Holiday rentals with outdoor seating in Collier County

4.95 out of 5 average rating, 106 reviews

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

4.99 out of 5 average rating, 252 reviews

Tiny home in Naples

BIG Memories TINYHouse Pickleball Ct Mile to Beach

Located less than one mile from the beach in the center of the city hustle, step inside our “Tiny House" and ease into beach life! Sailor’s knot rope tied around anchored cleats create a banister railing to a 5’6” loft bedroom nestled above a 6’2” full kitchen and bath with Surfboard Shower. The 12' living room makes the 360 sq ft space feel more expansive. The new construction is separated from the main house by a breezeway. The private entrance and courtyard was designed for absolute privacy.

4.95 out of 5 average rating, 132 reviews

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!

Cottage in Everglades City

4.98 out of 5 average rating, 163 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

4.95 out of 5 average rating, 156 reviews

Private Paradise | Large, Peaceful Studio w Patio

This modern coastal retreat is a complete studio apartment with a direct, private entrance: Private outdoor sitting area w/ umbrella Smart TV w/ Netflix, Amazon TV, Disney+ Queen sized bed w luxury mattress Dresser & closet Workspace w/ wireless charging Walk-in marble tiled shower w/ full vanity Incl. Bath Amenities Kitchenette w/ fridge & freezer Keurig w/ complimentary coffee Induction cooktop Microwave Toaster Oven/Air Fryer Washer/Dryer Beach Towels, Chairs, Umbrella Parking for one car

4.95 out of 5 average rating, 162 reviews

Apartment in Naples

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. We do not offer snorkeling gear.

4.95 out of 5 average rating, 129 reviews

Lovely Beach Bungalow pool/spa 1.5 mile bch Naples

Lovely Pool/Spa bungalow, located in Naples Park, 1.5 miles from Vanderbilt Beach. Across the street from Marcato shopping center, Whole Foods, Cinema, restaurants and clubs. The unit is in pristine shape and features elegant furnishings and decor, tile floors throughout, granite counters in the kitchen, stainless steel appliances, impact windows and all white linens. Private screened in patio at the front and shared backyard area with pool/spa and BBQ. King Bed and Queen Sleeper Sofa.

4.98 out of 5 average rating, 266 reviews

Flat in Naples

Bear Necessities - 1 Bdrm 1 Bthrm w/Kitchen/Lvrm

Relax and enjoy Florida indoors and outdoors in this "mini-apartment". You can watch for roaming wildlife and enjoy the tall pine trees, palm trees, and cypress trees from the patio. The "mini-apartment" is within walking distance of the canal where you can go bird watching and possibly see other wildlife. The apartment is outside of the busy hustle and bustle of the city but within driving distance of the beach. There are several restaurants with indoor or outdoor dining options.

4.96 out of 5 average rating, 121 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 facing the preserve. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

4.94 out of 5 average rating, 132 reviews

La Dolce Vita

Escape to our charming single-family home, where comfort meets luxury in a serene setting. This delightful retreat features three spacious bedrooms, perfect for families or groups seeking a relaxing vacation. Step outside to discover your private oasis: an inground heated pool complete with a rejuvenating hot tub, ideal for unwinding after a day of exploration, enjoy al fresco dining, with ample seating to savor meals together while soaking in the beautiful Florida sunsets.

4.91 out of 5 average rating, 126 reviews

Guest house in Naples

Turtle Bungalow

Wake up to a chorus of singing birds under the splendid South Florida weather. Brew a coffee in the privacy of your bungalow, and get ready to seize the day. After a fun day at the beach or a productive working session, Turtle Bungalow will be perfect for the relaxation you need. Sit outside and enjoy the peaceful backyard view, pool, and the sweet afternoon breeze. The sun is warm, flowers are blooming… I wouldn’t wait.