Family-friendly vacation rentals in 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.

4.95 out of 5 average rating, 198 reviews

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

A bright living area is furnished with modern white sofas and a dark armchair. Large glass doors lead to the pool area, allowing natural light to fill the room. Vibrant textiles and a ceiling fan enhance the relaxed ambiance of the space.

4.98 out of 5 average rating, 103 reviews

Backyard Oasis - Large heated pool/Wi-fi/Lanai/PS3

Enjoy a great vacation in our beautiful Naples home. With three spacious bedrooms, modern decor, plentiful natural light, and a full kitchen, this upscale home is perfect for groups of friends or families seeking a sunny getaway. Enjoy direct access to a private pool and an ideal location in a safe neighborhood just a short drive from stunning beaches. 8 Min Drive to 3rd Avenue 10 Min Drive to Naples Botanical Garden 12 Min Drive to Naples Pier and Beach Experience Naples With Us & Learn More

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, 100 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, 116 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, 133 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!

4.97 out of 5 average rating, 186 reviews

A single-level traditional home is showcased with a bright green garage door and welcoming front entrance. The circular driveway is paved, surrounded by neatly manicured grass. Mature trees and shrubs are positioned around the property, providing a touch of greenery under a clear blue sky.

Home in Lake Park

Relaxing Naples Home close to beach and downtown.

Enjoy this single level "just renovated" traditional Naples home, just blocks from beautiful beaches, the Naples Zoo, Naples Preserve, the Conservancy of Southwest Florida, the Gordon River Greenway Park, Coastland Mall, and 5th Avenue's abundant restaurants and shopping. Features include 3 bedrooms (including 1 bedroom with bunk beds (double and twin), a 2 car garage, covered lanai and laundry. It is located in the Lake Park neighborhood known for its quiet charm and mature canopy trees.

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, 129 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 light-filled living area features a spacious beige sofa and a comfortable lounge chair. A coffee table sits in front, with decorative items placed on it. A dining table for four is visible, accompanied by abstract wall art and soft lighting from ceiling fans.

4.98 out of 5 average rating, 111 reviews

Cozy 1 Bedroom Villa - Beautiful Naples, Florida!

Perfect One Bedroom Villa only 2.5 miles from the beach and 2 miles from beautiful 5th Ave in Naples! This Villa is perfect for those coming to Naples on Vacation, for work, or seasonally! It has everything you need to live comfortably for a short or long period of time including a 200 sq foot private front porch. Enjoy everything Naples has to offer within a short drive! This unit is perfect for 1-2 guests. It can fit up to 3 with a pullout couch in the living room.

A spacious outdoor area features a rectangular pool surrounded by lounge chairs. A covered seating area is visible to the left, with a shaded structure supported by wooden beams. Lush greenery and palm trees add a tropical ambiance, complementing the exterior of the home.

4.92 out of 5 average rating, 108 reviews

Private Heated Pool | Playset | Near the Beach!

Just minutes from the beach, Flamingo Feliz is a cheerful 3-bedroom getaway with a brand-new pool, cozy tiki lounge, and family-friendly extras. Enjoy smart TVs in every room, a fully stocked kitchen, beach gear, bikes, and plenty of space to relax. The heated pool (heating avail. Oct–May) and outdoor living areas make it perfect for a sunny Florida escape. Located near 5th Ave dining, shops, and Naples' best beaches—everything you need for a laid-back vacation!

4.81 out of 5 average rating, 154 reviews

A spacious living area features a flat-screen TV displaying a serene golf course scene. A comfortable blue couch and a modern lounge chair are situated around a simple coffee table. Bright light enters through windows adorned with blinds, complementing the clean, neutral decor.

Guesthouse in Naples

Coastal Cabana - 2 Miles to Beach and 5th Ave

The Coastal Cabana is an adorable one-bedroom guest house less than two miles to the beach and the best shopping and dining in Naples. This downtown location in the 34102 zip is unmatched when it comes to beach accessibility and the best of everything downtown Naples has to offer. The Cabana is tucked away in a small, quiet coastal neighborhood walking distance to the Naples Zoo and Conservancy of Southwest Florida, and Gordon River Greenway!

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 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, 123 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 Old Naples family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 113 reviews

An inviting outdoor space features a heated pool beside a hot tub, while comfortable seating arrangements are visible. A dining area is adorned with modern green chairs, and sliding doors provide access to the interior. A pink inflatable flamingo adds a playful touch to the pool area.

Home in Naples Park

2 Mstrs w Kings, Pets, Queen ensuite, hot tub, htd

A screened-in lanai features a sparkling pool and spa surrounded by sleek stone tiles. Two loungers are positioned nearby for sunbathing. A cozy seating area and dining space are visible under the protective canopy, providing a shaded retreat for relaxation.

5 out of 5 average rating, 56 reviews

Close to Everything! Stylish Home w/ Pool & Spa

4.97 out of 5 average rating, 212 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

4.95 out of 5 average rating, 132 reviews

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.

Home in Naples Park

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

A private pool is surrounded by a spacious deck, featuring two white lounge chairs positioned under a large umbrella. Lush greenery and palm trees are visible in the background, complemented by a fenced yard that adds to the secluded atmosphere.

