Family-friendly holiday rentals in Old Naples

Backyard Oasis - Large heated pool/Wi-fi/Lanai/PS3

Enjoy a great vacation in our beautiful Naples home. With three spacious bedrooms, modern decor, plentiful natural light, and a full kitchen, this upscale home is perfect for groups of friends or families seeking a sunny getaway. Enjoy direct access to a private pool and an ideal location in a safe neighborhood just a short drive from stunning beaches. 8 Min Drive to 3rd Avenue 10 Min Drive to Naples Botanical Garden 12 Min Drive to Naples Pier and Beach Experience Naples With Us & Learn More

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.

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!

Relaxing Naples Home close to beach and downtown.

Enjoy this single level "just renovated" traditional Naples home, just blocks from beautiful beaches, the Naples Zoo, Naples Preserve, the Conservancy of Southwest Florida, the Gordon River Greenway Park, Coastland Mall, and 5th Avenue's abundant restaurants and shopping. Features include 3 bedrooms (including 1 bedroom with bunk beds (double and twin), a 2 car garage, covered lanai and laundry. It is located in the Lake Park neighborhood known for its quiet charm and mature canopy trees.

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.

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!

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.

Beach & Pool Escape – Walk to Naples Hotspots

Modern 3BR/2.5BA Naples home with private pool, perfect for adults seeking comfort and fun. Sleeps 6 with king suite, queen room, and queen-over-queen bunks. Relax poolside or head to the beach with provided chairs, umbrellas, blankets, and coolers. Walk to Botanical Garden, breweries, and dining. High-speed WiFi, Smart TVs, and desks keep you connected if needed. Kid-ready with Pack ’n Play, high chair, and toys.

Sunside House, 3/2 Pool Home in Gated Community

Prepare to be impressed as you enter this beautiful home in the sought-after Community of Briarwood. It certainly has the 'WOW' factor. The open aspect of this great-room floor plan, which flows out to a large, very private SW facing Patio and Pool area, makes this a perfect home for entertaining, family time or your golf time. You will love how light, bright and spotless this gorgeous home is. So much NEW.