Family-friendly vacation rentals in Old Naples

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.

4.95 out of 5 average rating, 118 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

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, 107 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.

The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.

4.98 out of 5 average rating, 118 reviews

FUN AT THE BEACH

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier( to be rebuilt)and 3rd Ave Famous Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king mattress and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refridgerator.

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.

4.95 out of 5 average rating, 135 reviews

LUXE Oasis | 10 min Beach • HTD Pool+5th Ave •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!

4.91 out of 5 average rating, 163 reviews

Downtown Condo at Naples Pier Beach

Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

5 out of 5 average rating, 171 reviews

Guesthouse in Lake Park

By the Beach and 5th - Studio Apartment with Pool

Great location! Newly renovated! A studio guest apartment with your own private entrance, full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining & shops, the mall, the zoo, beautiful Baker Park, and that's not all- Only steps away are local restaurants and shops! Bikes and beach equipment included! Did we mention there's also a pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth speaker? This home is 325 square feet of clean cuteness!

4.98 out of 5 average rating, 182 reviews

A bright living area features large glass sliding doors that open to a private patio with views of lush greenery. A round dining table with four chairs is positioned adjacent to the doors, while a dark sofa is placed nearby, creating a welcoming and open atmosphere.

Cottage in Naples

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.

4.93 out of 5 average rating, 131 reviews

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

A spacious living area showcases a blue leather sectional couch and a marble-topped coffee table. Bright white bar stools are positioned around a light-colored kitchen island, with navy blue cabinets in the background. Natural light enters through nearby windows, enhancing the inviting environment.

4.95 out of 5 average rating, 151 reviews

Three Palms Oasis - 2 Miles to Beach and 5th Ave

We invite you to stay at this stylish, yet affordable luxury home with a gourmet kitchen right in the heart of central Naples. Three Palms Oasis is located in a quiet coastal neighborhood under two miles from the best that downtown Naples has to offer including the sugar white sand beaches, Naples Design District, dining and shopping on 5th Ave, Naples Zoo, Olde Naples, and so much more! You won’t find a better value in the prestigious 34102.

An inviting outdoor space features a heated pool and spa, enclosed by a fine mesh screen. Comfortable seating areas are arranged nearby, complemented by lush greenery. Sunlight streams through the enclosure, highlighting the tranquil atmosphere of this private oasis.

4.92 out of 5 average rating, 115 reviews

Private Oasis in the ♥ of Naples ☀Heated Pool/Spa☀

Escape to The Private Oasis in the heart of Naples! → Welcome to 2,279 square feet of modern and elegant furnishings → Minutes to 5th Avenue, Tin City, Beach, Zoo, and Pier → Fully equipped kitchen fit for the chef at heart → Dine and unwind poolside in the enclosed lanai → Take a dip in the heated pool and spa → Grill masters will love the outdoor kitchen & bluetooth speakers → Click the ❤ to add listing to wishlist!

4.8 out of 5 average rating, 332 reviews

Guesthouse in Old Naples

Waterfront Sea Cottage

Enjoy Naples in this private waterfront tiny cottage conveniently located on the Gordon River with gulf access near the heart of Downtown 5th Avenue. Our cottage is only 1.5 miles (2.4 km) from the beach and is located within walking distance to parks, shopping, bars, restaurants, and many outdoor activities. Located in a safe, vibrant, and transitioning community full of life and the true flavor of old Naples.

An inviting collage showcases various areas of the Naples Holiday House. Bright outdoor seating is paired with an umbrella, while the living space features comfortable seating and coastal decor. A cozy dining area invites meals al fresco, and serene beach views complete the relaxing atmosphere.

4.96 out of 5 average rating, 201 reviews

4BR Near Downtown Naples | Kings Bikes. Beach Gear

Relax in this spacious 4-bedroom Naples home just minutes from the beach, 5th Ave shopping, and downtown dining. Perfect for families and groups, this 1,864 sq ft retreat features 2 king beds, bikes, beach gear for 8, outdoor games, BBQ, and two outdoor lounge areas everything you need for a stress-free Southwest Florida getaway. We have stellar reviews, come check us out & see for yourself.

Popular amenities for Old Naples family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.93 out of 5 average rating, 162 reviews

A resort-style pool is surrounded by tropical palm trees, with waterfalls cascading from built-in rocky features. The clubhouse is visible in the background, featuring light-colored siding and large windows. Lounge chairs are scattered around the pool area, inviting relaxation.

Condo in Naples

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

A charming exterior view of the property features a welcoming entrance with a vibrant blue door. Lush green hedges and palm trees frame the landscape, accented by colorful tropical plants in the flower beds. A smoothly paved driveway leads to a covered parking area.

5 out of 5 average rating, 18 reviews

*SwimSpa* Tiki Bar, Fire Pit, 1.5 mile to Beach

4.94 out of 5 average rating, 109 reviews

An open concept living space features stylish wooden flooring with ample natural light. A comfortable sofa and armchair are arranged around a wooden coffee table, complemented by a spacious dining table. A modern kitchen area is visible in the background, equipped with contemporary appliances.

Guest suite in Naples

Main-Stay is a luxury 2/1 central to all Naples.

4.97 out of 5 average rating, 216 reviews

A clear blue pool features a spa area, bordered by decorative stone. Two lounge chairs are positioned alongside the water, offering a relaxing area. A dining table with multiple chairs is visible in the background, with a privacy fence and lush greenery completing the serene outdoor setting.

