Family-friendly holiday rentals in Naples

4.99 out of 5 average rating, 151 reviews

Pool House+Game Room, Moments to Beach & Downtown

Welcome to our Happy Place! This fully renovated Naples retreat sleeps 6 and blends modern comfort with family fun. Enjoy a bright open-plan living area, chef’s kitchen, and 3 bedrooms including a master with pool access. Step outside to your private screened oasis with heated pool, lounge seating, grill, canal and golf course views. The garage game room offers ping-pong foosball & arcade basketball. Just minutes to beaches, dining, and downtown, it’s the perfect getaway for relaxation and play.

An inviting heated pool is displayed within a retro-designed enclosure, featuring a striking patterned floor. Lounge chairs are positioned nearby, offering comfortable seating. Large screens protect against the elements while providing an unobstructed view of the surrounding greenery.

4.91 out of 5 average rating, 106 reviews

Luxury Design/Water-Heater-Pool/Pet friendly

Casa Vivir la Vida is a newly renovated home with luxury upgrades to ensure you with the most relaxing stay. - Heated Pool with Retro Design - 15 Min to Vanderbilt Beach area - 15 Min to Mercato Shops and Restaurants. - Designed for Families - Pet Friendly - Designe for up to 10 people, 3 bedrooms, 2 bathrooms, 5 beds and a futon - Free Parking - Laundry In Unit - Fully Equipped Kitchen - Huge Backyard with Gazebo. - Fast Wifi - Residential Neighborhood. - Barbecue Grill - 24/7 Available Hosts

A spacious private pool area features a heated pool and spa, enclosed by a screen for comfort. Lush greenery is visible through the arches, enhancing the serene setting. Modern lounge seating is positioned nearby, inviting relaxation and enjoyment.

4.97 out of 5 average rating, 110 reviews

Luxurious Naples Home. Heated Pool. Mins to Beach.

Have fun with the whole family at this stylish Naples Costal Paradise Home. Tropical Oasis within minutes to the beaches, restaurants, shopping, entertainment. Heated pool/spa no jets, Wi-Fi, big lanai with BBQ and more. House is a 3-bedroom, 2-bathrooms fully renovated in coastal contemporary style with tile floors, coastal art, big kitchen and more. King bed, queen bed, 2 full beds, big modular couch. House will comfortably sleep 6 adults plus children. It has all you need for great vacation.

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, 124 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.

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, 149 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!

The image showcases a bright, inviting pool area featuring clear blue water illuminated by string lights above, creating a relaxed atmosphere. Surrounding spaces include a cozy living room with comfortable seating and a spacious kitchen area with modern fixtures and finishes.

4.96 out of 5 average rating, 147 reviews

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Oasis Downtown Naples 3 BD/2 BA full house w/ a HEATED pool, outdoor entertaining, BBQ grill, lanai seating/dining for 8, outdoor games, 2 living rooms w/ large TVs (main room has a 75" screen TV), master suite w/ ensuite bathroom & flatscreen TV, all 3 bedrooms have king beds. Close to downtown restaurants/shopping (9 min), beaches/Naples Pier (14 min). DOG POLICY: Only after owner's approval, a non-shedding small dog is allowed with $100 per dog non-refundable fee (2 dog maximum).

A spacious and brightly colored outdoor living area features a screened-in pool surrounded by lush greenery. Comfortable seating and lounge chairs are set on a striped rug, creating an inviting atmosphere for relaxation. A ceiling fan provides additional comfort in this tranquil setting.

4.95 out of 5 average rating, 141 reviews

1 Mile to Beach! Pool, King Bed, BBQ, Games

Unleash your inner beach bum at this bursting-with-color vacation rental by Navigate Naples, just a 5-minute drive from the sugar-soft sands of Clam Pass Beach! This isn't your average beach house – enjoy morning coffee or happy hour cocktails on the covered patio, featuring a hand-painted wall mural by local artist. Our fully stocked home is the perfect place for you to make memories with family & friends. The central location, spacious layout, and comforts of home are sure to please!

The exterior of a two-story house is framed by palm trees, showcasing a welcoming entry with steps leading up to a spacious deck. Lush green foliage surrounds the home, providing a tropical feel beneath a clear blue sky.