4.89 out of 5 average rating, 106 reviews

13 Downtown Near Beach Free Heated Pool and Spa

A screened-in outdoor area features a clear blue inground pool alongside a jacuzzi, both surrounded by stone pavers. Lush greenery is visible beyond the enclosure, providing a serene backdrop. Comfortable seating awaits for relaxation in this private oasis.

4.93 out of 5 average rating, 136 reviews

Venetian Photoshoot - La Dolce Vita

4.94 out of 5 average rating, 140 reviews

An aerial view captures a spacious outdoor area featuring a swimming pool surrounded by lush greenery and palm trees. A hot tub is nestled near the pool, with lounge chairs positioned nearby. The three-story beach house is partially visible, framed by the vibrant landscape.

Guest suite in Naples

🌴🌴Green Getaway First Floor Apartment🌴🌴

An aerial view captures a resort landscape featuring four crystal blue pools, a lazy river, and a hot tub surrounded by lush greenery. Multiple lounge chairs and umbrellas are arranged poolside, enhancing the tropical ambiance. Nearby, a striking paver stone layout connects the different areas.

5 out of 5 average rating, 12 reviews

Lazy River, 4 Pools, 5th Ave Resort Personal Oasis

Family- and pet-friendly home rentals

A crystal-clear pool is surrounded by lush palm trees and greenery. Two inflatable loungers, one resembling a unicorn and another in bright pink, float gently on the water. The pool’s tile border complements the natural stone decking, providing a spacious relaxation area.

4.9 out of 5 average rating, 79 reviews

Tropical Pool Paradise close to 5th Ave/Beaches

A modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.

4.96 out of 5 average rating, 116 reviews

New Home, 6 Beds, Heated POOL / Game Room

A modern kitchen is showcased with white cabinetry, stainless steel appliances, and a large island featuring a marble countertop. Ample natural light enters through windows, illuminating the space. A dining area with wooden chairs is visible in the background, complementing the warm tones of the flooring.

4.98 out of 5 average rating, 109 reviews

Naples Retreat: Heated Pool - Minutes to Beach

A studio-style unit features a spacious bed adorned with patterned pillows. There are bedside lamps providing soft illumination, and a mirrored closet reflects the light. A cozy sofa and a colorful entertainment unit are visible, while artwork adds character to the walls.

4.93 out of 5 average rating, 119 reviews

Bamboo Oasis B - 5 miles to Beach & Downtown

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.

4.76 out of 5 average rating, 149 reviews

Bayshore Getaway

4.84 out of 5 average rating, 116 reviews

A spacious master bedroom features a king bed dressed in white linens accented by decorative pillows. Soft lighting from a bedside lamp complements the natural light filtering through sheer curtains. A cozy armchair and a wall-mounted TV enhance the comfortable atmosphere.

Cottage in Naples Park

Cozy Cottage Near Vanderbilt Beach

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.

4.95 out of 5 average rating, 130 reviews

Coastal Getaway *Heated Pool *3 King Rooms

4.93 out of 5 average rating, 14 reviews

Villa Nautilus by Downtown

Family-friendly home rentals with a pool

5 out of 5 average rating, 5 reviews

The entrance to Naples Bay Club is flanked by lush palm trees and manicured landscaping. A paved pathway leads to a grand archway, adorned with the club's name. An American flag gracefully waves in the breeze, complementing the bright blue sky.

Condo in Naples

Stunning 3 BR Condo with Pool Views near Beach

4.83 out of 5 average rating, 6 reviews

Great Condo in East Naples!

An aerial view captures the vibrant coastal community, with turquoise waters meeting sandy beaches in the distance. Palm trees and residential properties create a lush landscape. A private parking lot is visible near the foreground, indicating easy access to the beach and surrounding amenities.

4.98 out of 5 average rating, 55 reviews

Luxury condo. 300 steps to beach & Naples Pier.

A sunset view features a wooden pier stretching over waves, with silhouettes of people gathering at the end. Warm hues of orange and yellow illuminate the sky, creating a serene backdrop against the gently rolling ocean.

4.99 out of 5 average rating, 134 reviews

Beach Vacation Getaway

A sun setting over the horizon casts a warm glow on the water, creating a serene scene. The beach is lined with soft white sand, and a pier extends into the sea in the distance, framed by a clear sky above.

4.96 out of 5 average rating, 139 reviews

Beach & Pool Escape – Walk to Naples Hotspots

4.94 out of 5 average rating, 81 reviews

Naples Oasis: Cozy 2B/2BA Home w/Pool 10 Min Beach

5 out of 5 average rating, 37 reviews

A spacious screened lanai features a private pool surrounded by lounge chairs. A BBQ grill is positioned nearby, and a glimpse of the indoor living area is visible through large glass doors. Lush greenery offers a natural backdrop to this relaxing outdoor space.

Villa in Naples

Salt Pool Oasis: 5 Miles to Beaches (4BD/3BA)

The studio features a spacious bed dressed in soft linens, accompanied by a bedside lamp. An open closet with a hanging rod is visible, and natural light filters through the window, adorned with sheer curtains. A wall-mounted television is positioned across from the bed.