Vacation rentals in Naples Bay

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Top-rated vacation rentals in Naples Bay

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Top guest favorite

A spacious deck extends over the canal, surrounded by lush palm trees. Comfortable seating is arranged around a fire pit, with a paddleboard propped nearby. A BBQ grill is visible, inviting outdoor dining in a serene waterfront setting.

Home in East 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

4.94 out of 5 average rating, 164 reviews

Top guest favorite

The image showcases a bright, inviting pool area featuring clear blue water illuminated by string lights above, creating a relaxed atmosphere. Surrounding spaces include a cozy living room with comfortable seating and a spacious kitchen area with modern fixtures and finishes.

Home in East Naples

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).

4.96 out of 5 average rating, 156 reviews

Top guest favorite

A spacious living area is highlighted by a light-colored sofa adorned with turquoise cushions. An elegant chandelier hangs from the ceiling, complementing the large wall-mounted TV. Natural light fills the room through windows, with a dining area visible in the background.

Home in Naples

Beach, Sun and Fun! *Beach House * New Listing

Location! Location! Location! 3 beautiful bedrooms, 2 baths, just 1 mile to the beach and entertainment. Peaceful and private, this home boasts an abundance of room for entertaining and outdoor space, free parking and access to private beach. Conveniently located close to the Venetian Village, Water Side mall and 5th Avenue which futures several casual and upscale dinning, shopping and multiple entertainment venues. Great for a relaxing vacation and enjoying the Florida sunshine and sunsets!

4.97 out of 5 average rating, 107 reviews

Top guest favorite

Home in East Naples

Cozy and Stylish, 2 King, Close to Beach & 5th Ave

Nestled on a tranquil street in the heart of Naples, this newly renovated retreat offers the perfect mix of modern comfort and coastal charm. Step outside to a chic outdoor living area, perfect for enjoying your morning coffee or relaxing in the evening breeze. Just minutes from renowned 5th Avenue and pristine beaches, it's easy to enjoy the best of the area. Plus, we provide all the beach essentials — chairs, umbrellas, and towels — so you can fully relax and enjoy the sun-soaked paradise.

4.97 out of 5 average rating, 58 reviews

Top guest favorite

A private, landscaped patio features two swivel chairs positioned around a small table. Lush greenery and flowering plants surround the area, providing a serene view of a lake in the background. The natural setting invites relaxation and enjoyment of the outdoors.

Condo in Old Naples

Little Gem By the Beach and 5th w/Patio Old Naples

JUST A SHORT WALK TO THE BEACH AND 5th AVE, IN THE HEART OF OLD NAPLES, WITH A RARE, PRIVATE PATIO! Totally renovated in January 2023! A beautiful, one-bedroom, one-bath home, with only a 5-minute stroll to the beach and dining! Just outside the living room is a private, landscaped patio overlooking a pretty lake, which is an unusual and lovely feature of this home! Inside, you'll enjoy a fully-equipped kitchen with granite countertops, a comfortable king bed, and washer/dryer in the condo.

5.0 out of 5 average rating, 91 reviews

Top guest favorite

A spacious living area features a light-colored sofa paired with a minimalist side table. A dining table with chairs is positioned near the kitchen area. Natural light fills the room through large windows, highlighting the natural wood ceiling and creating an open atmosphere.

Home in East Naples

Your Perfect Naples Getaway

Unbeatable location near Downtown Naples, 5th Ave, Tin City, and just a short bike ride to Naples Pier and Baker Park! This newly renovated 1-bedroom, 1-bath unit with a Queen pull-out couch combines comfort and convenience in a private duplex. Relax on the screened porch, enjoy lush tropical surroundings, and grill on the paver patio. Complete with a private washer/dryer, it's perfect for couples or groups—each unit sleeps 4. Stay close to world-class golf, dining, shopping, and more!