Home in Naples Park

Last Minute Deals! Walk to beach! Jacuzzi & Pool

4.91 out of 5 average rating, 46 reviews

A hot tub is situated beneath a wooden pergola, surrounded by softly glowing string lights. Clear glasses and a bottle sit nearby, reflecting the warm ambiance. Palm trees can be seen in the background, adding a tropical touch to the evening setting.

Villa in Old Naples

4.93 out of 5 average rating, 138 reviews

A serene beach scene features soft, white sand leading to gentle waves. A long wooden pier extends into the calm water, framed by a vibrant sunset sky filled with hues of orange and purple. The atmosphere conveys tranquility as clouds float overhead.

Home in Naples Park

Beach Bliss Haven|Steps to Vanderbilt| Free HotTub

4.98 out of 5 average rating, 144 reviews

A serene pool area features a champagne-style hot tub connected to a shimmering pool, surrounded by a marble deck. A vibrant mural of a sea turtle decorates the wall, while lounge chairs are positioned nearby, inviting relaxation amidst lush tropical landscaping.

Home in Bonita Springs

Luxe Unique: Close to Beach, Hot Tub, Heated Pool

4.99 out of 5 average rating, 152 reviews

Vacation home in Naples

75"TV, World Tennis Club, Beach 4ml, Sauna, HotTub

Family- and pet-friendly home rentals

A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.

4.96 out of 5 average rating, 171 reviews

Tropical Cottage by the Sea- your own private home

A heated pool is surrounded by lush greenery and a fenced yard. Six lounge chairs are arranged around the pool area, each with a colorful pool float nearby. Two umbrellas provide shade, enhancing the space for relaxation and enjoyment.

4.9 out of 5 average rating, 106 reviews

The Periwinkle, a heated pool home 10 min to beach

4.77 out of 5 average rating, 157 reviews

A cozy living area is presented, featuring a sectional sofa in a neutral tone and a round wooden coffee table. A wall-mounted television sits above a simple white fireplace. Natural light enters through a window, with a decorative mirror reflecting the space.

Apartment in Naples

Bayshore Getaway

4.91 out of 5 average rating, 142 reviews

An Egret named Eddie

4.91 out of 5 average rating, 131 reviews

Guest suite in Naples

Newly Renovated Studio 5 Min From Beach

5 out of 5 average rating, 18 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

4.83 out of 5 average rating, 183 reviews

The kitchen features modern white cabinetry and sleek countertops with a subtle grey pattern. Appliances include a refrigerator, microwave, and oven. Under-cabinet lighting enhances the space, while glass pendant lights provide illumination above the bar area with seating for two.

Guest suite in Naples

Charming cottage bay area

4.97 out of 5 average rating, 32 reviews

A cozy living area features a dark sofa paired with a round table holding a floral arrangement. A television mounted on the wall displays calming imagery. Natural light enters through a window adorned with bamboo shades, creating a relaxed ambiance.

Cottage in Naples

Cozy Cove

Family-friendly home rentals with a pool

A refreshing swimming pool features floating inflatable items, including a unicorn and colorful loungers. Water fountains gently spray into the pool, surrounded by a spacious deck. Lush greenery and a privacy hedge create a serene environment, while inviting lounge chairs are positioned nearby for relaxation.

4.89 out of 5 average rating, 83 reviews

Tropical Pool Paradise close to 5th Ave/Beaches

4.99 out of 5 average rating, 145 reviews

Pool House+Game Room, Moments to Beach & Downtown

4.94 out of 5 average rating, 119 reviews

The outdoor living space features a light-colored wooden deck surrounded by lush greenery. A cozy seating arrangement with white chairs and a central table invites relaxation. A shaded area integrates an outdoor kitchen and BBQ station, enhancing the alfresco dining experience.

Guesthouse in Naples

Dolphin Bungalow in Naples

A modern kitchen features white cabinetry and a spacious island with white quartz countertops. Stainless steel appliances, including a microwave and oven, are visible. A television displaying a beach scene adds a touch of relaxation, while natural light fills the open layout.

5 out of 5 average rating, 34 reviews

Luxurious condo steps to beach with heated pool!

An aerial view captures the condo complex positioned near the Gulf of Mexico. The scene features the peaceful sea, sandy beach, and palm trees, with a glimpse of the community pool nestled within the property.

5 out of 5 average rating, 11 reviews

Old Naples Beach Condo

Guest suite in Old Naples

A serene pool area is framed by elegant columns and surrounded by lush greenery. The light yellow exterior of the building complements the turquoise water, which reflects the blue sky. Steps lead from the pool to the entrance, enhancing the inviting atmosphere.

4.9 out of 5 average rating, 118 reviews

Southern Charmer, a handsome beach studio (Naples)

An expansive lanai features a shimmering pool with a waterfall-edge spa and in-pool loungers. The outdoor space is surrounded by a screened enclosure, providing views of well-kept greenery. A comfortable seating area and dining space are visible in the background, enhancing the outdoor living experience.

5 out of 5 average rating, 24 reviews

Pool Home Minutes to the Beach

An open-concept living space features a light-colored sofa with patterned cushions, surrounded by rattan chairs. A modern kitchen with white cabinetry is visible in the background. A large wall-mounted TV displays a serene seascape, enhancing the airy atmosphere with natural light from nearby windows.