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.

4.97 out of 5 average rating, 108 reviews

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.

Home in Palm River

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 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, 134 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.

4.97 out of 5 average rating, 117 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, 145 reviews

LUXE Oasis | 10 min Beach+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, 143 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).

5 out of 5 average rating, 105 reviews

A heated pool is enclosed within a screened lanai, featuring a colorful beach ball floating on the water's surface. Sunlight filters through the mesh walls, illuminating the pool area and surrounding greenery, while lounge chairs are positioned nearby for relaxation.

Cottage in Naples Park

Beach House on pond w/ HEATED pool - sleeps 6

This secluded and beautiful beachside getaway is yours. Perfectly positioned easy access to white-sand beaches & fabulous shopping/dining/golfing/site seeing experiences of Naples. (2 bed 2 bath.) Gorgeous lakeview, (turtles/ducks incl.). HEATED POOL. Enjoy fresh coffee at sunrise from lanai watching swans take their morning swim or have a nightcap near shimmering moonlit pond. We warmly welcome you to rest, relax and stretch-out at this incredibly charming Beach*House cottage.

4.99 out of 5 average rating, 177 reviews

A spacious stilt home features large windows that provide ample natural light. An outdoor deck with seating overlooks the canal, surrounded by palm trees. A boat dock is visible alongside smooth stone pathways leading to the house, creating a tranquil waterside setting.

Home in Wiggins Bay

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

4.89 out of 5 average rating, 100 reviews

A clear blue pool is surrounded by lounge chairs and umbrellas, framed by lush palm trees and tropical plants. The serene atmosphere invites relaxation, with a paved terrace providing access to the pool area.

Villa in Naples Park

835 GulfShore Villa | Mins 2 Mercato & White Sands

Welcome to 835 GulfShoreVilla! Bask in the Florida sunshine, practice your golf swing, & explore the Gulf Coast in style when you choose this completely remodeled vacation rental! This 2BD/1.5BA Villa is just a block away from Mercato Shopping Center, where you'll unique shops, eateries, live entertainment & more. With a fully equipped kitchen, 2 Smart TVs, free WiFi, modern decor, & a peaceful location, this home invites you to kick back, relax, & enjoy!

4.96 out of 5 average rating, 99 reviews

Beach! Heated Pool, Game Room, 2 Kings, 2 Suites

We are Super Hosts since 2018. You can see our history of reviews by navigating to my profile. The perfect home for a beach vacation just 3 minutes to the beach and 2 king beds. Every room in the house includes streaming TV even the outdoor lanai. A large chef's kitchen with an oversized island is great for entertaining. Bikes, towels, beach chairs, and toys are all included! Great house to enjoy the Florida sun.

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.

4.98 out of 5 average rating, 130 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.

5 out of 5 average rating, 6 reviews

Home in Park Shore

Pink Palm Paradise-Pool/Hot Tub- Near to beach

Beautifully updated 2 BR home just west of 41, minutes to the beach. Enjoy true Florida living with a large saltwater pool, sun lounges, and a soothing saltwater hot tub. Bright, modern spaces inside with comfortable furnishings throughout. Private outdoor area for relaxing or dining. Close to Naples beaches, dining, and shopping. *MONTHLY DISCOUNTED RATES AVAILABLE*

Popular amenities for Naples family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.97 out of 5 average rating, 119 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

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, 342 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

A living area features a comfortable grey sofa adorned with decorative pillows, complemented by a dark accent chair. A modern coffee table sits centrally, with light streaming in from a nearby window. The space is enhanced by elegant artwork and fans overhead.

4.94 out of 5 average rating, 142 reviews

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

4.95 out of 5 average rating, 146 reviews

* Endless Summer * Close to Beach with private Spa

Superhost

4.76 out of 5 average rating, 131 reviews

Beautifully private homeHeated Pool/Spa and Cabana

A private outdoor space features a saltwater pool and hot tub, surrounded by lush greenery. Comfortable seating arrangements include a fire pit and outdoor dining area, all sheltered under a screened enclosure, providing a tranquil setting for relaxation.

4.97 out of 5 average rating, 212 reviews

LUXE: Beach Home w/ Screened Pool & Spa, BBQ

4.86 out of 5 average rating, 21 reviews

A spacious pool area is highlighted by a newly installed heated pool with a sun shelf and a separate spa. The surrounding screened enclosure provides protection from insects while allowing natural light and fresh air, creating a bright and inviting outdoor space.

Home in Palm River

Edition | Family Stay, Pool,Spa, BBQ, Near Beach

A light-filled living room features a comfortable seating arrangement with soft sofas and an armchair, complemented by a decorative area rug. Large windows invite views of lush greenery, while a painting enhances the tranquil atmosphere. A ceiling fan is mounted for added comfort.

