
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 2,900 verified reviews to help you choose

Family-friendly holiday rentals
180 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
250 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.

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).

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!

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!

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.

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.

Downtown Naples Beach Condo, Off of Famous 5th Ave
This peaceful Olde Naples condo is just half a block from dining and shops on famous Downtown 5th Ave and 4 blocks from Naples Beach. This first-floor end-unit condo is perfect for a beach getaway. This clean, modern unit has a pool just feet from the front door, a complete kitchen with updated appliances, a new washer and dryer, comfy furniture, beach chairs and umbrella, and high-speed internet. This property offers a perfect blend of relaxation and convenience to sleep up to 4 guests.

FUN AT THE BEACH
2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier (rebuilding currently) and 3rd Ave Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refrigerator.

13 Downtown Near Beach Free Heated Pool and Spa
No sargassum or seaweed on our beaches in Naples! Come to Naples for your vacation this year! Prices slashed 50% off for off season! Military discounts, first responder discounts. Great location! Just minutes to shopping and restaurants of Naples famed Fifth Avenue. We have screened in lanai, very secluded and private. Huge living room and master en-suite. Multiple units available upon request to suit large groups. Exterior cameras for safety.

Designer Naples pool home, walkable to dining
Modern 3BR/2.5BA Naples pool home in Bayshore Arts District. Sleeps 6 comfortably (up to 8 with extras). King suite, queen room, queen bunks. Garage, boat parking, washer/dryer. Walk to Ankrolab Brewing, Celebration Park, restaurants. 4 mi to beaches & 5th Ave. Close to Paradise Coast Sports Complex, US Open Pickleball, Bayview Marina. High-speed WiFi, Smart TVs, fully equipped kitchen, beach gear, coolers, grill. Naples awaits.

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!

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

Pool House+Game Room, Moments to Beach & Downtown

Naples Retreat: Heated Pool - Minutes to Beach

*New*5minto5th|Heatedpool|privateyard|10mintobeach

Modern 3BR w/ Pool & Lanai | 5 Min to Downtown

An Egret named Eddie

Backyard Oasis • Minutes to Beach & Downtown

Chic Pool Naples Beach House

Heated Pool Home, Close to Downtown
Condo rentals with a pool

Luxurious condo steps to beach with heated pool!

Beachfront fully equipped apartment

Naples Luxurious Resort Retreat with Lazy River

Lely Greenlinks Golf Resort Luxury Condo

Lely Resort Luxury Condo-1 Spectacular Pool/Golf

Lush tropical 1st floor getaway in Naples

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

Park Shore Resort258 Top Loc. View, Pool, Tennis +
Other holiday rentals with a pool

Waterfront condo in Naples 201A

Old Naples Beach Condo

Modern 5th Ave Beach Condo!

Modern & Chic 5th Ave Historic Naples

Chic resort, 4 pools, walk to 5th Ave Restaurants!

Fern Cottage! Sleeps 6! FREE Beach Parking!

Perfectly-Located Studio at Naples Beach & Town!

Blue Banyan Boathouse w/heated POOL. Boat DOCK!
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $516 AUD | $642 AUD | $625 AUD | $428 AUD | $399 AUD | $325 AUD | $321 AUD | $302 AUD | $357 AUD | $365 AUD | $428 AUD | $488 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
- Rentals with outdoor seating Old Naples
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- Apartment rentals Old Naples
- Fitness-friendly rentals Old Naples
- Rentals with a fireplace Old Naples
- Rentals with a washing machine and dryer Old Naples
- Condo rentals Old Naples
- Rentals with beach access Old Naples
- House rentals Old Naples
- Rentals with a hot tub Old Naples
- Hotel rooms Old Naples
- Waterfront rentals Old Naples
- Pet-friendly rentals Old Naples
- Rentals with a patio Old Naples
- Serviced apartment rentals Old Naples
- Rentals with an EV charger Old Naples
- Rentals with a fire pit Old Naples
- Family-friendly 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
- Bonita National Golf & Country Club
- Bowman's Beach
- Barefoot beach Bonita Springs,FL
- Jetblue Park
- The Naples Pier
- Clam Pass Park
- Big Cypress National Preserve
- Bunche Beach
- Edison & Ford Winter Estates
- Yacht Club Public Beach
- Ave Maria University
- Coral Oaks Golf Course
- Delnor-Wiggins Pass State Park
- Lovers Key State Park
- Coconut Point
- Barefoot Beach State Preserve
- Del Tura Golf & Country Club
- Tarpon Bay Beach
- Sun Splash Family Waterpark





