Holiday rentals with outdoor seating in Old 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

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 | 10 min Beach and 5th Ave•HTD Pool•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).

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!

Waterfront ocean access canal, Kayaks, Bikes Beach

We renovated a key west style home into a modern beachy oasis. You can kayak, bike and boat to the beach right from the house! This safe waterfront neighborhood has tons of friendly people out walking, running, biking, dog walking, etc. The house is 1/4 mile to the beach as the crow flys. Beach entrances are 2 miles away. We have 2 nice adult bicycles, kayaks and fishing rods for you to use. Located just off Wiggins Pass Road between 41 and the ocean. Stilt home. Don’t even need a car.

Attention Naples Lovers! Entire Home w/Pool&HotTub

Enjoy the heart of Naples from a modern vacation home located in a quiet, safe neighborhood with a private hot tub, heated pool, and screened patio. Stay in and have a wine night in the stunning, open-space kitchen island or go out and enjoy the many fine dining and beautiful beach views that Naples has to offer - minutes away! The home is newly renovated with new appliances, new furniture, a new hot tub, and a heated pool to savor Florida right in your own fully fenced private backyard.

Downtown Naples Beach Condo, Off of Famous 5th Ave

This peaceful Olde Naples condo is just half a block from dining and shops on famous Downtown 5th Ave and 4 blocks from Naples Beach. This first-floor end-unit condo is perfect for a beach getaway. This clean, modern unit has a pool just feet from the front door, a complete kitchen with updated appliances, a new washer and dryer, comfy furniture, beach chairs and umbrella, and high-speed internet. This property offers a perfect blend of relaxation and convenience to sleep up to 4 guests.

"The Boho Bliss" - Reset & Recharge Wellness House

Discover Bohemian Bliss in this uniquely styled home, 2mins walk to Sudgen Lake in Naples that includes beach, lake activities, walking trails or biking. Vibrant energy with the comfort of your creatively adorned space that tells you a story. All brand new, high-quality furniture, Tempur-Pedic mattress, Very Fast WiFi, King-size bed, TVs in all bedrooms, fully equipped kitchen, Fire pit, BBQ. Reserve now so we can welcome you home, to a boho-inspired sanctuary in the heart of Naples.

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!

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.

Emerald Palm Villa, 2 bed / 2 bath with pool

Welcome to your dream getaway - short drive from the world-renowned 5th Avenue and the pristine white-sand beaches of Naples. This stylish 2-bedroom pool home is the ideal blend of relaxed coastal living and upscale comfort. Whether you're seeking relaxation, adventure, or a little of both, this Naples retreat has everything you need for a truly unforgettable vacation.