
Holiday rentals with a pool in Old Naples
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Old Naples
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Park Shore Resort Modern Top Floor 2 Bed 2 Bath
You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

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.

FUN AT THE BEACH
2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier( to be rebuilt)and 3rd Ave Famous 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 mattress 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 refridgerator.

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!

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!

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

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.

Sugar Beach Bungalow With a Pool!
Come jump in the pool! Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

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

Naples Retreat: Heated Pool - Minutes to Beach

Backyard Oasis - Large heated pool/Wi-fi/Lanai/PS3

An Egret named Eddie

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

Backyard Oasis • Minutes to Beach & Downtown

Venetian Photoshoot - La Dolce Vita

Walk To Beach & Shops! New 4 Bdr Pool Heated

Private Heated Pool | Playset | Near the Beach!
Condo rentals with a pool

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

Waterfront condo in Naples 201A

Beachfront fully equipped apartment

Lely Greenlinks Golf Resort Luxury Condo

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Lush tropical 1st floor getaway in Naples

Amazing Condo-1 mile from Bonita Beach

Beautiful Pool 5m to the Beach Downtown & Shopping
Other holiday rentals with a pool

Fern Cottage! Sleeps 6! FREE Beach Parking!

Pool Home Minutes to the Beach

Beautiful 2-Bed Steps to Naples Beach & Downtown!

Casa Di Napoli: 2/2 Chic Retreat/Private Pool

Naples Oasis: Private Pool | 10 Min to Beach

Villa Anna Retreat with Pool

Pink Palm Paradise-Pool/Hot Tub- Near to beach

Salt Pool Oasis: 5 Miles to Beaches (4BD/3BA)
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $503 AUD | $625 AUD | $608 AUD | $416 AUD | $389 AUD | $317 AUD | $312 AUD | $294 AUD | $347 AUD | $355 AUD | $416 AUD | $475 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 |
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 $97 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!
Destinations to explore
- Rentals with outdoor seating Old Naples
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- Pet-friendly rentals Old Naples
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- Rentals with an EV charger Old Naples
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- 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
- Bonita National Golf & Country Club
- Tigertail Beach
- Barefoot beach Bonita Springs,FL
- Heritage Bay Golf & Country Club
- Clam Pass Park
- Florida Gulf Coast University
- Bowman's Beach
- Edison & Ford Winter Estates
- Stonebridge Country Club
- Jetblue Park
- Delnor-Wiggins Pass State Park
- Esplanade Golf & Country Club of Naples
- Del Tura Golf & Country Club
- Big Cypress National Preserve
- The Naples Pier
- Barefoot Beach State Preserve
- Coral Oaks Golf Course
- Bunche Beach
- Talis Park Golf Club
- Coconut Point
- Hertz Arena





