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.

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Guest favourite

Guest suite in Naples

5.0 out of 5 average rating, 133 reviews

By the Beach and 5th - Studio Guest Home & Pool

Great location! Newly renovated! A studio guest home with your own private entrance & your own full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining and 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 the pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth shower speaker? This home is 350 square feet of clean cuteness!

14 – 21 Dec

$3,707 AUD total

Guest favourite

Home in Naples

4.99 out of 5 average rating, 103 reviews

POOL HOUSE, CLOSE TO THE BEACH & DOWN TOWN NAPLES!

HEATED Pool home - Completely renovated home that comfortably sleeps 6 Only 5 minutes to the most desirable Beaches in the USA! Also very close to incredible restaurants, Publix, Target, Shopping, Parks and only 10 minutes to Downtown Naples. Flat-Screen TVs, Hi-Speed Internet, Comfy beds, modern and fully-stocked Kitchen. Very private and large pool with outside grill and patio furniture. Perfect for relaxing after a long day at the beach, we look forward to welcoming you to our HAPPY PLACE!

28 Oct – 4 Nov

$5,216 AUD total

Guest favourite

Home in Naples

4.95 out of 5 average rating, 43 reviews

Large Poolside Studio! Private & close to 5th Ave!

*PLEASE NOTE: Starting 5/1/24-5/15/24 the pool, patio & front yard will not be able to be used by guests* Looking for privacy and a place that’s super close to 5th Ave with a Pool? You found it!! Stay high up in the trees in your very own 2nd story studio overlooking the beautiful pool & yard! Very spacious, clean & comfortable w/ pull out couch & king bed! You’re close to the action but tucked away in your own private setting. Enjoy the pool & canal! 5-8 minute car ride/Uber to 5th Ave!

22 – 29 July

$1,898 AUD total

Guest favourite

Home in Naples Park

4.96 out of 5 average rating, 153 reviews

Luxe Beach Home! Perfect for the Whole Family

This 2,000-square foot stunner has a saltwater pool, hot tub, two-car garage, three bedrooms and four bathrooms. There are bikes and beach accessories on site to take to the beach. Guest who is booking the reservation must be 26 years or older. There is a fee of $100/night per person for any guest over 7 in total up to a maximum of 9 guests. For example, if you have 8 guests, then the extra charge will be $100 per night. Please enter the exact number of guests before completing your booking.

17 – 24 July

$5,555 AUD total

Guest favourite

Apartment in Naples

4.99 out of 5 average rating, 121 reviews

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

24 June – 1 July

$1,567 AUD total

Guest favourite

Condo in Old Naples

5.0 out of 5 average rating, 29 reviews

Downtown Naples Condo, Next to 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 3 guests.

8 – 15 July

$2,818 AUD total

Superhost

Apartment in Old Naples

4.81 out of 5 average rating, 16 reviews

Beautifully Renovated Condo, Walk to Beach/3rd St

Take a break and unwind at this peaceful oasis. Embrace the laid back lifestyle of the beach when you stay at our downtown Naples condo! The 2-bedroom, 2-bath vacation rental provides updated finishes throughout and wonderful shared amenities. Spend your mornings on the beach, dolphin watching, or perusing the farmers market. Enjoy afternoons on the beach, swimming in the heated on-site pool, or shopping on 3rd St and 5th Ave. You'll love this Old Naples location, promising endless fun!

24 Sept – 1 Oct

$5,164 AUD total

Guest favourite

Holiday home in Old Naples

4.86 out of 5 average rating, 50 reviews

4-Star/marina/on water/5th ave/pools/Naples Bay

Nightly!! One of the nicest resorts in southwest Florida, 5 pools, four star (kids pool, adult pool, lazy river, hot tub, swim pool. Completely just renovated to lasted decor, On the inland waterway, w Marina, boat rentals, full spa fitness center first class, on site restaurants, tennis courts, near beaches and popular downtown Naples, shuttles to transport you, restaurants all around and shopping, pets allowed w $75 fee Price includes the $49 a night resort fee, check out cleaning,

10 – 17 June

$4,687 AUD total

Superhost

Condo in East Naples

4.92 out of 5 average rating, 52 reviews

3 Pools, lazy river, walk to 5th ave restaurants!

Welcome to Naples finest gated 4 downtown resort, rewarding guests with a measure of privacy and serenity at Naples Bay Resort. Naples Bay Resort features an amenity rich environment with marina, waterfront dining and shopping, Euro-style spa, an expansive activity center, three crystal-blue resort pools, multiple hot tubs, meandering lazy river, and a complete fitness center. Walk to downtown 5th ave or complimentary shuttle to beaches and downtown direct to your front door.

13 – 20 Oct

$3,752 AUD total

Guest favourite

Condo in Old Naples

4.97 out of 5 average rating, 60 reviews

Gulfside Sleeper in the ❤ of Historic Old Naples

Bright, clean 2nd floor studio is ideal for 1 or 2 travellers. Minimalist design with an emphasis on comfort and relaxation is perfect for executive business travellers or sun seeking beachgoers. No car necessary. The small space is hard flooring of wood and tile. There is an open closet with hanging rod. The shower access is a bit tight, and may not be suitable for big and tall or plus sized individuals. The westward view from the window is one block from the beach sunsets.

19 – 26 July

$1,995 AUD total

Guest favourite

Condo in Naples

4.91 out of 5 average rating, 108 reviews

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

22 – 29 May

$2,652 AUD total

Superhost

Condo in Naples

4.85 out of 5 average rating, 156 reviews

Ground Floor, A+ Location Club Membership Included

Lakeside, ground floor condo, located in the prestigious World Tennis Club, with 50 acres devoted solely to beautiful landscaping and lakes. Great location in Naples with box stores, dining, Publix, CVS and Walgreens etc very close. Four miles to the beautiful Naples beach which extends for many miles. Membership is included, giving access to the larger swimming pool, hot tub, 16 tennis courts, gym, seasonal cafe, pro-shop tennis match making, etc.

13 – 20 Oct

$1,440 AUD total