
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.

Lely Greenlinks Golf Resort Luxury Condo
This beautiful and spacious 2-bedroom, 2 bath condo is luxurious, impeccably clean, well-stocked - and perfect for your next vacation getaway! Greenlinks Golf Resort is situated within the prestigious Lely Resort Golf & Country Club in Naples. It is just a two minute walk over to the clubhouse where you can tee off on the Lely Flamingo or Mustang golf courses. Ideal central location between downtown Naples and Marco Island, you are just 15 minutes from downtown or beaches in either location.

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.

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!

Beach House on pond w/ HEATED pool - sleeps 6
This secluded and beautiful beachside getaway is yours. Perfectly positioned easy access to white-sand beaches & fabulous shopping/dining/golfing/site seeing experiences of Naples. (2 bed 2 bath.) Gorgeous lakeview, (turtles/ducks incl.). HEATED POOL. Enjoy fresh coffee at sunrise from lanai watching swans take their morning swim or have a nightcap near shimmering moonlit pond. We warmly welcome you to rest, relax and stretch-out at this incredibly charming Beach*House cottage.

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.

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.

555 Royal Palm Villa | Luxury Heated Pool Home
Luxury resides at this 3 Bed/2 Bath with Heated Pool. You'll surely be happy spending your stay at this single family home located on the most desired block of the popular Naples Park neighborhood, only a 3 minute drive from Vanderbilt Beach and Wiggins Pass Beach. Xfinity Comcast Cable & Internet service Free to our guests. Beach chairs, umbrellas and towels are available to make your trip to the beach an easy one.
Popular amenities for Old Naples rentals with a pool
House rentals with a pool

Naples Retreat: Heated Pool - Minutes to Beach

Last Minute Deals! Walk to beach! Jacuzzi & Pool

Woodridge: Work Friendly, Pool, Near Beach

Naples Retreat with Pool Near Beaches and 5th Ave

Private Heated Pool | Playset | Near the Beach!

New Vacation Home, Heated Pool, Tennis, Basketball

Blue Banyan Boathouse w/heated POOL. Boat DOCK!

Private Oasis in the ♥ of Naples ☀Heated Pool/Spa☀
Condo rentals with a pool

Lely Resort Luxury Condo-2 Spectacular Pool/Golf

Bonita Beach and Tennis 1903

Luxurious condo steps to beach with heated pool!

Ft Myers Beach & Lovers Key State Park- FANTASTIC!

Cool Condo for your Cozy Stay in Lely Resort

Luxury condo. 300 steps to beach & Naples Pier.

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

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

RARE FIND! New Renovated Home on Golf Course!

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

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

Designer Naples Home w/ Heated Pool & Spa

Lakefront Oasis with Heated Pool

Downtown Naples Oasis – 5 Mins to the Beach!

Hidden Gem-Central Naples-3 Miles to Town & Beach

Custom Naples 3BDRM Luxury Home/Htd Pool/SuperClean
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 269 | € 307 | € 298 | € 258 | € 241 | € 196 | € 194 | € 183 | € 215 | € 220 | € 258 | € 294 |
| 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 € 60 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
- Waterfront rentals Old Naples
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- Pet-friendly rentals Old Naples
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- Rentals with a fire pit Old Naples
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- Beach house rentals Old Naples
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- Hotel rooms Old Naples
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- 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
- Clam Pass Park
- 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
- Hertz Arena
- Sun Splash Family Waterpark
- Manatee Park
- The Naples Pier
- Coconut Point




