
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.

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 a new heated saltwater pool, a custom miniature golf zone, and many outdoor games for every guest ❤️ Simply the most perfect cozy retreat for your beach getaway🏖️

Lush tropical 1st floor getaway in Naples
Whether you're looking for a family-oriented or quiet, romantic vacation, we've got you covered! Our unit is tucked away at the south end of our complex where the trickle of the waterfall outside your lanai is the perfect backdrop to enjoying your morning coffee or perhaps a vacation cocktail! Our unit is completely remodeled in an updated coastal-chinoiserie style that is a combo of classic and contemporary, but also livable (we have two young children). Perfect backdrop to your time in SW FL!

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.

LUXE Oasis | HTD Pool •10 min Beach +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!

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!

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.

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.

Luxe Unique: Close to Beach, Hot Tub, Heated Pool
Step into the luxurious 2BR 2BA oasis in the heart of Bonita Springs, FL. It promises a relaxing retreat just a few minutes from the pristine Bonita Beach, restaurants, shops, exciting attractions, and natural landmarks. The stylish design and a rich amenity list will leave you in awe. ✔ 2 Comfortable Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Backyard (Pool, Hot Tub, Swim-Up Bar, BBQ) ✔ Lounge Pool House ✔ Workspace ✔ Smart TVs ✔ Wi-Fi ✔ Parking See more below!

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.

675 FantaSea | New Heated Resort Pool & Fire Pit
Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.

Cozy studio 1.3 miles to Barefoot Beach
Very inexpensive way to get close to the beach and still have complete privacy! Whole unit-Share nothing. Small and cozy studio/room 12x19 with a refrigerator, microwave, air conditioner, full bath, suitable to more or less sleep. Queen size bed. Closet and dresser. This is a separate guest room with a private entrance not connected to another unit. Located in an adorable tropical feel complex in a seafoam green building.

Casa Bonita - Relax @ The Beach (Newly Remodeled)
Beach within steps of this beautifully remodeled condo! DOC's restaurant & jet ski rentals, directly across the street. Beach gear available along with a cart to transport. Luxurious king size bed with extra plush mattress topper. Queen size sofa bed. Our studio will sleep up to 3 people (2 adults, 1 child) Newly refurbished pools opened April 2nd 2025.
Popular amenities for Naples rentals with a pool
House rentals with a pool

Gulf Haven Hideaway: Naples 4BD Oasis - Pool + Spa

Naples Chic Retreat | Heated Pool | Prime Spot

1 Mile to Beach! Pool, King Bed, BBQ, Games

The Marquee of Naples

Beautiful pool house 2mi from the Beach, Bikes+BBQ

Beach & Pool Escape – Walk to Naples Hotspots

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

LUXE: Beach Home w/ Screened Pool & Spa, BBQ
Apartment rentals with a pool

Bonita Beach and Tennis 1903

Beachfront fully equipped apartment

Gulf Water Views + 2 bikes, beach gear weekly stay

85" TV, World Tennis Club, Beach 4mi, Sauna

Oceanview unit. Completely remodeled pool is open!

Sunset on the balcony

Perfectly-Located Studio at Naples Beach & Town!

Bonita Beach and Tennis 3907 - Ocean Views
Other holiday rentals with a pool

Blue Haven - Heated Salt Pool/Spa, Walk to Beach!

Beachy Escape: 2BR/2BA w./ Pool, Gym, and Theater

Modern 2-Story Beach Oasis | Pool & Spa

Waterfall/Seasonally Heated Private Pool In Naples

Naples Oasis: Heated Pool 85F & 10 Min to Beach

Luxe Sunset Splash, Epic Pool, Hot Tub, Beaches

Heated Pool+Spa +2 Kings*2 miles to Beaches*Bikes

Central Charming Studio
When is the best time to visit Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £190 | £229 | £238 | £186 | £149 | £138 | £142 | £131 | £125 | £131 | £146 | £186 |
| 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 |
Quick stats about holiday rentals with a pool in Naples

Total holiday rentals
Explore 1,060 holiday rentals in Naples

Nightly prices starting at
Naples holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 17,280 verified reviews to help you choose

Family-friendly holiday rentals
870 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 300 rentals that welcome pets

Rentals with dedicated workspaces
640 properties have a dedicated workspace

Wifi availability
1,060 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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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Marco Island Public Beach Access
- Clam Pass Park
- Bonita National Golf & Country Club
- Heritage Bay Golf & Country Club
- Tigertail Beach
- Esplanade Golf & Country Club of Naples
- Gasparilla Island State Park
- Bunche Beach
- Edison & Ford Winter Estates
- Del Tura Golf & Country Club
- Talis Park Golf Club
- Manatee Park
- Stonebridge Country Club
- Delnor-Wiggins Pass State Park
- Coral Oaks Golf Course
- Big Cypress National Preserve
- Sun Splash Family Waterpark
- Bonita Beach Dog Park
- Coconut Point
- Four Mile Cove Ecological Preserve
- Florida Gulf Coast University




