Family-friendly holiday rentals in Naples

4.96 out of 5 average rating, 114 reviews

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, 138 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!

4.96 out of 5 average rating, 192 reviews

Home in East Naples

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

4.97 out of 5 average rating, 387 reviews

Guest suite in Naples

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

4.95 out of 5 average rating, 130 reviews

LUXE Oasis | HTD Pool |10 min Beach +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!

Apartment in South Naples

4.95 out of 5 average rating, 161 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. We do not offer snorkeling gear.

4.98 out of 5 average rating, 260 reviews

Flat in Naples

Bear Necessities - 1 Bdrm 1 Bthrm w/Kitchen/Lvrm

Relax and enjoy Florida indoors and outdoors in this "mini-apartment". You can watch for roaming wildlife and enjoy the tall pine trees, palm trees, and cypress trees from the patio. The "mini-apartment" is within walking distance of the canal where you can go bird watching and possibly see other wildlife. The apartment is outside of the busy hustle and bustle of the city but within driving distance of the beach. There are several restaurants with indoor or outdoor dining options.

4.96 out of 5 average rating, 110 reviews

Home in Naples Park

The Beach Getaway Home only steps from the water!

Perfect location for a beach getaway! Centrally located, enjoy all of Naples in the Naples Park neighborhood. Less than half a mile from Vanderbilt beach, walk or bike to the sunny gulf coast in under 10 minutes. Also steps away from the Ritz Carlton tiki bar! Shop groceries at the nearby Whole Foods, Trader Joes, and Publix. Feel like an evening out that's close by? Enjoy the Mercato shopping and dining area with several bars, restaurants, nightclubs, and even a movie theater.

4.93 out of 5 average rating, 122 reviews

La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

4.9 out of 5 average rating, 105 reviews

Home in Naples Park

699 Gulf Breeze Oasis · NEW Heated pool w Sundeck

Welcome to 699 Gulf Breeze Oasis! Come in and stay in our fully remodeled, contemporary vacation home or relax in our NEW heated pool! Featuring a gorgeous, waterfall fountain & sun deck surrounded by lush tropical foliage. 699 Gulf Breeze Oasis is your bound to be your newest, completely private vacation home! Located just a mile to world class, white sand beaches, waterfront dining, live entertainment and open air shopping! We look forward to hosting you!

4.98 out of 5 average rating, 131 reviews

Home in East Naples

Pool Home! Near Beach, Walk to Coffee & Dining!

Your Perfect Naples Getaway! This modern 3-bed, 2.5-bath pool home offers the perfect mix of comfort and convenience. Just 4 miles from Naples Beach and Downtown 5th Ave, you'll be close to world-class shopping, dining, and entertainment. Enjoy a walkable neighborhood with restaurants, a coffee house, a brewery, and fishing nearby. After a day of exploring, relax by your private pool and soak in the Naples lifestyle!