Vacation rentals with a pool in Old Naples

4.96 out of 5 average rating, 110 reviews

A modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.

Home in South Naples

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.

4.99 out of 5 average rating, 134 reviews

A spacious outdoor area features a heated pool bordered by a tiled deck. Comfortable lounge chairs are positioned around the pool, alongside a table and chairs. Large sliding glass doors provide access to the interior spaces, and a grill is located under the screened enclosure.

Home in Naples

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!

A modern kitchen features white cabinetry and a spacious island with white quartz countertops. Stainless steel appliances, including a microwave and oven, are visible. A television displaying a beach scene adds a touch of relaxation, while natural light fills the open layout.

5 out of 5 average rating, 25 reviews

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a 1 BR beach rental condo in the heart of Old Naples, FL, and is perfectly situated a 1/2 block off famous 5th Avenue lined with restaurants and shops and 4 short blocks to the beach. The condo is located in a charming "Old Florida" building surrounded by multi-million dollar estates with a heated pool in the courtyard. The unit is equipped with high speed wifi and has a dedicated work space and desk in the unit. There is a wifi enabled keypad to ensure simple contactless entry!

An open living area features light-colored furnishings and natural décor elements. A dining table is set with woven placemats, while large glass doors provide access to a balcony with a view of the marina. Soft textiles enhance the inviting atmosphere.

4.89 out of 5 average rating, 19 reviews

Downtown Marina Retreat

Welcome to our flawlessly remolded condo in Naples, FL, featuring a king and queen bed both with en-suites. With a perfect view of the marina you'll feel like you're in paradise. Located just 2 blocks from 5th Ave and less than a mile from the beach, it's the ideal place for a relaxing getaway. The downstairs suite offers a serene peaceful view and coffee maker and microwave. Our unit includes a wine refrigerator, covered parking, pool/spa washer/dryer, tandem bike, pickleball paddles, and more!

The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.

4.98 out of 5 average rating, 109 reviews

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.

4.94 out of 5 average rating, 126 reviews

A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.

Home in Naples

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!

4.96 out of 5 average rating, 122 reviews

A screened lanai houses a heated pool surrounded by a spacious deck. Comfortable seating areas provide space for relaxation. Vibrant tropical plants line the backyard, creating a serene environment. Natural light enters from various angles, enhancing the area's inviting ambiance.

Home in East Naples

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).

A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.

4.93 out of 5 average rating, 120 reviews

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.

A spacious living area features a light-colored sofa paired with a round coffee table, surrounded by four accent chairs. Natural light filters through several windows, showcasing the modern decor, including framed artwork and decorative plants.

4.95 out of 5 average rating, 20 reviews

Downtown Naples Beach Condo, Off of 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 4 guests.

4.98 out of 5 average rating, 102 reviews

A screened-in pool area features a sparkling pool surrounded by a spacious deck, adorned with potted greenery. Several lounge chairs are positioned nearby, with views of lush landscaping visible through the screens. Sliding glass doors lead into the home, offering a seamless connection to indoor spaces.

Home in East Naples

Naples Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at Naples’ world-renowned beautiful beaches. The home is only 10 minutes away from downtown Naples, which features some of the very best restaurants in Florida. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. As this is our own vacation home, we’ve made every effort to make it as comfortable and convenient as possible.

5 out of 5 average rating, 7 reviews

A spacious living area features a modern open-concept design with wooden beam accents. Light-colored furniture includes a white sofa and two armchairs. A round coffee table sits in front, and a comfortable workstation is visible nearby. The kitchen is seen in the background.

Condo in East Naples

Naples Tyme Retreat

New spring rates! Enjoy Spring at Naples Tyme Retreat — an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining. Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.