Holiday rentals with outdoor seating in Old Naples

Naples Cottage for two- your own private home

Welcome to your own waterfront home on private lot close to Naples beaches! This perfect tropical cottage for two comes with a big view of a natural lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting. Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens, Pickleball courts or one of the many restaurants or art galleries close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do near you!

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

#Blocks2Beach Lower Studio Palm Villa Close2 #RITZ

Gorgeous newly renovated private one King bedroom with en-suite bathroom. This 1st floor studio has modern updates with new furniture, comfortable mattress, fluffy pillows & luxury linens. Small refrigerator, microwave & Keurig in studio for guests to use. Just BLOCKS to the best beach where the sunsets are divine at Vanderbilt Beach. Easy walk to the Ritz Carlton Naples Beach Resort with the finest ocean front dining. Enjoy beach activities including shelling, SUP, fishing, kayaking & more!

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!

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!

Sandy Cove Cottage/Sandy Cove Villa near the beach

Sandy Cove is one bedroom, one bathroom Cottage located only 10 minutes from Downtown Naples, beaches, 5th Ave, fine dining and world-class art galleries. Sandy Cove Cottage is next to the Hamilton Harbor Yacht club, & within walking distance to beautiful Naples Bay. Only a short bike ride to the Naples Botanical Gardens, Sudgen Park, & East Naples Park- Home of the Pickleball Championship! Sandy Cove Cottage is fully furnished, just bring your clothes and settle in for some fun in the sun!

Relaxing Naples Home close to beach and downtown.

Enjoy this single level "just renovated" traditional Naples home, just blocks from beautiful beaches, the Naples Zoo, Naples Preserve, the Conservancy of Southwest Florida, the Gordon River Greenway Park, Coastland Mall, and 5th Avenue's abundant restaurants and shopping. Features include 3 bedrooms (including 1 bedroom with bunk beds (double and twin), a 2 car garage, covered lanai and laundry. It is located in the Lake Park neighborhood known for its quiet charm and mature canopy trees.

Aesthetic Lush Landscape, 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. 624/34 Mbps at antique desk. SMALL quiet pets ok. Attached to owner's home but Studio is Completely Private! Only One Bed!

"The Boho Bliss" Lakeview Elegance 3miles Downtown

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.

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.

Gulfside Sleeper in the ❤ of Historic Old Naples

Bright, clean 2nd floor studio is ideal for 1 or 2 travellers. Minimalist design with an emphasis on comfort and relaxation is perfect for executive business travellers or sun seeking beachgoers. No car necessary. The small space is hard flooring of wood and tile. There is an open closet with hanging rod. The shower access is a bit tight, and may not be suitable for big and tall or plus sized individuals. The westward view from the window is one block from the beach sunsets.

Private Heated Pool | Playset | Near the Beach!

Just minutes from the beach, Flamingo Feliz is a cheerful 3-bedroom getaway with a brand-new pool, cozy tiki lounge, and family-friendly extras. Enjoy smart TVs in every room, a fully stocked kitchen, beach gear, bikes, and plenty of space to relax. The heated pool (heating avail. Oct–May) and outdoor living areas make it perfect for a sunny Florida escape. Located near 5th Ave dining, shops, and Naples' best beaches—everything you need for a laid-back vacation!