Holiday rentals in Naples

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Top-rated holiday rentals in Naples

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Top guest favourite

Home in Naples

4.99 out of 5 average rating, 136 reviews

POOL HOUSE, CLOSE TO THE BEACH & DOWN TOWN NAPLES!

HEATED Pool home - Completely renovated home that comfortably sleeps 6 Only 5 minutes to the most desirable Beaches in the USA! Also very close to incredible restaurants, Publix, Target, Shopping, Parks and only 10 minutes to Downtown Naples. Flat-Screen TVs, Hi-Speed Internet, Comfy beds, modern and fully-stocked Kitchen. Very private and large pool with outside grill and patio furniture. Perfect for relaxing after a long day at the beach, we look forward to welcoming you to our HAPPY PLACE!

Guest favourite

Home in Naples

4.94 out of 5 average rating, 127 reviews

LUXE Oasis | 10 min Beach+5th Ave | HTD Pool• 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

Home in East Naples

4.96 out of 5 average rating, 125 reviews

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).

Top guest favourite

Villa in Naples

5 out of 5 average rating, 32 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!

Guest favourite

Home in Naples Park

5 out of 5 average rating, 6 reviews

LUXURY: Custom 4BR Home w/ Pool & Spa

NEW! From Long Time Super-Host. Check my profile to read reviews from other homes. This luxurious custom home offers the ultimate blend of modern comfort and resort-style amenities. With 4 bedrooms and 3.5 bathrooms, our retreat comfortably hosts up to 9 guests, ensuring plenty of space to relax and recharge. Located within 1 mile of Vanderbilt Beach (bike or walk!), dining & shopping, our home is the perfect launching pad for exploring the area’s natural beauty or enjoying a serene escape.

Top guest favourite

Home in Naples

5 out of 5 average rating, 17 reviews

Modern Home in Naples w/ Heated Pool

Experience luxury in this newly renovated home with stunning lake views and southern exposure. The expansive lanai features a brand-new, oversized pool. Inside, enjoy all-new flooring, stainless steel appliances, quartz countertops, chic bathrooms, and a linear fireplace. Located in Berkshire Village, it’s 3 minutes from Berkshire Commons and 20 minutes from downtown Naples. Fully furnished with a two-car garage and lush landscaping, this home offers refined living and a relaxing retreat.

Top guest favourite

Home in East Naples

5 out of 5 average rating, 25 reviews

Blue Banyan Boathouse w/heated POOL. Boat DOCK!

POOL! 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, 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/drinks/BBQ poolside. Pool is heated. You have use of 1/2 of dock.

Top guest favourite

Apartment in Park Shore

5 out of 5 average rating, 19 reviews

Westshore 1201 at Naples Cay

Welcome to our condo with amazing views where you can enjoy the peaceful grounds with amazing views of the ocean, bay and Clam Pass. We are located on the 12th Floor of Westshore of Naples Cay Complex. Forget your worries in this spacious & serene space, watch the beautiful sunsets from our private balcony and listen to the waves as the sun rises. We are just a short walk from our private beach with amazing views. Our complex is a gated community that provides 24-hour security.

Top guest favourite

Home in Naples Park

5 out of 5 average rating, 8 reviews

Luxurious "Villa in the Hills"

Welcome to your perfect vacation getaway! This newly remodeled two-story home offers luxury and comfort for groups of all ages. Spacious indoor living space and exquisite outdoor area is providing everything you need for extended family and friends to get-together. This 3 bedroom and 3.5 bathroom home is located only 4 minutes away from the Vanderbilt Beach, night life in Mercato and various magnificent restaurants. Let us help you to build unforgivable memories!

Top guest favourite

Apartment in East Naples

5 out of 5 average rating, 7 reviews

Naples Tyme Retreat

New spring rates! Enjoy Spring at Naples Tyme Retreat — 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. 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.

Top guest favourite

Home in Old Naples

5 out of 5 average rating, 18 reviews

Beach Access Modern 3BR w/ Pool

Welcome to your ideal getaway in the vibrant heart of Old Naples! This stylish 3-bedroom retreat is just a few blocks from stunning beaches, inviting you to experience the perfect blend of relaxation and coastal adventures. Our home is ideal for families, couples, and friends looking to make the most of their vacation. Whether you're lounging by the pool, taking a sunset walk to the beach, or enjoying a gourmet meal prepared in your modern kitchen.

Guest favourite

Home in Naples Park

4.93 out of 5 average rating, 148 reviews

675 FantaSea | New Heated Resort Pool & Fire Pit

Spend the day outside morning, noon & night and live out your FantaSea vacation! Lounge on the deck or in the heated pool on the sun shelf. On a cool night sit by the fire and relax in the Adirondack chairs. Desirable designer interior with coastal decor has the comfort of home with the feel of the sea. We are just a few minutes away from white sandy beaches with beautiful sunsets, amazing restaurants and upscale shopping centers.