Holiday houses 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 modern pool area is featured with a spacious swimming pool surrounded by a screened-in lanai. Lounge seating and vibrant cabanas are positioned nearby, providing shaded relaxation. An adjacent game room is visible, equipped with a pool table and foosball table under unique lighting.

Home in Naples

4.96 out of 5 average rating, 116 reviews

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.

Top Guest favourite

The kitchen features modern appliances with a clean design, including a stove, microwave, and refrigerator. A wooden island with two white chairs is positioned in the center, complemented by red pendant lights. Natural light enters through a window adorned with light curtains, enhancing the inviting atmosphere.

Guest suite in Naples

4.98 out of 5 average rating, 429 reviews

Naples Loft-private-18 min to the beach

Beautiful newer construction loft that offers 640 square feet of open floor plan! This unit sits above our two car garage , 130 feet from the main house. Full kitchen, microwave, coffeemaker, toaster, iron, and washer/dryer! Our home sits on 1.14 acres with a circular driveway in a very quiet neighborhood. Enjoy organic farm fresh eggs when the hens are laying. If you have children, your welcome to play in the "island" (our kids play area) with a playhouse and climbing dome. Very relaxing place!

Guest favourite

An inviting collage showcases various areas of the Naples Holiday House. Bright outdoor seating is paired with an umbrella, while the living space features comfortable seating and coastal decor. A cozy dining area invites meals al fresco, and serene beach views complete the relaxing atmosphere.

Home in Naples

4.95 out of 5 average rating, 198 reviews

Home Close To Beach & Downtown Naples

We have stellar reviews, come check us out & see for yourself. Stay at this downtown Naples relaxing 1,864 sqft, 4 BD (2-king beds & 2-queen beds+twin blow up), 2 BA home for the best of vacations. Minutes from 5th Ave beaches/shopping/food/activities. Bonus: 2 outdoor seating areas/ample entertaining space/BBQ/outdoor games (corn hole, jenga, putting green), 2 bikes & beach equipment for 8. If looking for a pool, we have resort access to 6 area resort pools (day rate fees apply). Message me!

Guest favourite

Home in Naples

4.93 out of 5 average rating, 14 reviews

Villa Nautilus by Downtown

This beautifully renovated townhouse blends modern comfort with laid-back Florida vibes. Located just minutes from Naples’ stunning beaches, top-rated restaurants, boutique shops, and local hotspots—you’re in the heart of everything. Spend your days sunbathing or paddle boarding. In the evening, take a quick bike ride down to Celebration Park, where food trucks, live music, and waterfront drinks await. Visiting for the US Open Pickleball Championships or Cars on 5th? We're ready to host you!

Top Guest favourite

Condo in Marco Island

5 out of 5 average rating, 19 reviews

Luxury Coastal Condo - Pools, Tennis & Bay Views

Surrounded by swaying palm trees & tropical breezes, enjoy assigned undercover parking, screened lanai overlooking pool & bay, luxury comforts for five (king bed, queen pullout, twin pullout), equipped kitchen & bath, mini bar, coffee bar with tea & coffee, vanity/work station, two 65” TVs, beach chairs, umbrellas, towels, totes, cooler, wagon, sand toys, Bluetooth speaker, WiFi, pools and hot tubs, tennis, on-site restaurant. Walkable to restaurants, bars, fitness studios, shops, Rose Marina.

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, 100 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 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, 133 reviews

LUXE Oasis | 10 min Beach • HTD Pool+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 spacious screened lanai features a private pool surrounded by lounge chairs. A BBQ grill is positioned nearby, and a glimpse of the indoor living area is visible through large glass doors. Lush greenery offers a natural backdrop to this relaxing outdoor space.

Villa in Naples

5 out of 5 average rating, 37 reviews

Salt Pool Oasis: 5 Miles to Beaches (4BD/3BA)

Tranquil Naples Oasis: 5 Miles to Beaches! Updated, family-friendly 4BD/3BA home, just 5 miles from Lowdermilk, 5th Ave, and Clam Pass beaches. Quiet, safe, gated cul-de-sac community with sports amenities. Relax in our screened lanai: salt pool, grill, loungers, egg chairs, indoor/outdoor flow. Perfect for family gatherings and relaxing afternoons. Enjoy white linens, a fully stocked kitchen, and easy access to all Naples has to offer, 15 minutes away! Your perfect family getaway awaits!

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

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.

Top Guest favourite

A well-lit bedroom features a spacious bed adorned with decorative pillows and a soft blanket. Two windows with light-filtering shades provide natural light. A minor desk is placed beside a comfortable chair, complemented by stylish blue accent pieces against neutral walls.

Apartment in Naples

4.94 out of 5 average rating, 68 reviews

Coastal Retreat - Bayshore Arts District

Welcome to your Cozy Bayshore Retreat! Step into this beautifully decorated, brand-new apartment designed for comfort and relaxation. Located just minutes from the stunning Bayshore district and close to the beautiful Naples beach, this charming space offers the perfect blend of convenience and serenity. Whether you're here for a weekend getaway or an extended stay, you'll love the thoughtful touches, stylish decor, and unbeatable location. We are pet-friendly! :)

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.

Apartment in Naples

5 out of 5 average rating, 32 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