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.

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Guest favorite

Guest suite in Naples

5.0 out of 5 average rating, 135 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!

Guest favorite

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!

Guest favorite

Home in Naples Park

4.96 out of 5 average rating, 155 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.

Guest favorite

Home in Naples

4.95 out of 5 average rating, 86 reviews

Lux Boho~10 min beach~Custom Pool~7 min 5th Avenue

Paradise awaits! This newly updated, family friendly 3 bed 3 bath home is just a 10-15 minute drive from our favorite local beaches: Via Miramar and Lowdermilk. *Located on a quiet street just 7 minutes from 5th Avenue!* Our screened in lanai makes our home the perfect mix of indoor/outdoor living! Lay out on our luxury chaise loungers, sip a cocktail, play a card game, take a dip in the pool, grill up some grub, kick back and relax! Our goal is to make you feel at home, but on vacation!

Guest favorite

Home in Old Naples

5.0 out of 5 average rating, 34 reviews

Luxurious Olde Naples beach House

Newly remodeled! This casually elegant 3700 sq. ft. 4 bedroom home is located in the upscale neighborhood of Olde Naples. Located just steps away from one of Naples most pristine beaches and the Naples Pier. Charmingly designed, this home boasts 25 foot ceilings and lavish windows which provide for an open and airy feel. Enjoy the large heated swimming pool in the privacy of your own backyard. Beach, restaurants and Fifth Ave and Third St. shopping all located within walking distance.

Superhost

Condo in Old Naples

4.83 out of 5 average rating, 23 reviews

Renovated Studio Steps to Naples Beach & Downtown!

Your next Sunshine State retreat begins at this beautiful Naples studio condo! Cross the street to the sunny beaches of the Gulf of Mexico, take a short stroll to the famous Naples Fishing Pier, or walk a block to Third Street South - Naples' destination venue for fine dining, casual eateries, boutiques, and galleries. After a day in the sun, relax in your second-story home-away-from-home featuring a flat-screen cable TV, free WiFi, all new furnishings, and a remodeled kitchen and bathroom.

Guest favorite

Condo in Old Naples

5.0 out of 5 average rating, 31 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.

Guest favorite

Vacation home in Old Naples

4.87 out of 5 average rating, 52 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,

Superhost

Condo in East Naples

4.92 out of 5 average rating, 53 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.

Guest favorite

Guesthouse in East Naples

4.93 out of 5 average rating, 115 reviews

Private & Spacious Studio 1 mile fr 5th Ave w/Pool

Welcome to Kevin's Newly Renovated Air BNB in Naples, featuring a private swimming pool, patio w/sun shade, parking, luxury sheets, fully stocked kitchen, full size W/D, and more! This uber-quiet and private space is located just over 1 mile from 5th Avenue/downtown Naples, & 2 miles from the beach. 5 minute walk to Naples Bay Resort, coffee shops & restaurants. Walk or use complimentary bikes to check out nearby Celebration Park, a brewery, Market 360, & pickleball courts!

Guest favorite

Condo in Old Naples

4.97 out of 5 average rating, 62 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.

Guest favorite

Condo in South Naples

4.94 out of 5 average rating, 99 reviews

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.