4.86 out of 5 average rating, 148 reviews

#Closest2Beach - 3BD/3BA Oasis by RITZ BEACH GOLF

CLOSEST RENTAL HOME TO BEACH in Naples Park. Sleeps 6 with possibility of up to 10 by adding the additional Private Suites if available. Great Home for Large Family Vacations located near Ritz Carlton Beach Resort in Naples. Short Stroll to soft white sands at Vanderbilt Beach-Restaurants-Shops-Boats! See other listings for options: #Closest2Beach - 4BR/4BA Lux by RITZ- BEACH & GOLF #Closest2Beach - 4BR/4BA Cabana by RITZ BEACH GOLF #Closest2Beach - Huge 5BR/5.5BA by Ritz & Beach

The tropical lanai features a heated saltwater pool with a stone waterfall, surrounded by lush greenery and potted plants. A child safety gate provides restricted access. The area is designed with natural stone tiles and offers ample sunlight through the screen enclosure.

4.97 out of 5 average rating, 118 reviews

The Beach Getaway Home only steps from the water!

Perfect location for a beach getaway! Centrally located, enjoy all of Naples in the Naples Park neighborhood. Less than half a mile from Vanderbilt beach, walk or bike to the sunny gulf coast in under 10 minutes. Also steps away from the Ritz Carlton tiki bar! Shop groceries at the nearby Whole Foods, Trader Joes, and Publix. Feel like an evening out that's close by? Enjoy the Mercato shopping and dining area with several bars, restaurants, nightclubs, and even a movie theater.

A spacious driveway leads to a charming single-family home surrounded by lush greenery. Tall palm trees and vibrant landscaping frame the entrance, enhancing the serene ambiance of the retreat. The home is set back from the road, offering a private and tranquil atmosphere.

4.94 out of 5 average rating, 157 reviews

Venetian Photoshoot - La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

An outdoor kitchen and bar area is illuminated with soft lighting, showcasing a grill and ample counter space. The saltwater pool features calming purple lights, while seating stools are placed nearby, surrounded by lush tropical landscaping for a serene atmosphere.

4.98 out of 5 average rating, 122 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

The WaterSun Oasis is a 3 bedroom, 2 1/2 bath home, perfect for family or friends to get away. Less than one mile from Vanderbilt Beach, this high-quality private house, equipped with a top-notch outdoor pool area, is packed with best-in-class amenities to set your experience apart from others. Located just 30-minutes from RSW International Airport and surrounded by multiple beaches, restaurants, shopping centers, night life and more. Book your stay today!

4.99 out of 5 average rating, 143 reviews

Walk to The Ritz & Beaches, 2 Mstrs w Kings, Pets

Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...

Popular amenities for Naples family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.85 out of 5 average rating, 210 reviews

FULL Reno LARGE Beach House w/ Pool & Spa

5 out of 5 average rating, 10 reviews

Lovely Beach Cottage ~ 1 mile from Gulf w/Hot Tub

A spacious backyard is highlighted by a hot tub under a wooden gazebo. Sun loungers are arranged on the manicured lawn, while a sandy area offers relaxation. Greenery surrounds the space, providing a private atmosphere, with a putting green featuring a small flag for recreational activities.

4.94 out of 5 average rating, 344 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

Superhost

Flat in Naples

4.84 out of 5 average rating, 106 reviews

Oasis Naples Condo 2BR/2Bath

4.76 out of 5 average rating, 132 reviews

Beautifully private homeHeated Pool/Spa and Cabana

A serene saltwater pool is featured within a screen-enclosed lanai, surrounded by lush greenery and palm trees. A spa is integrated beside the pool, while comfortable seating and a shaded umbrella complete the outdoor space, inviting relaxation under the blue sky.

4.97 out of 5 average rating, 35 reviews

Heated Pool & Spa, Near Beach, Naples Luxury Home

A two-story house is presented with a light exterior and a tiled roof. The garage door features a modern design. Lush palm trees and greenery surround the driveway, which leads to the entrance. Natural sunlight casts shadows on the concrete surface.

4.94 out of 5 average rating, 129 reviews

Largest Home 1 mi from beach with saltwater pool

A serene outdoor space is showcased, featuring a saltwater pool and spa under a protective screen enclosure. The inviting turquoise water reflects sunlight, while tropical greenery is visible in the background, enhancing the tranquil atmosphere of the estate.

