Waterfront holiday rentals in Old Naples

4.96 out of 5 average rating, 114 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.

5 out of 5 average rating, 26 reviews

Luxurious condo steps to beach with heated pool!

Relax Off 5th is a 1 BR beach rental condo in the heart of Old Naples, FL, and is perfectly situated a 1/2 block off famous 5th Avenue lined with restaurants and shops and 4 short blocks to the beach. The condo is located in a charming "Old Florida" building surrounded by multi-million dollar estates with a heated pool in the courtyard. The unit is equipped with high speed wifi and has a dedicated work space and desk in the unit. There is a wifi enabled keypad to ensure simple contactless entry!

5 out of 5 average rating, 8 reviews

Flat in East Naples

Chic resort, 4 pools, walk to 5th Ave Restaurants!

Welcome to Naples finest gated downtown resort, rewarding guests with a measure of privacy and serenity. The resort features an amenity rich environment with marina, waterfront dining and shopping, Euro-style spa, an expansive activity center, three crystal-blue resort pools, multiple hot tubs, meandering lazy river and a complete fitness center. Walk to downtown 5th ave or take the complimentary shuttle to beaches or 5th Ave HAVE A LARGER GROUP? - ASK ABOUT ADDING ANOTHER UNIT TO YOUR BOOKING

4.91 out of 5 average rating, 22 reviews

Downtown Marina Retreat

Welcome to our flawlessly remolded condo in Naples, FL, featuring a king and queen bed both with en-suites. With a perfect view of the marina you'll feel like you're in paradise. Located just 2 blocks from 5th Ave and less than a mile from the beach, it's the ideal place for a relaxing getaway. The downstairs suite offers a serene peaceful view and coffee maker and microwave. Our unit includes a wine refrigerator, covered parking, pool/spa washer/dryer, tandem bike, pickleball paddles, and more!

4.91 out of 5 average rating, 160 reviews

Apartment in Park Shore

Park Shore Resort Top Floor 2 Bed 2 Bath Sleeps 6

You have found THE BEST condominium in Naples! This wonderful and tranquil get-away is set in a tropical paradise in the heart of Park Shore. A modern 2 bedroom, 2 bath with one king bed, two twin beds and one sofa bed, sleeps 6 people. This top floor unit with elevator gives you a breath-taking view over a beautiful resort which offers heated pool, tennis, pickleball, and poolside restaurant Hogfish Harry. The beach is only a mile away! Let us welcome you to your own personal piece of paradise!

4.97 out of 5 average rating, 385 reviews

Guest suite in Naples

Tropical Garden Studio Cottage (2 miles to beach)

Studio beach cottage experience in North Naples. Take one of the two complementary bicycles on an easy 15 min bike ride to the beautiful Wiggins Pass State Park or Vanderbilt beach. Just 3 miles from the popular Mercado shops, restaurants and theater. Prefer to walk? It's less than 10 mins walking to multiple great restaurants, grocery stores, and even paddle board/boat rentals, fishing trips, dolphin eco sunset & tours. Feeling adventurous? Take one of double kayaks from the dock to the beach.

4.95 out of 5 average rating, 155 reviews

Home in East Naples

Tropical Cottage by the Sea- your own private home

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

Superhost

4.86 out of 5 average rating, 14 reviews

Perfectly-Located Studio at Naples Beach & Town!

**NEW LISTING: Newly renovated & re-opened Dec 2023** Experience the best of downtown Old Naples from the comfort of this beautifully renovated studio condo! Located just steps from the beach and 3rd Street, this vacation rental is the ideal home base for your Naples retreat. Swim in the heated community pool. Check out a local boutique or head to a nearby golf course. Finish your day with a tasty meal at a top-notch restaurant on 3rd St or 5th Ave just a short walk away. Soak up the sun!

4.99 out of 5 average rating, 158 reviews

Home in Naples

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.

4.95 out of 5 average rating, 111 reviews

Apartment in East Naples

2.5 miles to Beaches & 5th Ave

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.

4.9 out of 5 average rating, 21 reviews

SoCe Flats 210 - Modern Loft Condo West Facing

The 1-bedroom, 2-bath duplex floor plan has ceiling to floor west facing windows spanning two levels and offers the largest under air square footage in the building. SoCe Flats is an exciting new condominium development in the most desirable neighborhood in Naples, the Paradise Coast?s most coveted beach town. "SoCe", named for the ideal location South of Central Avenue in Olde Naples, walking distance to the beach and elegant 5th Ave S shopping and dining district.