
Holiday rentals with a pool in Old Naples
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Old Naples

Total holiday rentals
Explore 260 holiday rentals in Old Naples

Nightly prices starting at
Old Naples holiday rentals start at $100 AUD per night before taxes and fees

Verified guest reviews
Over 3,000 verified reviews to help you choose

Family-friendly holiday rentals
170 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
120 properties have a dedicated workspace

Wi-Fi availability
260 of Old Naples holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Naples rentals

4.9 Average rating
Old Naples stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Old Naples
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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.

Downtown Condo at Naples Pier Beach
Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

Lux Oasis | HTD Pool•10 min Beach and 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!

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).

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!

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning
🏡 THIS LUXURY PROPERTY IS IDEAL FOR FAMILIES/SMALL GROUPS (SLEEPS 8) YOU HAVE MADE IT! You are now viewing one of the most unique properties in Naples 🌴 & here is why: 🌳 This property is on 2.5 acres of land & VERY private 🏖️ Beach is only 12 minutes away 🍽️ 10 minutes from heart of the city (Dining, shopping, nightlife) 🏊♂️ Heated saltwater pool/spa ⛳ Golf putting green 🎾 2 Pickleball Courts 🏓 Ping Pong table W/AC in garage 🏀 Adjustable Basketball Hoop 💻⚡ Blazing fast WIFI

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.

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.

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.

Naples Retreat: Heated Pool - Minutes to Beach
We know that you’ll love it here – whether you spend your time lounging by our pool, or at Naples’ world-renowned beautiful beaches. The home is only 10 minutes away from downtown Naples, which features some of the very best restaurants in Florida. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. As this is our own vacation home, we’ve made every effort to make it as comfortable and convenient as possible.

Private Pool · 4 mi to Beach · Walk to Dining
Private Naples pool home with direct pool access from the main bedroom and living area. Beach in the morning, your own open-air pool in the afternoon, then walk to dining, coffee, breweries, and Celebration Park food trucks and live music. Four miles to Gulf beaches, 5th Avenue South, and downtown. Sleeps 6 comfortably, (up to 7 total with added fee), all on one level. BBQ grill, beach gear, Smart TVs, Pack ’n Play, high chair, and possible boat/trailer parking.

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!
Popular amenities for Old Naples rentals with a pool
House rentals with a pool

Sunside House, 3/2 Pool Home in Gated Community

Pool House+Game Room, Moments to Beach & Downtown

An Egret named Eddie

675 FantaSea | New Heated Resort Pool & Fire Pit

The WaterSun Oasis - Luxury Private Pool & Spa

Heated Pool + Lanai | 10 min Beach | Game Room

TERRA-NOVA| Pool, Sun Ledge, 10 Min to Beach/5th

Modern Oasis | Heated Pool | Near Naples Beach
Condo rentals with a pool

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

Fun At The Beach

Lush tropical 1st floor getaway in Naples

Beachfront fully equipped apartment

Lely Greenlinks Golf Resort Luxury Condo

Beautiful Pool 5m to the Beach Downtown & Shopping

Park Shore Resort258 Top Loc. View, Pool, Tennis +

Park Shore Resort-Deluxe Condo 1st FloorBLDGE #134
Other holiday rentals with a pool

Waterfront Condo near Tin City |Balcony + views|

Best Beach, Dining & Shopping! 1.5 Blocks-beach!

Naples Luxurious Resort Retreat with Lazy River

Downtown Naples Beach Condo, Off of Famous 5th Ave

Modern 5th Ave Beach Condo!

Renovated Studio Steps to Naples Beach & Downtown!

Old Naples Beach Condo

Chic resort, 4 pools, walk to 5th Ave Restaurants!
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $515 AUD | $640 AUD | $623 AUD | $427 AUD | $398 AUD | $324 AUD | $320 AUD | $301 AUD | $355 AUD | $364 AUD | $427 AUD | $486 AUD |
| 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 |
Destinations to explore
- Condo rentals Old Naples
- Apartment rentals Old Naples
- House rentals Old Naples
- Rentals with a fireplace Old Naples
- Rentals with a patio Old Naples
- Serviced apartment rentals Old Naples
- Rentals with beach access Old Naples
- Family-friendly rentals Old Naples
- Rentals with a fire pit Old Naples
- Pet-friendly rentals Old Naples
- Waterfront rentals Old Naples
- Hotel rooms Old Naples
- Rentals with a hot tub Old Naples
- Beach house rentals Old Naples
- Rentals with pools Naples
- Rentals with pools Collier County
- Rentals with pools Florida
- Rentals with pools United States
- Naples Beach
- Captiva Island
- Lovers Key Beach
- Tigertail Beach
- Florida Gulf Coast University
- Bowman's Beach
- Barefoot beach Bonita Springs,FL
- Bonita National Golf & Country Club
- Jetblue Park
- Big Cypress National Preserve
- The Naples Pier
- Edison & Ford Winter Estates
- Clam Pass Park
- Yacht Club Public Beach
- Bunche Beach
- Ave Maria University
- Coconut Point
- Delnor-Wiggins Pass State Park
- Lovers Key State Park
- Coral Oaks Golf Course
- Barefoot Beach State Preserve
- Tarpon Bay Beach
- Del Tura Golf & Country Club
- Seminole Casino Hotel Immokalee