4.9 out of 5 average rating, 100 reviews

Serene acreage, Pool+Spa +3 King Bed Saltwater+Gym

Family- and pet-friendly home rentals

Superhost

Home in Fort Myers

5 out of 5 average rating, 3 reviews

Golf>Heated Pool • Sleeps 10 • Near Beach

4.99 out of 5 average rating, 110 reviews

A bright pool area features a sparkling blue swimming pool surrounded by beige stone tiles. Comfortable lounge chairs are positioned alongside the pool, with a shaded gazebo in the background. Lush greenery and palm trees create a serene atmosphere, enhancing the outdoor experience.

Bungalow in Naples Park

Sugar Beach Bungalow With a Pool!

4.97 out of 5 average rating, 37 reviews

Pool, Vanderbilt Beach, Mercato, Southern Exposure

5 out of 5 average rating, 15 reviews

Private Heated Pool• Outdoor TV• off season rates!

A serene outdoor space features a private saltwater pool with a spa, enclosed by a screened lanai. Soft lighting enhances the tranquil atmosphere, while lush greenery surrounds the area, creating a secluded retreat. Comfortable seating options are positioned nearby for relaxation.

5 out of 5 average rating, 51 reviews

Tropical Escape - Surf Chic Lux Salt Pool & Spa

An outdoor seating area features cozy lounge chairs and a fire pit, surrounded by gravel. Large glass doors in the background offer a view into the house, while the space is enhanced by green plants and a palm tree under a partly cloudy sky.

5 out of 5 average rating, 111 reviews

BEST Location Naples Park! Beach, Bikes, & Firepit

A screened lanai surrounds a heated in-ground pool with a curved edge. Comfortable lounge chairs and small tables are positioned nearby, while lush greenery and tropical plants decorate the perimeter, creating a serene and relaxing atmosphere.

4.91 out of 5 average rating, 11 reviews

Nestled in Naples | Lely Resort w/ Players Club

A heated pool is enclosed by a screened patio, providing a relaxing space for guests. Lounge chairs are positioned beside the pool, while the indoor dining area and living space can be seen in the background, framed by large glass doors that invite natural light.

4.92 out of 5 average rating, 254 reviews

Heated Salt Pool Retreat• Minutes to 5th ave Beach

Family-friendly home rentals with a pool

5 out of 5 average rating, 32 reviews

A vibrant pink inflatable flamingo floats on the clear water of the heated pool, surrounded by a screened enclosure. In the background, a shaded seating area with a large umbrella and wicker furniture is visible, framed by lush greenery and stone columns.

Home in Willoughby Acres

Blue Oasis!. The Perfect Getaway w/ Heated Pool!

4.97 out of 5 average rating, 31 reviews

Home in Bonita Springs

Family Oasis | Heated Pool + Beach Gear, Kid Ready

An inviting outdoor area features a heated pool surrounded by a screened enclosure. A floating pool toy is present in the water, while lounge chairs are positioned nearby. Sliding doors lead to the interior living space, enhancing the seamless indoor-outdoor connection.

4.96 out of 5 average rating, 27 reviews

Families-private heated pool & hot tub-pickle ball

4.83 out of 5 average rating, 23 reviews

Wonderful pool oasis in a great location 3BR/3BA

5 out of 5 average rating, 37 reviews

Lakefront Oasis with Heated Pool

A spacious outdoor area is highlighted by a uniquely shaped pool surrounded by lounge chairs. Umbrellas provide shade over seating areas, and a dining table is visible in the background. Lush palm trees frame the scene under a clear blue sky.

5 out of 5 average rating, 12 reviews

Resort Style Tropical Oasis

An outdoor dining area features a wooden table surrounded by six black wicker chairs, providing a comfortable space for meals. Adjacent, the screened-in pool showcases clear water, with lush greenery visible beyond. The ceiling fan enhances airflow, contributing to a pleasant environment.

5 out of 5 average rating, 45 reviews

Luxury home with heated pool

A spacious bedroom features a navy accent wall behind a white bed with striped linens. Adjacent, a modern bathroom is visible, showcasing a clean layout with white cabinetry. A well-equipped kitchen displays stainless steel appliances and a sleek island, while an inviting pool area is framed by a screened enclosure.