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.

4.96 out of 5 average rating, 201 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 private patio area features a smooth surface bordered by lush tropical plants and colorful flowers. A three-tiered blue water fountain adds a calming element, accompanied by comfortable seating arrangements. The space is set against a backdrop of vibrant greenery, presenting a serene outdoor escape.

4.97 out of 5 average rating, 410 reviews

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

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!

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 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, 111 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!

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, 150 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, 114 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.

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

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.

4.94 out of 5 average rating, 109 reviews

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

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, 329 reviews

Coastal Farmhouse w/ mini Golf, Private Beach &Spa

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

4.89 out of 5 average rating, 106 reviews

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.

Apartment in Naples

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.

4.94 out of 5 average rating, 142 reviews

Venetian Photoshoot - La Dolce Vita

4.98 out of 5 average rating, 172 reviews

A compact living area features a light-colored sofa and wooden accents. A sturdy ladder leads to a lofted sleeping area. Natural light fills the space, highlighting a well-equipped kitchenette with modern appliances and a small dining area. A door offers access to the outside.

Tiny home in Cape Coral

Private Hot Tub | King Bed Loft | Hammock Swings

4.92 out of 5 average rating, 131 reviews

A modern living area is highlighted by a white sectional sofa and a circular glass dining table surrounded by stylish white chairs. Large windows provide views of a tranquil outdoor space with greenery and water, complementing the bright interior decor.

Condo in Naples

Beautiful Pool 5m to the Beach Downtown & Shopping

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, 292 reviews

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

Family- and pet-friendly home rentals

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, 122 reviews

Bamboo Oasis B - 5 miles to Beach & Downtown

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, 170 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, 156 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, 131 reviews

Newly Renovated Studio 5 Min From Beach

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.

4.93 out of 5 average rating, 100 reviews

Luxury Design/Water-Heater-Pool/Pet friendly

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, 134 reviews

Coastal Getaway *Heated Pool *3 King Rooms

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.

4.83 out of 5 average rating, 183 reviews

Charming cottage bay area

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

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

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

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

A spacious outdoor pool area is presented under clear blue skies, featuring a sparkling pool and a spa. Lounge chairs are arranged around the poolside, offering a relaxing space to unwind. Lush palm trees are visible in the background, enhancing the tropical ambiance.

4.94 out of 5 average rating, 17 reviews

Olde Naples 5th Ave S Penthouse

4.92 out of 5 average rating, 166 reviews

A spacious living area features modern white armchairs positioned beside a stylish sofa. A table is set with decorative placements, and light enters through large sliding glass doors, framing views of lush greenery outside.

Condo in Park Shore

Park Shore Resort Modern Top Floor 2 Bed 2 Bath