Waterfront holiday rentals in 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.

505 Sunset Key Estate | Luxury Courtyard Pool Home

Welcome to 505 Sunset Key Estate | Luxury Courtyard Pool Home Located on the coveted Vanderbilt Drive, this 5BD, two-story, heated pool home features Old Naples Charm w/ a North Naples location. Enjoy breathtaking sunsets from the private balcony or take a short stroll to world class, white sand beaches. Professionally designed to give you a sophisticated vacation home away from home. The upmost attention was paid to selecting quality furnishings that are as functional as they are beautiful!

Park Shore Resort Modern Top Floor 2 Bed 2 Bath

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!

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

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.

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!

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.

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.

2 Kings, Pool, Gulf Canal, Game Room and Kayaks

Unwind Cape Coral welcomes you to sunny southwest Florida, close to magnificent beaches, fishing, shelling, Minnesota Twins Spring Training & much more. Come enjoy this new construction home with heated pool, Kayaks, heated and cooled game room (PlayStation 5), gulf access - salt water canal, 4k oled tv's & many more refreshing amenities. You will love this clean & bright home with lovely décor. Located in the highly sought after Pelican neighborhood of Southwest Cape Coral!

Park Shore Resort-BLDGC#218*Amazingly remodeled*

*REMODELED 2024* One of the Nicest & most luxurious condos at PSR-Top Floor condo. This condo has been lovingly restored. Park Shore Resort has all the amenities you could want with an on-site restaurant, Heated Pool, BBQ's, Tennis, Pickleball courts, Basketball, Exercise room. In the middle of Naples walking distance to numerous Restaurants & Shops within minutes to the Village Shops on Venetian Bay, Mercato, Waterside Shops, and of course Naples Famous Beaches.

Waterfront w/Pool & Patio - Close to Everything

Discover your perfect Naples getaway at our charming canal-front home. Featuring 3 bedrooms & 2 bathrooms, this retreat offers a private dock for kayaking and fishing adventures right from your backyard. Relax by the refreshing pool, or enjoy alfresco dining on the spacious patio. You'll have easy access to pristine beaches, delicious dining, and all the best Naples has to offer. Experience the tranquility and beauty of waterfront living in this idyllic setting.

Waterfront "Casa del Lago" Private Pool & Jacuzzi

Welcome to your dream vacation home in sunny Florida! This luxurious retreat offers a spacious 4BR/3BA Cape Coral waterfront villa for 8 with a private pool, hot tub, chef’s kitchen, free parking, pet-friendly policy, and reliable Wi‑Fi—perfect for families, couples, business travelers, and remote workers. Casa del Lago is a luxurious waterfront getaway designed for those who seek both relaxation and indulgence.