Holiday rentals with a pool 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.

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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, 160 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!

ValueFamilyParks

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, 156 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).

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An outdoor pool area is presented within a screened enclosure, featuring a clear blue pool. Two chaise lounges with towels sit alongside the pool, and lush greenery frames the space, providing a serene backdrop under a partly cloudy sky.

4.92 out of 5 average rating, 115 reviews

Elegant house w/heated Private Pool

House has an open layout and a peaceful atmosphere. Step out to the pool for a refreshing swim and enjoy outdoor dining. Roku TVs in Living Room and in each bedroom, ceiling fans in all rooms. A pet friendly (extra charge)and work-friendly accommodation with high-speed internet. Fully equipped, laundry room with provided laundry essentials. The kitchen is fully stocked. Coffee machine, toaster, Ninja Professional Blender to make refreshing cocktails. All the comforts of your own home!!!

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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

Indulge in Old Florida with our Boho Chic estate combining mid-century modern esthetics with tropical flare. Complete with a whole house Reverse Osmosis system, a heated saltwater pool + spa, a sprawling carefully maintained property with hundreds of mature trees, you can enjoy Florida living in privacy and style. You might even spot some wildlife! You'll have a beautiful master suite, a fully equipped kitchen, a 75" smart TV, several dedicated desks, a Weber grill, a fire pit, and more.

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4.98 out of 5 average rating, 121 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 North Naples

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, 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.

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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, 168 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.

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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, 145 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!

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4.92 out of 5 average rating, 106 reviews

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

Have fun with the whole family in this stylish place. This luxury 5 bedroom pool home home getaway is close to everything Naples has to offer! Beaches shopping and restaurants are all within minutes of this home. 5 bedrooms gives plenty of room for everyone! The open concept kitchen, dining area and living room keeps the conversation flowing in the cool A/C! The outdoor dining table turns into shuffleboard and bowling in-between dips in the oversized pool.

LocationFamilyNearby

4.99 out of 5 average rating, 155 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...

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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.

4.89 out of 5 average rating, 139 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!

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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, 142 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.

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Popular amenities for Naples rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 106 reviews

Home in Bonita Beach

"The Mac" Beach House! Premier Location! Pool/Spa

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A large, A-frame house is shown with a stone façade and expansive front windows. Lush greenery surrounds the entrance, and a paved driveway leads to the home. The roof slopes gracefully, complemented by wooden beams and a welcoming front door.

4.95 out of 5 average rating, 312 reviews

Cathedral Heights

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An inviting lounge area features a spacious layout with contemporary furnishings. Natural light floods the room through large glass doors that open to a private swimming pool. Decorative plants enhance the aesthetic, while a modern kitchen is visible in the background.

4.92 out of 5 average rating, 99 reviews

The Lounge| Modern,Pool, Privacy, 10min Beach/5th

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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.

4.95 out of 5 average rating, 107 reviews

Attention Naples Lovers! Entire Home w/Pool&HotTub

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4.96 out of 5 average rating, 102 reviews

Luxury Private Retreat with New Pool in Naples

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4.95 out of 5 average rating, 174 reviews

Private Pool · 4 mi to Beach · Walk to Dining

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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

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An aerial view showcases a private backyard with a sparkling swimming pool and a hot tub. A white umbrella provides shade over a lounged area, with comfortable seating options visible nearby. Lush green grass surrounds the pool area, enhancing the outdoor space.

4.86 out of 5 average rating, 59 reviews

Your Perfect Escape in the Heart of South Naples

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Apartment rentals with a pool

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.

4.92 out of 5 average rating, 137 reviews

Perfectly located Old Naples condo

LocationFamilySleep quality

4.9 out of 5 average rating, 186 reviews

Downtown Condo at Naples Pier Beach

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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.

4.92 out of 5 average rating, 142 reviews

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

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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.

4.93 out of 5 average rating, 102 reviews

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

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A cozy living area features a spacious light-colored sofa and two armchairs, complemented by a glass-topped coffee table. A ceiling fan provides airflow, while natural light pours in through large glass doors. A television is mounted on the wall, enhancing the room's functionality.

4.94 out of 5 average rating, 120 reviews

Lush tropical 1st floor getaway in Naples

LocationFamilyLong stay

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, 129 reviews

Fun At The Beach

LocationValueIndoor spaces

4.96 out of 5 average rating, 341 reviews

A spacious pool area is surrounded by lush palm trees and vibrant flowers. The water is calm, with small fountains creating gentle ripples. Loungers line the pool's edge, inviting relaxation under the sun. Sunlight reflects off the surface, enhancing the serene atmosphere.

Apartment in Lely Resort

Lely Greenlinks Golf Resort Luxury Condo

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A bright living and dining area features a white dining table set with blue accents. A comfortable light-colored sofa is positioned nearby, inviting relaxation. Large sliding glass doors provide views of the balcony and surroundings, allowing natural light to fill the space.

4.93 out of 5 average rating, 111 reviews

Park Shore Resort Beautiful Top Floor 2 Bed 2Bath

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Other holiday rentals with a pool

An outdoor balcony features a round dining table surrounded by several chairs, offering stunning views of the ocean and a glowing sunset. The serene atmosphere is enhanced by soft colors in the sky, while a small table stands beside a chair.

5.0 out of 5 average rating, 24 reviews

The Club at Naples Cay 1101

LocationFamilyHospitality

5.0 out of 5 average rating, 70 reviews

An outdoor dining area is highlighted by a large wooden table surrounded by woven chairs. Pendant lights hang above, casting soft illumination. A swimming pool with clear water is visible through a screened enclosure, complemented by lush greenery in the background.

Home in South Naples

Mediterranean Inspired Villa with Private MiniGolf

ValueLocationAccess

The exterior view showcases a modern two-story villa with large windows, overlooking a private heated pool and spa. Comfortable seating is arranged by the poolside. Lush greenery lines the perimeter, creating a serene outdoor space for relaxation and enjoyment.

4.96 out of 5 average rating, 28 reviews

*New* Naples Villa w/ Pool Jacuzzi | Sleeps 14

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Luxe

A tranquil backyard scene showcases a private pool surrounded by lush tropical foliage. Amenities include comfortable outdoor seating, a dining area, and a nearby outdoor kitchen. A colorful assortment of pool floaties adds a festive touch, set against a stunning sunset sky.

5.0 out of 5 average rating, 44 reviews

LUXE: Custom Beach Home w/Pool&Spa, Fire Pit, BBQ

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5.0 out of 5 average rating, 22 reviews

Casa Blanca Gated Villa Heated Pool & Spa Near 5th

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Superhost

An aerial view reveals a private pool surrounded by a spacious patio. Colorful umbrellas provide shade over lounge areas, while landscaped gardens with lush greenery add to the outdoor aesthetic. A shaded area with a sail-like structure overlooks the pool, enhancing the inviting setting.

4.83 out of 5 average rating, 64 reviews

The Heron: Poolside Paradise

FamilyValueAir conditioning

Luxe

5.0 out of 5 average rating, 8 reviews

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

LocationFamilyCleanliness

The living area showcases a light-filled space with a comfortable seating arrangement, including a large sectional sofa and accent chairs. A round coffee table is positioned on a soft area rug. Large sliding glass doors lead to a private balcony with views of the Gulf.