Family-friendly holiday rentals in Old Naples

Boater’s Paradise-Stunning Sunsets! Games Room!

Newly renovated! This 3 bed/4 bath home is on the nicest canal with 200+ ft of frontage & gorgeous views of the canal & sunset. The pool, tiki hut & docks have full sun all day. Each bedroom has a private bath & there's a 2 pc powder room off the laundry. The primary has a king bed & walkout to pool. The 2nd bedroom has a queen bed & pool access. Bedroom 3 has a queen & private bath. Fully equipped kitchen with everything you need. And a games room! Enjoy the stunning sunsets on the water!

LUXE: Beach Home w/ Screened Pool & Spa, BBQ

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.

Beach Last Minute Spring Specials Hot Tub Pets OK!

Fresh and clean, two bedroom, sunroom, two bathroom, furnished vacation rental, fenced yard, hot tub, pet friendly! Just a mile walk, bikeride or shuttle to Beach. Close to everything, Ritz Carlton, Mercado Shopping, Theater, Fitness, Pubs, Bike-Boat-Paddle Board-Kayak Rentals, Museums, Whole Foods, Restaurants, Nightclubs, Golf Courses, Coffee Shops, Library, Marina, Parks, Pickle Ball, Cycling, beautiful, Wiggins State Park and a short drive to Everglades National Park and Airboat Rides.

Ft. Myers Quaint Getaway! Minutes from Beach!

My condo is close to the beach, nightlife, public transport, and family-friendly activities. It is good for couples, solo adventurers, business travelers, and families (with kids). It's minutes from Ft. Myers and Sanibel Beach. It has a King size bed in the master bedroom and two twin murphy beds in the guest room. Walking distance from a Super Target and trolley. Several outlet malls, closest is 2 miles. FYI, not handicap accessible (second floor unit). A few steps to the pool and grill.

Sanibel Romantic Getaway

Sanibel; named by Travel & Leisure as one of the top 50 “Best Places” internationally to visit in 2025, with its restaurants, shops and of course, Sanibel’s incredible beaches, rebuilt and open for business. Fully equipped kitchen, sheets, towels, etc included. Great restaurants and shopping, lighthouse and parks. Bike rentals and trails throughout the island allow you to access all the hidden treasures on Sanibel. A 2 minute walk to access our pristine white beaches .

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 renovated 2 bedroom, 2 bath with washer and dryer. This modern top floor unit with elevator gives you a breath-taking view over this beautiful resort which offers heated pool, tennis, pickleball, poolside ocean to table restaurant Hogfish Harry's. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

Charming cottage bay area

Key west style stilt home Newly remodeled 2018, offering entire first floor bungalow, my place is 2 blocks to 5th Ave district, restaurants and dining, the beach is about 1 mile west, family-friendly activities, nightlife. close in, the location Naples Bay area. tin city -and bay front shops are 4 blocks west . roll away bed available if needed in garage. many beach toys available in garage. coolers beach towels everything you can think of.

Lovers Key Beach Club Suite

Enjoy breathtaking views from this 10th floor condo at Lover's Key Beach Club! This one bedroom, one bath condo is the perfect place for a quiet, romantic couples getaway. From the private beach to the large pool area, there's no better place to relax in the Florida sunshine! Wake up refreshed and sip your coffee on the private balcony overlooking the water. Prepare meals in the full kitchen or head down to the BBQ grill area!

Cosy Cottage luxury kitchen

Charm meets history in this cozy cottage! Original beams crown a luxury kitchen (marble floors, granite counters!), while exotic fruit trees whisper secrets in the fenced backyard. Sun-drenched patio w/BBQ awaits soirées. Just 1.4 miles from the beach & vibrant shops/restaurants, all footsteps away. Classic Spanish arched gates promise enchantment within.