Family-friendly holiday rentals in Naples

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, 135 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 serene outdoor space is featured, with a heated saltwater pool flowing gently into a stone-accented area. Comfortable seating is arranged beneath a large umbrella, providing shade. Two pool floats rest on the water, surrounded by lush greenery and a clean white fence.

5.0 out of 5 average rating, 114 reviews

Luxury Beach Home | Private Pool

Welcome to this whole home, beach-themed oasis featuring a secluded outdoor living space including a covered lanai with TV, heated saltwater pool, hot tub, sun deck with chaise lounges, and outdoor living room seating with a large canopy umbrella. Just blocks from Vanderbilt Beach, Delnor-Wiggins, and the expansive shopping and dining available at the Mercato. This 3-bedroom, 2-bath home comfortably sleeps 8 and has all amenities needed to create an unforgettable stay for your group or family.

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, 159 reviews

Lux Oasis | HTD Pool•10 min Beach and 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!

A spacious living area is highlighted by a light-colored sofa adorned with turquoise cushions. An elegant chandelier hangs from the ceiling, complementing the large wall-mounted TV. Natural light fills the room through windows, with a dining area visible in the background.

4.97 out of 5 average rating, 104 reviews

Beach, Sun and Fun! *Beach House * New Listing

Location! Location! Location! 3 beautiful bedrooms, 2 baths, just 1 mile to the beach and entertainment. Peaceful and private, this home boasts an abundance of room for entertaining and outdoor space, free parking and access to private beach. Conveniently located close to the Venetian Village, Water Side mall and 5th Avenue which futures several casual and upscale dinning, shopping and multiple entertainment venues. Great for a relaxing vacation and enjoying the Florida sunshine and sunsets!

4.96 out of 5 average rating, 139 reviews

Beach, Hot Tub & htd pool. 2 Owner Suites w 2 King

The perfect Naples beach getaway for families and/or groups of 8–10 and just a few minute bike ride to the beach. The home doesn't just sleep large groups, it supports it with every space designed for guests to gather. Bikes and beach gear are included, plus guest-only perks including local beach know-how, golf cart rental and shuttle options, pre-arrival fridge stocking, Naples recommendations, and special benefits with select local partners. Less time planning. More time enjoying Naples.

4.97 out of 5 average rating, 115 reviews

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

🏡 THIS LUXURY PROPERTY IS IDEAL FOR FAMILIES/SMALL GROUPS (SLEEPS 8) YOU HAVE MADE IT! You are now viewing one of the most unique properties in Naples 🌴 & here is why: 🌳 This property is on 2.5 acres of land & VERY private 🏖️ Beach is only 12 minutes away 🍽️ 10 minutes from heart of the city (Dining, shopping, nightlife) 🏊‍♂️ Heated saltwater pool/spa ⛳ Golf putting green 🎾 2 Pickleball Courts 🏓 Ping Pong table W/AC in garage 🏀 Adjustable Basketball Hoop 💻⚡ Blazing fast WIFI

5.0 out of 5 average rating, 135 reviews

Your Private NaplesBeach Getaway

🌴 Private Oasis 3 mins from The Beach 🌊 Welcome to our slice of paradise in Naples Park, Florida! Nestled 3 minutes away from the pristine sands of Naples Beach, world-famous Mercato Shops & Dining, and Publix/Walmart. Only 15 minute north of 5th Ave Downtown District. Our renovated home features a privately fenced backyard with new heated saltwater pool, a custom miniature golf zone, and many outdoor games for every guest 😃 Simply the perfect cozy retreat for your beach getaway⛱️

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.

4.95 out of 5 average rating, 125 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.

4.93 out of 5 average rating, 167 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.

A private heated pool is surrounded by lounge chairs and umbrellas, set against a vibrant sunset sky. Lush landscaping frames the area, enhancing the secluded feel. A shaded outdoor bar area is visible in the background, inviting relaxation and social gatherings.

4.88 out of 5 average rating, 126 reviews

Outdoor Kitchen | Heated Pool Near Beach + 5th Ave

Your oasis awaits! Beyond the doors of this impeccably renovated home you'll find a private, heated pool with a fantastic, fenced-in, backyard with mango trees, tropical vegetation & string lights. Beach towels, gear, and loungers are provided so all you need is your suit! Work remotely from the office areas and grill out each evening (propane grill provided). Need space for a crowd? We have multiple homes within walking distance available for large groups.

4.98 out of 5 average rating, 111 reviews

Home in Bonita Beach

Luxury Home, Steps to the Sand! Pet Friendly!

