage Estate c.1930. Two blocks from the Gulf of Mexico and within a two-minute walk of everything 5th Avenue and 3rd Street South have to offer. Cottage C is a charming, stand-alone studio-style cottage with a queen bed, a comfortable sitting area, and a full kitchen. The bathroom has been remodeled, and there is a private brick patio for outdoor seating. There is parking on the property for one car.

LocationFamilyBiking

5 out of 5 average rating, 18 reviews

Apartment in Naples

Lux Lakefront Resort | Beach 3 MIN Drive | 70"TVs

🌴Naples Coastal Escape🌴 “After several Airbnb visits this place definitely stands out among the rest…” Enjoy sunrises and sunsets in this remodeled, quiet, lavish lakefront oasis at Park Shore Resort. ☞Screened lanai w/lakeview+alfresco dining ☞Gourmet kitchen+Coffee bar+Wine fridge ☞Rainfall showerheads ☞Towel Warmer ☞Workspace desk ☞Cable TV TOP LOCATION ☀️ Clam Pass Beach->3min by car /~20min walk 🍹Mercato->9min car 💎 Old Naples/5th Ave->10min car 🛒 Fresh Market Grocery->10min walk

FamilyLocationBeach

A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.

4.96 out of 5 average rating, 128 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

FamilyLocationAmenities

A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.

4.94 out of 5 average rating, 154 reviews

Lux Oasis | 10 min Beach and 5th Ave•HTD Pool•Crib

Welcome to Your Naples Getaway! Why our home is perfect for your vacation: 🏖️ Beaches Nearby – Just a quick 10–15 minute drive to Via Miramar and Lowdermilk Beach. 📍Prime Location – Nestled on a peaceful street only 7 minutes from the iconic 5th Avenue. 🏡 Resort-Style Comfort – Relax in our fully screened lanai featuring: • Heated private pool • Luxury chaise loungers • Outdoor TV • Gas grill for BBQ nights Unwind with a cocktail, take a sunset dip, or simply kick back under the stars!

LocationValueLong stay

4.9 out of 5 average rating, 52 reviews

A modern living room is highlighted by a large wall-mounted TV above a wooden console table. A neutral-colored sofa is paired with a natural fiber rug and a wooden coffee table. A potted plant is positioned beside the sliding glass doors, allowing natural light to enter.

Townhouse in Naples

Villa Driftwood by Downtown & Beach

Welcome to your perfect Naples getaway! This beautifully renovated 2-bedroom, 2-bathroom townhouse blends modern comfort with laid-back Florida vibes. Located just 2.5 miles from shops & restaurants on 5th Ave. and less than 4 miles from Naples Beach—you’re in the heart of everything. Spend your days sunbathing, paddle boarding, or exploring nearby trails. In the evening, take a quick bike ride down to Celebration Park, where food trucks, live music, and waterfront drinks await.

FamilyLocationGetting around

5 out of 5 average rating, 27 reviews

Condo in Naples

Naples Luxurious Resort Retreat with Lazy River

Naples Tyme Retreat is an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining (see below for resort fees). Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.

LocationValueCleanliness

A spacious living area features a large sectional sofa in neutral tones, paired with accent pillows. A coffee table sits on a textured rug, while plants add a touch of greenery. Natural light floods in through expansive glass doors that open to a private outdoor space.

4.92 out of 5 average rating, 65 reviews

3 Bedroom Waterfront Getaway in Downtown Naples!

Your family will be close to everything when you stay at this centrally-located condo in Downtown Naples! Enjoy your morning Coffee out on your private deck overlooking the canal that takes your directly out to Naples Bay & the Gulf! Space to dock your boat as well. This 3 bedroom/3bathroom condo will transform your stay into a peaceful retreat, conveniently only minutes from 5th Avenue, the beach, & restaurants! What more can you ask for?!

LocationValueWalkability

Superhost

An aerial view showcases a private backyard with a sparkling swimming pool and a hot tub. A white umbrella provides shade over a lounged area, with comfortable seating options visible nearby. Lush green grass surrounds the pool area, enhancing the outdoor space.

4.88 out of 5 average rating, 42 reviews

Your Perfect Escape in the Heart of South Naples

Welcome to your dream getaway—just two miles from the world-renowned 5th Avenue and the pristine white-sand beaches of Naples. This stylish 3-bedroom pool home is the ideal blend of relaxed coastal living and upscale comfort. Whether you're seeking relaxation, adventure, or a little of both, this Naples retreat has everything you need for a truly unforgettable vacation.

FamilyLocationBackyard

4.92 out of 5 average rating, 25 reviews

Emerald Palm Villa, 2 bed / 2 bath with pool

Welcome to your dream getaway - short drive from the world-renowned 5th Avenue and the pristine white-sand beaches of Naples. This stylish 2-bedroom pool home is the ideal blend of relaxed coastal living and upscale comfort. Whether you're seeking relaxation, adventure, or a little of both, this Naples retreat has everything you need for a truly unforgettable vacation.

FamilyLocationComfort

A cozy living area features a light-colored sofa and a round, woven coffee table adorned with a small plant. Natural light filters through sheer curtains, highlighting a rattan chair positioned beside a tall mirror, creating an inviting and warm ambiance.

4.92 out of 5 average rating, 294 reviews

" The Bohemian Heaven " w/ SPA, 2miles to downtown

Welcome to the unique Bohemian Paradise. Completely renovated spectacular bright space, high-end furniture, a fantastic huge outdoor area, firepit, outdoor dining table, and BBQ station. Minutes away from restaurants and convenient stores, as well as historical Naples Pier, Naples beach, and 5th Ave/Downtown. You don't want to miss this experience.

FamilyLocationGetting around

A serene pool area is surrounded by lush greenery and palm trees, featuring a tiled patio that leads to the pool. Comfortable lounge chairs with colorful towels are positioned for relaxation. The outdoor space is complemented by a Tiki hut, adding charm and shade.