Holiday rentals with a pool in Naples

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Naples

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
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.
Home in Naples
4.95 out of 5 average rating, 117 reviews

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

Guest favourite
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.
Home in Naples
4.96 out of 5 average rating, 103 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.

Top guest favourite
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.
Flat in Naples
4.99 out of 5 average rating, 134 reviews

Beach Vacation Getaway

Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

Top guest favourite
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.
Home in Naples Park
4.97 out of 5 average rating, 204 reviews

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

This 2,000-square foot stunner has a saltwater pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

Guest favourite
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
4.95 out of 5 average rating, 133 reviews

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

Top guest favourite
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.
Home in Naples
5 out of 5 average rating, 24 reviews

Pool Home Minutes to the Beach

Enjoy our family’s bright, renovated home and experience indoor/outdoor Florida living at its best! The open floor plan living area has high vaulted ceilings and fully-retractable glass sliders that open out to a beautiful, south-facing lanai featuring a brand-new, heated, salt-water pool complete with a waterfall-edge spa, a sun shelf and in-pool loungers! Perfect for entertaining and outfitted with all new outdoor furniture including a new sofa & lounge chairs, dining table & grill.

Top guest favourite
The outdoor area features a heated saltwater pool, accompanied by a hot tub. A large blue umbrella provides shade over a sun lounger and a decorative side table. Lush palm trees and greenery surround the pool, enhancing the serene environment.
Home in Naples Park
5 out of 5 average rating, 35 reviews

Naples Park Luxury New Construction

Welcome to "The Endless Summer House"! Enjoy a luxury & stylish experience at this New Construction home, ideally located in the 500 block of the Naples Park neighborhood. We have fully stocked this home with all the amenities you'll need while visiting paradise! It's also a quick bike ride or walking distance to both Vanderbilt Beach & Delnor-Wiggins Pass State Park! This home was built new in 2023 by my company TTM Development, so we're certain you'll absolutely enjoy your stay!

Top guest favourite
An open living area features a cozy seating arrangement with a brown armchair and a textured ottoman. Wall art depicting botanical themes complements the neutral walls. A modern kitchen bar with three stools is visible, lending to the inviting and functional design of the space.
Home in Naples Park
4.99 out of 5 average rating, 148 reviews

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Top guest favourite
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.
Apartment in Naples
4.92 out of 5 average rating, 131 reviews

Beautiful Pool 5m to the Beach Downtown & Shopping

**Condo - Naples Modern Retreat** Welcome to Naples Modern Retreat, a fully renovated 2 bedroom, 2 bathroom condo nestled in a Tennis Resort in the heart of Naples, Florida. 6 miles to downtown and the beaches. This property offers a harmonious blend of scenic views including beach, canal, garden, lake, marina, ocean, pool, and resort vistas, ensuring a stay full of breathtaking beauty and modern luxury. ** Popular Amenities ** 2 bicycles, 5 beach chairs and umbrella

Top guest favourite
A spacious outdoor area features a refreshing pool with gently rippling water. Two pink floatation devices rest on the water's surface. Light-colored lounge chairs are positioned nearby, and the house is framed by lush greenery, creating an inviting space for relaxation.
Home in Naples
5 out of 5 average rating, 24 reviews

Waterfront w/Pool & Patio - Close to Everything

Discover your perfect Naples getaway at our charming canal-front home. Featuring 3 bedrooms & 2 bathrooms, this retreat offers a private dock for kayaking and fishing adventures right from your backyard. Relax by the refreshing pool, or enjoy alfresco dining on the spacious patio. You'll have easy access to pristine beaches, delicious dining, and all the best Naples has to offer. Experience the tranquility and beauty of waterfront living in this idyllic setting.

Top guest favourite
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.
Home in Naples Park
4.97 out of 5 average rating, 112 reviews

The WaterSun Oasis - Luxury Private Pool & Spa

The WaterSun Oasis is a 3 bedroom, 2 1/2 bath home, perfect for family or friends to get away. Less than one mile from Vanderbilt Beach, this high-quality private house, equipped with a top-notch outdoor pool area, is packed with best-in-class amenities to set your experience apart from others. Located just 30-minutes from RSW International Airport and surrounded by multiple beaches, restaurants, shopping centers, night life and more. Book your stay today!

Top guest favourite
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
4.98 out of 5 average rating, 115 reviews

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

The perfect home for a beach vacation just a 6 min bike ride to the beach and 2 master suites with king beds, walk-in closets, TVs, and private baths, 1 ensuite with a Queen bed, and the 4th bedroom with twin beds. Even a pool bath and outdoor shower! A large chef's kitchen with all Bosch appliances. Every space is designed for a group of 8-10 to gather. Bikes, towels, beach chairs, toys are all included! Great for large groups of 8-10 to gather and enjoy.

Popular amenities for Naples rentals with a pool

When is the best time to visit Naples?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$332 SGD$401 SGD$415 SGD$325 SGD$260 SGD$240 SGD$248 SGD$229 SGD$218 SGD$229 SGD$255 SGD$325 SGD
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Quick stats about holiday rentals with a pool in Naples

  • Total holiday rentals

    Explore 1,000 holiday rentals in Naples

  • Nightly prices starting at

    Naples holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    830 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 250 rentals that welcome pets

  • Rentals with dedicated workspaces

    590 properties have a dedicated workspace

  • Wifi availability

    990 of Naples holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Naples rentals

  • 4.8 Average rating

    Naples stays are highly rated by guests – averaging 4.8 out of 5!

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