Breathtaking sunsets await from the second story wrap-around deck on this gorgeous coastal style newly built home located steps from Bonita Beach and the famous Doc's Beach House! This home features a premier location and luxury stay all in one. Walk just steps to the beach, rent a boat, paddleboard, jet ski, cabana or beach loungers just across the street at Docs or enjoy an incredible meal at one of the areas great local restaurants just mins from the door!

An outdoor living space features a screened lanai overlooking a pool. Comfortable loungers are positioned around the pool. A dining table with multiple chairs is set under a ceiling fan, complemented by a large area rug. The scene is bathed in natural light.

4.99 out of 5 average rating, 141 reviews

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.

Popular amenities for Naples family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 159 reviews

Boaters Bayshore Bungalow w/HOT TUB view of water.

4.78 out of 5 average rating, 146 reviews

Beautifully private homeHeated Pool/Spa and Cabana

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.

4.88 out of 5 average rating, 114 reviews

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

5.0 out of 5 average rating, 103 reviews

" Velvet Bloom” Bubbling Spa Retreat with Sauna

Luxe

A serene outdoor area features two lounge chairs positioned beside a clear, inviting pool. A small table adds convenience between the chairs. Lush greenery surrounds the pool area, offering privacy, while the sky above is bright with a few scattered clouds.

4.95 out of 5 average rating, 105 reviews

Naples Luxury Orange Blossom Oasis 4/3 Tiki Bar

4.99 out of 5 average rating, 168 reviews

Holiday home in Naples

World Tennis Club | Pools, Hot Tub, Beach 4 Miles

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.

4.91 out of 5 average rating, 138 reviews

Private Oasis in the of Naples Heated Pool/Spa

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.

4.96 out of 5 average rating, 253 reviews

Last Minute Deals! Walk to beach! Jacuzzi & Pool

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 124 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!

4.96 out of 5 average rating, 101 reviews

Luxury Private Retreat with New Pool in Naples

4.87 out of 5 average rating, 156 reviews

The screened patio area features a solar-heated pool surrounded by lush greenery. Comfortable lounge chairs are positioned alongside, and a gas BBQ grill is visible nearby. Floating pool toys and colorful cushions add a relaxed touch to the inviting atmosphere.

Bungalow in Naples Park

Little Treasure House minutes from Beach & Mercato

4.95 out of 5 average rating, 158 reviews

Beachside Haven | Family 3BR Near Vanderbilt Beach

4.92 out of 5 average rating, 110 reviews

Tropical Oasis! 1 Mile to beach Heated Sltwtr Pool

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, 155 reviews

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

4.93 out of 5 average rating, 105 reviews

Naples Luxury 5BDRM Home/Htd Pool/SuperClean/Pets

4.89 out of 5 average rating, 334 reviews

A private heated swimming pool is set within a screened area, featuring a clear blue surface reflecting the surrounding greenery. A gentle incline leads to the shallow end of the pool, while a silver railing provides support for access.

Villa in Naples Park

Del Mar Villa

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 137 reviews

Lush greenery surrounds a walkway leading to the entrance of a two-story building. Tall trees and trimmed hedges create a natural border. The sunlight casts playful shadows on the ground, highlighting the tropical landscape that envelops the property.

Apartment in Old Naples

Perfectly located Old Naples condo

An outdoor dining area features a table with teal accents and an umbrella, set near a glistening pool. Lounge chairs are positioned along the poolside, while a gazebo is visible in the background, surrounded by greenery and a white fence.

4.98 out of 5 average rating, 155 reviews

Cozy Vacation Home * Heated Pool*Near The Beach !

4.93 out of 5 average rating, 101 reviews

A bright and airy living area features a comfortable sofa paired with decorative pillows. A glass coffee table rests atop tiled flooring, while a dining table is positioned nearby. A flat-screen TV is mounted on the wall, and wall art adds a coastal touch.

Apartment in Old Naples

Luxury 2-Bedroom. Steps to Naples Beach & Town.

5.0 out of 5 average rating, 23 reviews

Home in Golden Gate

Relaxing Naples Getaway–Comfort, Style & Sunshine

Luxe

5.0 out of 5 average rating, 7 reviews

Pickleball, Pool, Hot Tub, Game room-Naples escape

5.0 out of 5 average rating, 23 reviews

Home in Golden Gate

White Palm Paradise

4.95 out of 5 average rating, 40 reviews

Emerald Palm Villa, 2 bed / 2 bath with pool