Family-friendly holiday rentals in Naples

Boaters Bayshore Bungalow w/HOT TUB view of water.

BRING YOUR BOAT! This ranch home is located on a canal with direct access to the Gulf/Naples Bay(no bridges). Amazing water sports access. In the cool/hip Bayshore Arts district! Great restaurants, Naples Botanical Gardens, boating, 3 miles to DT Naples and 4 to the best beaches. This is a perfect family/friends vacation spot. We have all the gear to enjoy this location. Quiet neighborhood/newly renovated/great views. Coffee on the deck with sunrise in front of you or drinks at sunset. Serenity

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.

#Blocks2Beach Lower Studio Palm Villa Close2 #RITZ

Gorgeous newly renovated private one King bedroom with en-suite bathroom. This 1st floor studio has modern updates with new furniture, comfortable mattress, fluffy pillows & luxury linens. Small refrigerator, microwave & Keurig in studio for guests to use. Just BLOCKS to the best beach where the sunsets are divine at Vanderbilt Beach. Easy walk to the Ritz Carlton Naples Beach Resort with the finest ocean front dining. Enjoy beach activities including shelling, SUP, fishing, kayaking & more!

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!

By the Beach and 5th - Studio Apartment with Pool

Great location! Newly renovated! A studio guest apartment with your own private entrance, full kitchen & bath! A non-smoking home only 1 mile from the beach, 5th Ave dining & 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 there's also a pool? Or that you can sing along to your fave tunes in the shower via a Bluetooth speaker? This home is 325 square feet of clean cuteness!

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

Garden House-2 Bedroom/2 Bath-Naples / Park Shore

WHOLE HOUSE RENTAL-Intimate quiet setting. 2 miles from the beach and 4 miles from (a 10 minute drive) Downtown / 5th Avenue Naples. The house is within easy walking distance of the Park Shore Area / US41 / Tamiami Trail restaurants and bars. Outdoor hot tub, fire-pit and lush green gardens for a tranquil stay. There are no hidden cleaning fees on this listing which is a huge plus. There are also no hidden cameras or sensors of any kind at the house—your privacy is respected.

Pool Bikes & Beach | Paddle Board Included

We welcome your family of up to 2 adults & 3 children. You will be close to sandy beaches, great restaurants and shopping at this great North Naples Location. Just a few minutes from Vanderbilt Beach and Wiggins Pass Park. You will love all the great amenities and be able to relax in this brand new clean apartment. Amenities, Bikes, paddle board, beach wagon and beach towels. Very easy to check-in, you will have your own private entrance and private one car parking available.

Royal Palm flat Bay side shoppes

Royal Palm flat first floor charming Just remolded, updated new on market fresh, with large back porch and shared garage with beach toys, close to the beach 1 block from 5th Ave. one mile from beach 3 blocks from Naples bay. close to many restaurants and shops on 5th ave. The beach is at the end of 5th Ave. great walk down the heart of Naples down town and charming tin city shops and dinning. view 5th ave from rear porch. entire first floor with many games in garage.

Private Heated Pool | Playset | Near the Beach!

Just minutes from the beach, Flamingo Feliz is a cheerful 3-bedroom getaway with a brand-new pool, cozy tiki lounge, and family-friendly extras. Enjoy smart TVs in every room, a fully stocked kitchen, beach gear, bikes, and plenty of space to relax. The heated pool (heating avail. Oct–May) and outdoor living areas make it perfect for a sunny Florida escape. Located near 5th Ave dining, shops, and Naples' best beaches—everything you need for a laid-back vacation!

Jony’s Paradise

Only 1 parking available 1 Room- Kitchen- Bathroom located 3 miles from Beach and Downtown Naples with private entrance and free parking. 350 sqft Do not to bring AC bellow 20* 70* because it might get frozen Turn off AC before getting out since it might be frozen once you get back Please do not trow paper towels or anything into the toilet. No smoking Thanks

Las Casitas in Naples # 3

Welcome to your home away from home! Beautifully renovated condo, located close to shops, restaurant, and the beach. This condo is located at the edge of a natural preserve; giving you the best of both worlds: you can sit in the backyard and enjoy a quiet and relaxing afternoon, or take a short walk and find yourself at local restaurants, the beach, wine bars, or shops.