5.0 out of 5 average rating, 41 reviews

Top guest favorite

The image captures a view of a sandy beach leading to a pier extending into the ocean. Waves can be seen crashing against the pier, while green foliage frames the foreground, enhancing the natural coastal scenery under a clear blue sky.

Condo in Old Naples

Fun At The Beach

2024 Beautifully Remodeled Unit! Located 1 block from Naples Pier (rebuilding currently) and 3rd Ave Dining and Shopping. Private entrance to unit with designated parking. The pool is outside your door for easy access. The unit provides a master suite with a king and the extra room has 2 twins that can convert into a king. Please request upon booking. A laundry facility is located on the premises. Kitchenette provides cooktop and microwave/convection oven & a small refrigerator.

4.98 out of 5 average rating, 129 reviews

Top guest favorite

Apartment in East Naples

Resort at Bayshore Arts District • 5th ave & Beach

Stay in a private resort-style studio just 8–10 minutes from Downtown Naples & 5th Ave and 10–12 minutes to the beach 🌴 Located in the vibrant Bayshore area, you’ll be minutes from Celebration Park, the Naples Botanical Garden, nearby pickleball courts, and Paradise Sports Complex—perfect for events and youth tournaments. 10–15 minutes to NCH Baker Hospital and Physicians Regional. The space features a king-size bed, open layout, private terrace, and a clean, modern design.

5.0 out of 5 average rating, 14 reviews

Top guest favorite

Home in East Naples

" Velvet Bloom” Bubbling Spa Retreat with Sauna

Deep-hued velvet furnishings create a luxurious ambiance at the Velvet Bloom. Only 3.5 miles from Downtown and the beach. 2mins walk to Sudgen Park Lake which includes kayaking, beach, walking trails & biking. All brand new, high-quality comfortable furniture, Tempur-Pedic mattress, Very Fast WiFi, King-size bed, TVs in all bedrooms, fully equipped kitchen, Fire pit, BBQ, bikes, and much more to offer. Reserve " Velvet Bloom " for exquisite lakefront experience.

5.0 out of 5 average rating, 108 reviews

Guest favorite

Home in East Naples

Pet Friendly | Screened Porch & Private Yard

Charming Florida home tucked in the heart of Naples. 1790 Smugglers Cove features a private screened porch with string lights, a sunny backyard patio, and bright coastal-inspired interiors, the perfect home base for your Naples getaway. All within 2 miles of: Naples Beach & Pier — sunbathing & sunsets 5th Avenue South — upscale dining & shopping Boat tours, kayaking & water sports Tin City along the Gordon River Message us for local recommendations!

5.0 out of 5 average rating, 11 reviews

Top guest favorite

Condo in East Naples

Naples Luxurious Resort Retreat with Lazy River

Naples Tyme Retreat is an elegant, newly renovated, 2-bedroom, 2-bath condo that sleeps 6. Enjoy luxurious resort amenities, including 5 pools, a spa, gym, tennis, and world-class dining (see below for resort fees). Just steps from vibrant 5th Avenue and Naples' stunning beaches, this serene retreat offers a private lanai, modern kitchen, and sophisticated decor. Perfect for families or mature travelers seeking a blend of relaxation and upscale living.

5.0 out of 5 average rating, 30 reviews

Top guest favorite

A spacious living area features a large sectional sofa in neutral tones, paired with accent pillows. A coffee table sits on a textured rug, while plants add a touch of greenery. Natural light floods in through expansive glass doors that open to a private outdoor space.

Home in Naples

3 Bedroom Waterfront Getaway in Downtown Naples!

Your family will be close to everything when you stay at this centrally-located condo in Downtown Naples! Enjoy your morning Coffee out on your private deck overlooking the canal that takes your directly out to Naples Bay & the Gulf! Space to dock your boat as well. This 3 bedroom/3bathroom condo will transform your stay into a peaceful retreat, conveniently only minutes from 5th Avenue, the beach, & restaurants! What more can you ask for?!

4.93 out of 5 average rating, 68 reviews