Family-friendly holiday rentals in Old Naples

Pool House+Game Room, Moments to Beach & Downtown

Welcome to our Happy Place! This fully renovated Naples retreat sleeps 6 and blends modern comfort with family fun. Enjoy a bright open-plan living area, chef’s kitchen, and 3 bedrooms including a master with pool access. Step outside to your private screened oasis with heated pool, lounge seating, grill, canal and golf course views. The garage game room offers ping-pong foosball & arcade basketball. Just minutes to beaches, dining, and downtown, it’s the perfect getaway for relaxation and play.

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

Lux Oasis | HTD Pool•10 min Beach and 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!

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).

Downtown Condo at Naples Pier Beach

Come enjoy a restful beach escape at the Naples Mariner, formerly a beautiful Motel built in 1966! Relax while enjoying your fully renovated condo located 60 yards from the Olde Naples Fishing Pier beach and 1 block from the 3rd Street Shops/Restaurants. A quick drive, bike or walk 1 mile north will place you on 5th Avenue - an area of shops, restaurants, bars and a playhouse. The condo has one designated parking spot, wifi, washer/dryer on premises, heated pool, courtyard & more. 'Sea' Ya!

Beach, Sun and Fun! *Beach House * New Listing

Location! Location! Location! 3 beautiful bedrooms, 2 baths, just 1 mile to the beach and entertainment. Peaceful and private, this home boasts an abundance of room for entertaining and outdoor space, free parking and access to private beach. Conveniently located close to the Venetian Village, Water Side mall and 5th Avenue which futures several casual and upscale dinning, shopping and multiple entertainment venues. Great for a relaxing vacation and enjoying the Florida sunshine and sunsets!

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.

Rare Gem, Fast WiFi, 3 Min to Town, King Bed

For Guests Who Love Privacy! Sunny Studio where Art is highlighted. French Doors to Lg Screened Porch for Outside Dining/Working. Peaceful. Stilt home (8 steps) in Safe, Quiet area w parking right outside. Backyard is yours w BBQ grill, table & chairs. Charmingly Furnished w Recliner, Heavenly King Bed, Convection/Microwave oven, Kitchen Aid stove top & Full Fridge. FAST WiFi at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

Fun At The Beach

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier (rebuilding currently) and 3rd Ave 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 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 refrigerator.

75"TV, World Tennis Club, Beach 4ml, Sauna, HotTub

🌐 Guests recognize us as Catch of Naples — read the reviews and see why active travelers choose us! ✨ Introducing Catch of Naples ✨ 🎾 Stay active at Blue Coral Naples Coastal Home in WTC – with 16 tennis & 4 pickleball courts, 2 pools, hot tub & sauna right in the community! 🏖️ Just 4 miles to Naples beaches & 10 min to downtown dining. 🚲 Bikes, beach chairs & umbrellas included for endless outdoor fun. 🌴 Relax on the lanai while kids play safely in our gated community.

Private Pool · 4 mi to Beach · Walk to Dining

Private Naples pool home with direct pool access from the main bedroom and living area. Beach in the morning, your own open-air pool in the afternoon, then walk to dining, coffee, breweries, and Celebration Park food trucks and live music. Four miles to Gulf beaches, 5th Avenue South, and downtown. Sleeps 6 comfortably, (up to 7 total with added fee), all on one level. BBQ grill, beach gear, Smart TVs, Pack ’n Play, high chair, and possible boat/trailer parking.

4BR Near Downtown Naples, Beach, Bikes, BBQ& Games

Relax in this spacious 4-bedroom Naples home minutes from the beach, 5th Ave shopping, and downtown dining. Ideal for families and groups, this 1,864 sq ft retreat offers king beds, bikes, beach gear for 8, outdoor games, BBQ, and two outdoor lounge areas everything needed for an easy Southwest Florida getaway. We have stellar reviews, come check us out & see for yourself. ⭐ Consistently 5-star rated | Superhost owned & operated