Holiday rentals in Keewaydin Island

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Top-rated holiday rentals in Keewaydin Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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 Naples
4.95 out of 5 average rating, 109 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

Guest favourite
A serene beach scene captures a vibrant sunset, with hues of pink and orange reflected on the water's surface. Gentle waves lap at the shoreline, while soft sand stretches along the beach, interspersed with small scattered shells.
Home in Naples
4.96 out of 5 average rating, 99 reviews

Magical Gateway in Naples FL

You'll fall in love with this tinny but magical place in the heart of Naples, modern open concept,high end finishes, a lot light, 2 BR queens beds, fine blinens, full bathroom with marble, enclosed pool, spacious back yard and a wood burning fire pit, 2 parking spaces just few steps from your front door. This place is near to all Naples has to offer, beautiful beaches, dining & nightlife, it is only 3km from the beach, 3 km from 5th ave in Old Naples and less than a mile from shopping centers.

Top guest favourite
A spacious covered porch offers a view of a tranquil lagoon surrounded by tropical foliage. Comfortable outdoor seating is complemented by a small table, while vibrant flowers are arranged in a vase. Sunlight reflects off the water, enhancing the outdoor ambiance.
Home in Naples
4.96 out of 5 average rating, 160 reviews

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!

Top guest favourite
A spacious screened-in lanai features a heated pool with a shallow area for children. Luxury chaise lounges are positioned near the pool, offering comfortable seating. The outdoor space is designed for relaxation and enjoyment, with clear views of the surrounding greenery.
Home in Naples
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!

Top guest favourite
A bright living area features large glass sliding doors that open to a private patio with views of lush greenery. A round dining table with four chairs is positioned adjacent to the doors, while a dark sofa is placed nearby, creating a welcoming and open atmosphere.
Cottage in Naples
4.98 out of 5 average rating, 182 reviews

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!

Top guest favourite
A spacious heated pool invites relaxation, surrounded by lounge chairs placed along the deck. Lush palm fronds frame the view, enhancing the tropical ambiance. The pool area is well-maintained, with clear water reflecting the sun. Parking is visible beyond the poolside greenery.
Apartment in Naples
4.93 out of 5 average rating, 128 reviews

NEW! ONE BLOCK to the Beach, Restaurants & Shops!

Welcome to your newly renovated condo in the heart of Olde Naples! Just ONE BLOCK to the beautiful Naples beaches and all of the shops and dining on 3rd Street! Your first floor condo suite is ideally situated just steps from the oversized heated pool. And with large windows you can let that warm Florida sunshine in. The studio also has a designated parking space, common laundry, kitchen, bathroom, dining table, king size bed, pull out single trundle bed and can sleep up to 3 people.

Top guest favourite
A vibrant blue island home with a welcoming front entrance, surrounded by manicured green grass. Lush tropical plants and flowering shrubs enhance the landscape. A paved driveway leads to a single-car garage, under a light-colored roof, set against a bright sky.
Home in Naples
4.97 out of 5 average rating, 255 reviews

Island lifestyle family vacation home (Salt Pool)

A stylish, brand new island home perfect for vacationing with your own private heated pool. The West Hilo Home sleeps 8 and is within 3 blocks of local restaurants that feature dining on the water in sunny Isles of Capri. Enjoy laid back island life- including kayaking, boating, fishing and jet skiing just minutes away. Neighboring Marco Island is less than 10 minutes by car and famous for their powder white sand beaches. Or relax at home grilling by the pool while the sun sets.

Top guest favourite
Home in Marco Island
5 out of 5 average rating, 29 reviews

New Luxury 4 Bed Home with Heated Pool

New Construction Luxury 4 Bed Home with Heated Pool , Outdoor Kitchen/Bar and Lagoon Water View! NO BOOKING GUESTS UNDER 30 yrs OLD. NO PETS. NO SMOKING inside or outside. SEE DETAILS TO NOTE (LEGAL AGREEMENT) Owner/Mngr 10 min away for emergency New Home Only 10 minutes from Marco Island Beaches and 5 minutes from restaurants. Two master beds with bathroom Loft extra sleeping area has Queen pullout sofa, walk in closet and balcony. beach cruisers parked in the garage.

Top guest favourite
An outdoor dining area is highlighted by a large wooden table surrounded by woven chairs. Pendant lights hang above, casting soft illumination. A swimming pool with clear water is visible through a screened enclosure, complemented by lush greenery in the background.
Home in Naples
5 out of 5 average rating, 35 reviews

Mediterranean Inspired Villa with Private MiniGolf

Welcome to our Mediterranean-inspired villa, where luxury meets comfort in the heart of Naples. Nestled just 15 minutes from the beach and downtown, our home features one of the largest private putting greens and pools in the area. With 4 inviting bedrooms and 3 spacious bathrooms, our villa comfortably hosts 8 adults or a mix of 6 adults and 6 children. It’s the perfect vacation home for the whole family. Enjoy the blend of relaxation and adventure in our tropical paradise.

Guest favourite
The illuminated pool glistens in a tranquil setting, adorned with floating yellow lily candles. Lounge chairs with striped towels are positioned beside the water, while soft lights provide ambiance around the area, creating a serene space for relaxation.
Home in Marco Island
4.97 out of 5 average rating, 143 reviews

Top-rated luxury pool home in prime location

💰No nickel & diming — AirBnb & cleaning fees in nightly rate! 🏠Newly renovated & professionally designed 👙Amazing pool and outdoor kitchen (including grill, pizza oven, fridge)! 🏖️4 mins to beach 🌊Beach chairs, umbrellas, beach wagon & bikes 🐶Low pet fee; we love our 4-legged guests! ✅Fully stocked chef’s kitchen 🛌🏽Super comfortable beds for ultimate comfort and sleep 💻 High speed internet with dedicated workspace 😊24/7 local & professional host support!

Top guest favourite
A bright studio features a queen-sized bed with a turquoise coverlet and decorative pillows. Natural light floods the room, highlighting the light wood flooring and modern furnishings. A small dining area is visible, with artwork showcasing a coastal theme.
Flat in Naples
5 out of 5 average rating, 30 reviews

Naples Gem | 10Min Beach | BBQ | Patio | Parking

We want to be your Host in Naples! Let us show you why you should book with us: Top Location: - 10 min to Beaches - 8 min to Downtown - 5 min- Rentals- paddle board, kayak & boat - 5 min- Sightseeing, sunset & fishing cruises - 30 Min to Marco Island - Smart TV - Fast WIFI - Fully equipped kitchen - Dedicated work space - FREE Onsite parking - Quiet and Safe Area - Private Patio - BBQ - Outside dining - Beach supplies - Self check in & Hosts available 24/7

Guest favourite
The exterior of Turtle Bungalow is framed by tall palm trees and lush greenery. A shaded seating area is arranged under a large umbrella, accompanied by a table and chairs. Decorative elements, such as a small statue and potted plants, enhance the entrance.
Guest house in Naples
4.91 out of 5 average rating, 126 reviews

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.

Popular amenities for Keewaydin Island holiday rentals