Holiday rentals with outdoor seating in Old Naples

4.96 out of 5 average rating, 109 reviews

Home in South Naples

New Home, 6 Beds, Heated POOL / Game Room

Park in the driveway and enter through the front double doors to a newly and completely updated Home with 3bedrooms and 3 full bathrooms located just 7 miles from the trendy 5th avenue south, white sanded beaches and the famous Naples pier; This private and MODERN exquisite home has everything you need to enjoy an endless summer alike stay. Heat for the Pool Available EXTRA $ October to May $40 EXTRA per each night stay May to September $30 EXTRA per each night stay. Game Room and and Gym area.

4.94 out of 5 average rating, 123 reviews

LUXE Oasis | 10 min Beach+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!

4.96 out of 5 average rating, 188 reviews

Home in East Naples

Serene Home 10 min 2 Beach w/ Bikes & Master Suite

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

4.99 out of 5 average rating, 119 reviews

Holiday home in Naples

25% OFF · Beach 3mi · 2 Htd Pools · Tennis · Pickle Ball · Bikes

Play TENNIS (16 courts) and PICKLEBALL (4 courts). Free clinics. World Tennis Club encompasses 82.6 acres. About 6 mls to downtown and 3 mls to the beaches. Redesigned 2 bdrs 2 baths condo in WTC Resort, designed for up to 6 guests. The largest layout in this subdivision at the FIRST-floor unit also has 2 huge lanais. The living room features sectional sofa and 75 inches flat screen Smart TV with internet and cable fiber optic speed of 250. Another TV is in the master. Safe GATED community.

4.96 out of 5 average rating, 109 reviews

Apartment in East Naples

Beaches & 5th Ave 2.5 miles away!

Bring your family and friends to our Southwest Florida paradise! This stylish space is the newest addition to our profile. Located in Naples Florida and within a 7 min drive to 5th Ave shops, restaurants, and beaches. Enjoy a 10 min walk to Celebration Park and local restaurants. Guests can enjoy this newly remodeled condo that has everything you will need for your Naples getaway. **If you have a larger party, inquire and view our profile about the 3 other condos on this property.

4.98 out of 5 average rating, 101 reviews

Home in East Naples

Naples Retreat: Heated Pool - Minutes to Beach

We know that you’ll love it here – whether you spend your time lounging by our pool, or at Naples’ world-renowned beautiful beaches. The home is only 10 minutes away from downtown Naples, which features some of the very best restaurants in Florida. If dining-in is more your thing, you will have a fully stocked kitchen with every amenity you could wish for. As this is our own vacation home, we’ve made every effort to make it as comfortable and convenient as possible.

Apartment in South Naples

4.95 out of 5 average rating, 155 reviews

Sea Shell Villa 1

Your will be close to everything when you stay at this centrally-located villa. Our villa is fully upgraded. Has a full kitchen, 1 bedroom with a queen bed and laundry room with a full size washer and dryer. There is a great variety of restaurants and shopping just minutes away. In just 15 minutes you can be at the famous Naples pier for a fun day at the beach. We also have Marco Island, which is one of the top beaches in the world, just 20 minutes away.

4.96 out of 5 average rating, 107 reviews

Tropical paradise 5 minutes from the beach

Come on in and unwind in this peaceful and one-of-a-kind oasis just a short 5-minute drive from Wiggins Pass beach! Feeling adventurous? Hop on a bike and you'll be there in a little over 15 minutes. Located in North Naples, this charming house is fully stocked with everything you need to cook, discover, unwind, and rejuvenate, this space even boasts its own private backyard. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

Superhost

Guest house in Naples

4.81 out of 5 average rating, 148 reviews

Coastal Cabana - 2 Miles to Beach and 5th Ave

The Coastal Cabana is an adorable one-bedroom guest house less than two miles to the beach and the best shopping and dining in Naples. This downtown location in the 34102 zip is unmatched when it comes to beach accessibility and the best of everything downtown Naples has to offer. The Cabana is tucked away in a small, quiet coastal neighborhood walking distance to the Naples Zoo and Conservancy of Southwest Florida, and Gordon River Greenway!

4.94 out of 5 average rating, 102 reviews

Private Oasis in the ♥ of Naples ☀Heated Pool/Spa☀

Escape to The Private Oasis in the heart of Naples! → Welcome to 2,279 square feet of modern and elegant furnishings → Minutes to 5th Avenue, Tin City, Beach, Zoo, and Pier → Fully equipped kitchen fit for the chef at heart → Dine and unwind poolside in the enclosed lanai → Take a dip in the heated pool and spa → Grill masters will love the outdoor kitchen & bluetooth speakers → Click the ❤ to add listing to wishlist!

4.92 out of 5 average rating, 222 reviews

Home in East Naples

" The Bohemian Heaven " w/ SPA, 2miles to downtown

Welcome to the unique Bohemian Paradise. Completely renovated spectacular bright space, high-end furniture, a fantastic huge outdoor area, firepit, outdoor dining table, and BBQ station. Minutes away from restaurants and convenient stores, as well as historical Naples Pier, Naples beach, and 5th Ave/Downtown. You don't want to miss this experience.