4.98 out of 5 average rating, 311 reviews

Garden House-2 Bedroom/2 Bath-Naples / Park Shore

Family- and pet-friendly home rentals

The spacious outdoor area features a screened saltwater pool with an integrated hot tub, surrounded by tiled decking. Lounge chairs provide seating for relaxation, while a serene view of the landscape is visible through the screen, allowing for enjoyment of the outdoors.

4.92 out of 5 average rating, 24 reviews

Sun-kissed Naples Paradise

5 out of 5 average rating, 14 reviews

A serene outdoor space is showcased, featuring a spa and pool area surrounded by palm trees. The sun casts a warm glow over the water, while a canal is visible in the background, lined with boats and lush greenery.

Home in Vanderbilt Beach

Tropical Oasis! 1 Mile to Beach! Heated Pool & Spa

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, 146 reviews

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

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, 28 reviews

Pool Home Minutes to the Beach

Superhost

Home in Bonita Springs

5 out of 5 average rating, 3 reviews

Belle Rio Paradise - Pool Home near beach on canal

An open-concept living area features a spacious sectional sofa with decorative cushions. A dining table with elegant chairs is visible, along with a modern kitchen displaying dark cabinetry, stainless steel appliances, and a large island with bar seating. Ceiling fans and recessed lighting enhance the ambiance.

4.93 out of 5 average rating, 91 reviews

Naples Home-Min to beach,shops,dining. Heated Pool

5 out of 5 average rating, 24 reviews

A charming turquoise home is surrounded by lush landscaping featuring palm trees and colorful flowers. In the foreground, a heated swimming pool is nestled within a paved area, accompanied by several lounge chairs positioned for relaxation and sunbathing.

Home in Sun Terrace

Walk To Beach & Shops! New 4 Bdr Pool Heated

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, 248 reviews

Heated Pool Retreat• Naples Oasis Minutes to Beach

Family-friendly home rentals with a pool

A serene outdoor space features a saltwater pool surrounded by tropical plants and trees. Two chairs are positioned by a fire pit table, each with a drink resting on it. A stone wall encloses the area, enhancing the tranquil setting.

4.9 out of 5 average rating, 59 reviews

Sea Turtle Heaven

5 out of 5 average rating, 64 reviews

A screened-in outdoor space features a sparkling pool surrounded by stone pavers. Comfortable seating arrangements are visible nearby, along with a dining area under a stylish roof. Lush greenery provides a natural backdrop, enhancing the relaxing atmosphere of the backyard.

Home in Willoughby Acres

NEW+Modern.Heated Pool.Minutes to beach.Sleeps 10+

Superhost

A spacious living area features a large sectional sofa with a dark ottoman at its center. Light-colored tile flooring and neutral wall tones are complemented by decorative wall art. A dining area with a wooden table is visible, along with access to the outdoor space through sliding doors.

4.73 out of 5 average rating, 26 reviews

Modern 4- bedroom house just 1 mile from beach

4.83 out of 5 average rating, 23 reviews

A serene outdoor area features a large swimming pool surrounded by palm trees and sun loungers. The backdrop showcases a two-story home with ample glass windows, allowing natural light to illuminate the interior. Soft colors in the sky hint at sunset.

Villa in Naples Park

Luxurious "Villa in the Hills"

The serene backyard features a heated in-ground pool surrounded by lush landscaping and a hot tub. A screened patio offers a dining table and lounge area with inviting cushions. The open concept kitchen and living space are visible, showcasing modern appliances and ample seating for relaxation.

4.97 out of 5 average rating, 97 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

5 out of 5 average rating, 6 reviews

The outdoor space features a heated pool illuminated in soft blue, with a hot tub adjacent to it. Expansive screened-in areas showcase comfortable seating and a dining arrangement, providing a cozy ambiance under the evening sky. Warm light spills from the indoor living area.

Home in Lely Resort

King Sleep # Bed Lely Resort, Golf + Grand Piano

A heated pool area features relaxing lounge chairs partially submerged in the water, accompanied by a large white umbrella providing shade. The pool is surrounded by a spacious deck, framed by lush greenery and palm trees, with additional seating visible in the background.

4.98 out of 5 average rating, 106 reviews

Private Naples Oasis w/ Cart, Gym & Saltwater Pool

A covered patio area features a cozy seating arrangement with a dark sofa and a wooden dining table. A modern fire pit is situated at the center, complementing the views of a screened-in pool and surrounding greenery beyond the transparent enclosure.