Holiday rentals with outdoor seating in 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.

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!

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.

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.

Oasis Naples Condo 2BR/2Bath

Soak up the warm southwest Florida sun and enjoy a clean modern home with gorgeous views. This newly renovated condo is a short 5 minute car ride to Naples Beaches and 15 minutes to downtown. Two bedroom, two full bath home is the perfect quiet place for a couple’s retreat or for working remotely with high speed internet. The main pool IS open dawn to dusk!!! It’s a two minute walk within the community! (The smaller pool by the condo is closed and still waiting for completion.)

Sugar Beach Bungalow With a Pool!

Come jump in the pool! Put away your wool hats, hang up your parkas, and break out the swim trunks, sunglasses and flip flops. There’s no better way to celebrate summer (or escape winter) than with a relaxing beach vacation. Bring the whole family, roll with a group of friends, or make it a romantic retreat. Whatever the trip, opt for a luxurious vacation rental with all the home amenities you’re used to at home—and some. This incredible beach home has it all!

Naples' Home With Private Pool - Esthetic Stays

If you have to be isolated, do it in style. This luxurious Naples vacation home comes with our Triple-Cleaned Promise, ensuring a spotless and thoroughly disinfected environment for your peace of mind. Enjoy social distancing in comfort with your own private pool, luxurious amenities, and four complimentary bikes for exploring the area. Whether you’re relaxing outdoors or staying active, you’ll experience total comfort, confidence, and peace during your stay.

Beachside Haven | Family 3BR Near Vanderbilt Beach

We’re so excited to share our beautiful home with YOU! Located in the heart of Naples Park . Our 3-bedroom, 2-bath home is perfect for families, friends, or anyone looking for a blend of relaxation and quiet. The home is designed the home for maximum comfort and fun! The house is FULL of amenities, games for adults and kids - if you find something we don't have - message us :-) Let us host you in Naples Park, a few minutes from beautiful Vanderbilt beach.

2br/2ba spacious House near the Ocean

Welcome to our stylish and comfortable retreat, located just 1.3 miles from the sandy shores of Vanderbilt Beach and the scenic beauty of Wiggins Pass State Park. With the vibrant Mercato district nearby, you'll have access to an array of dining, shopping, and entertainment options. Our well-appointed accommodations include two bedrooms with king-sized beds, as well as a queen-sized sleeper sofa, making it perfect for families or groups of friends.

~ ~The Studio~ ~ Comfort, Quality, walk to beaches

This unique and comfortable studio is equipped with everything you might need. Walking distance to everything or you can use the beach bikes that we have for you. Myself as a Superhost ( with over 300 five-star reviews) and my team will make sure you have a memorable stay without missing anything, because we are someone who truly care for you and your stay. Let us welcome you.