
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.

New Home, 6 Beds, Heated POOL / Game Room
Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

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.

Beach Vacation Getaway
Great for a couple with 1 -2 young kids or a getaway for 2 or a business traveler. Guesthouse is totally separate from the main house. Bedroom-king sized bed. Couch, 24 inch high twin air mattress and ottoman w/ twin sized bed. Fully screened lanai/Indoor HEATED private pool/w 8ft wall (swim at your own risk). No pets. WiFi/cable TV. 10 minute drive to the beach/shopping. Walking/biking/jogging path. 4 bikes-(ride at your own risk)/BBQ grill/continental breakfast/a variety of snacks/beverages

LUXE Oasis | 10 min Beach • HTD Pool+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!

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.

Pool Bikes & Beach | Paddle Board Included
We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Beautiful Pool 5m to the Beach Downtown & Shopping
**Condo - Naples Modern Retreat** Welcome to Naples Modern Retreat, a fully renovated 2 bedroom, 2 bathroom condo nestled in a Tennis Resort in the heart of Naples, Florida. 6 miles to downtown and the beaches. This property offers a harmonious blend of scenic views including beach, canal, garden, lake, marina, ocean, pool, and resort vistas, ensuring a stay full of breathtaking beauty and modern luxury. ** Popular Amenities ** 2 bicycles, 5 beach chairs and umbrella

Walk to Vanderbilt Beach, Pets, 2 Mstrs w Kings
Fabulous 500 block location. Just a short walk/bike ride to the beach. This exclusive layout w 2 master suites, large walk-in closets, and private baths. Every living space has been thoughtfully designed for large groups of 8-10 to gather and enjoy. The house is fully stocked. This includes a coffee maker, dishes, pots and pans, beach cruiser bikes, beach chairs, a wagon, etc. All you need is to pack your bags, sit back and relax...

Beach & Pool Escape – Walk to Naples Hotspots
Modern 3BR/2.5BA Naples home with private pool, perfect for adults seeking comfort and fun. Sleeps 6 with king suite, queen room, and queen-over-queen bunks. Relax poolside or head to the beach with provided chairs, umbrellas, blankets, and coolers. Walk to Botanical Garden, breweries, and dining. High-speed WiFi, Smart TVs, and desks keep you connected if needed. Kid-ready with Pack ’n Play, high chair, and toys.

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

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

Chic Pool Naples Beach House

Lux Prvte Fam Home Pool Pcklbl Mins 2 Beach/Dning

Coastal Getaway *Heated Pool *3 King Rooms

Tropical Retreat Close to Downtown Naples & Beach

Palm Breeze

Private Oasis in the ♥ of Naples ☀Heated Pool/Spa☀

Sunny Naples Escape | Poolside + Beach Access
Condo rentals with a pool

Renovated Studio Steps to Naples Beach & Downtown!

2/2 Lovely Home away from home.

Lush tropical 1st floor getaway in Naples

Modern design 1st Flr Unit- 5 Min to Naples BEACH

The Club at Naples Cay 501 - Gulf Views

Park Shore Resort, Top Floor BLDGH #347-Lake view

Renovated Beautiful Condo In Tropical Paradise

Bonita Beach and Tennis 3907 - Ocean Views
Other vacation rentals with a pool

Tropical Dream 2BR/2BA w./ Pool, Gym, and Theater

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

Luxurious 4-Bed Pool Home with Dock & Gulf Views,

Sunset on the balcony

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

Walk To Beach & Shops! New 4 Bdr Pool Heated

Beach Retreat House (Pool & Spa)

The Coral in Lely Resort 2 Kings-Heated Pool to 89
When is the best time to visit Old Naples?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $441 CAD | $503 CAD | $488 CAD | $423 CAD | $395 CAD | $321 CAD | $317 CAD | $299 CAD | $352 CAD | $348 CAD | $388 CAD | $411 CAD |
| 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 240 vacation rentals in Old Naples

Nightly prices starting at
Old Naples vacation rentals start at $85 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wifi availability
230 of Old Naples vacation rentals include wifi 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!
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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
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- The Club at The Strand
- Bonita National Golf & Country Club
- Tigertail Beach
- Heritage Bay Golf & Country Club
- Spanish Wells Country Club
- Morgan Beach
- Seagate Beach Club
- Cypress Woods Golf & Country Club
- The National Golf & Country Club Ave Maria
- Panther Run Golf Club
- LaPlaya Golf Club
- Worthington Country Club
- The Quarry Golf Club Naples
- Esplanade Golf & Country Club of Naples
- Gasparilla Island State Park
- Park Shore Beach Park
- Sanibel Island Northern Beach
- Del Tura Golf & Country Club
- Spring Run Golf Club




