
Vacation 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.

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.

LUXE Oasis | 10 min Beach+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!

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.

835 GulfShore Villa | Mins 2 Mercato & White Sands
Welcome to 835 GulfShoreVilla! Bask in the Florida sunshine, practice your golf swing, & explore the Gulf Coast in style when you choose this completely remodeled vacation rental! This 2BD/1.5BA Villa is just a block away from Mercato Shopping Center, where you'll unique shops, eateries, live entertainment & more. With a fully equipped kitchen, 2 Smart TVs, free WiFi, modern decor, & a peaceful location, this home invites you to kick back, relax, & enjoy!

Beautifully private homeHeated Pool/Spa and Cabana
WELCOME PICKBALLERS! We are close to Naples Community Park and downtown Naples and beaches, perfect location. Unique one of a kind property, This house has been beautifully remodeled with Stunning Carrera marble floors, upgraded 4 bedroom 2 bath home with a separate pool house suite with its own kitchen and full bath that sleeps 4 guests. Beautiful landscaped yards with amazing pool. Only minutes to the beach. Private outdoor shower.

Brookside Bungalow- Perfect 2 Bedroom House & Pool
Perfect 2 Bedroom House with a Pool only 2.5 Miles to the Beach and 1.5 Miles to Beautiful 5th Ave in Naples, FL! This House is perfect for those coming to Naples on Vacation, for work, or seasonally! Enjoy a completely private backyard with a pool, outdoor shower, and lanai! Relax in your very own private oasis within a short driving distance of all of the most popular Naples spots! This house is perfect for 1-4 guests.

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.

Southern Charmer, a handsome beach studio (Naples)
Come vacation in beautitful Naples, Florida! This guest house is perfect for a couples get away or some much needed R&R. The property boasts a pool, side yard, and is just across the street from the beach. Enjoy fine dining, shopping, and entertainment in downtown Naples located in just a 20 minute walk or 5 minute car ride.
Popular amenities for Old Naples rentals with a pool
House rentals with a pool

Tropical Modern Naples Retreat with Heated Pool

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

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

Lakefront Oasis with Heated Pool

Naples Retreat with Pool Near Beaches and 5th Ave

Private Heated Pool | Playset | Near the Beach!

Private Naples Oasis w/ Cart, Gym & Saltwater Pool

Blue Banyan Boathouse w/heated POOL. Boat DOCK!
Condo rentals with a pool

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

Beachfront fully equipped apartment

Lely Greenlinks Golf Resort Luxury Condo

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Beach Vibe Resort Condo | Pool/Golf & Near Beaches

Lush tropical 1st floor getaway in Naples

The Perfect Resort for the Vacation You Want

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

Old Naples Beach Condo

Stunning 3 BR Condo with Pool Views near Beach

Luxury condo. 300 steps to beach & Naples Pier.

The Club at Naples Cay 1101

Pool Home Minutes to the Beach

Great Location in Naples near Beach & Downtown

Lux Lakefront | 5min-Beach | 70" TVs | Pickleball

Heated Pool * *Villa Mykonos* * 2miles to Downtown
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R5,349 ZAR | R6,101 ZAR | R5,913 ZAR | R5,127 ZAR | R4,785 ZAR | R3,896 ZAR | R3,845 ZAR | R3,623 ZAR | R4,272 ZAR | R4,375 ZAR | R5,127 ZAR | R5,845 ZAR |
| 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 vacation rentals with a pool in Old Naples

Total vacation rentals
Explore 280 vacation rentals in Old Naples

Nightly prices starting at
Old Naples vacation rentals start at R1,196 ZAR per night before taxes and fees

Verified guest reviews
Over 2,730 verified reviews to help you choose

Family-friendly vacation rentals
210 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wi-Fi availability
280 of Old Naples vacation 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
- Family-friendly rentals Old Naples
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- Rentals with pools Naples
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- Naples Beach
- Captiva Island
- Lovers Key Beach
- Clam Pass Park
- Bonita National Golf & Country Club
- Heritage Bay Golf & Country Club
- Tigertail Beach
- Edison & Ford Winter Estates
- Esplanade Golf & Country Club of Naples
- Florida Gulf Coast University
- Stonebridge Country Club
- Del Tura Golf & Country Club
- Jetblue Park
- Delnor-Wiggins Pass State Park
- Talis Park Golf Club
- Bunche Beach
- Bowman's Beach
- Big Cypress National Preserve
- Coral Oaks Golf Course
- Sun Splash Family Waterpark
- Manatee Park
- The Naples Pier
- Naples Botanical Gardens
- Coconut Point




