
Vacation rentals with a pool in Naples
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Naples

Total vacation rentals
Explore 1,030 vacation rentals in Naples

Nightly prices starting at
Naples vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 18,950 verified reviews to help you choose

Family-friendly vacation rentals
860 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 290 rentals that welcome pets

Rentals with dedicated workspaces
610 properties have a dedicated workspace

Wifi availability
1,020 of Naples vacation 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!
Top-rated rentals with a pool in Naples
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

NEW! Zen Oasis w/ Pool & Spa | Walk to Beach
NEW from longtime Super Host! Escape to this spacious & serene Naples retreat, just a 15 min walk from Bluebill Beach Access. Thoughtfully designed with an open layout and generous living spaces, this chic getaway offers plenty of room to relax & unwind. Enjoy a private heated pool and spa, a fully equipped kitchen, comfortable furnishings, and inviting indoor living areas. Spend your days at the beach, lounge by the pool, and experience the best of Naples from this peaceful Zen-inspired escape.

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.

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!

Your Private NaplesBeach Getaway
🌴 Private Oasis 3 mins from Vanderbilt Beach 🌊 Welcome to our slice of paradise in Naples Park, Florida! Nestled 3 minutes away from the pristine sands of Naples Beach, world-famous Mercato Shops & Dining, and Publix/Walmart. Only 15 minute north of 5th Ave Downtown District. Our renovated home features a privately fenced backyard with new heated saltwater pool, a custom miniature golf zone, and many outdoor games for every guest 😃 Simply the perfect cozy retreat for your beach getaway⛱️

Attention Naples Lovers! Entire Home w/Pool&HotTub
Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

Oasis Naples Condo 2BR/2Bath
Soak up the warm southwest Florida sun and enjoy a clean modern home with gorgeous views. This newly renovated condo is a short 5 minute car ride to Naples Beaches and 15 minutes to downtown. Two bedroom, two full bath home is the perfect quiet place for a couple’s retreat or for working remotely with high speed internet. The main pool IS open dawn to dusk!!! It’s a two minute walk within the community! (The smaller pool by the condo is closed and still waiting for completion.)

Luxury Private Retreat with New Pool in Naples
Welcome to The Park Villa, a serene private retreat in the heart of Naples. Nestled among nature, this peaceful haven features a brand-new salt water heated pool and is just minutes from the Gulf of Mexico's beautiful beaches and vibrant downtown Naples, with its top restaurants and shops. Situated next to a regional park with the largest freshwater lake in Collier County, enjoy stunning views of the park and spot local wildlife like iguanas and tropical birds from your backyard.

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.

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!

Beach, Hot Tub & htd pool. 2 Owner Suites w 2 King
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.

Heated Salt Pool Retreat• Minutes to 5th ave Beach
Discover your sun-soaked Naples retreat — a private, family-friendly sanctuary with a year-round heated saltwater pool, lush outdoor living space, and effortless access to beaches and vibrant 5th Avenue shops. Designed for memorable days around the pool and peaceful nights under the stars, this home blends comfort, convenience, and classic Florida lifestyle.
Popular amenities for Naples rentals with a pool
House rentals with a pool

Naples Paradise Cove Luxury 4/3 Beach Home

Chic Naples Coastal Retreat – Heated Pool and Spa

Lakefront Oasis with Salt Water Pool

Coastal Getaway *Heated Pool *3 King Rooms

Newly Renovated Home Just Minutes From The Beach!

Villa510~3 En-Suites~Gulf Access, Heated spa~pool

Villa Anna Retreat with Pool

Pink Palm Paradise-Pool/Hot Tub- Near to beach
Condo rentals with a pool

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

Beachfront fully equipped apartment

Lely Greenlinks Golf Resort Luxury Condo

Lush tropical 1st floor getaway in Naples

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

Beautiful Pool 5m to the Beach Downtown & Shopping

Amazing Condo-1 mile from Bonita Beach

Park Shore Resort Modern Top Floor 2 Bed 2 Bath
Other vacation rentals with a pool

Blue Oasis!. The Perfect Getaway w/ Heated Pool!

Stylish Retreat, Walk to Beach, Pool, 2 King Beds

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

Brilliant Stays |12 PPL|Golf | Movie Theater| Pool

Waterfront Condo near Tin City |Balcony + views|

Modern 2-Story Beach Oasis | Pool & Spa

The Palm Haus

White Palm Paradise
When is the best time to visit Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $384 CAD | $501 CAD | $487 CAD | $370 CAD | $288 CAD | $278 CAD | $264 CAD | $244 CAD | $232 CAD | $253 CAD | $298 CAD | $362 CAD |
| Avg. temp | 18 °C | 20 °C | 21 °C | 24 °C | 26 °C | 28 °C | 29 °C | 29 °C | 28 °C | 26 °C | 23 °C | 20 °C |
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- Naples Beach
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- Florida Gulf Coast University
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