Holiday rentals in Naples

4.98 out of 5 average rating, 133 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!

4.94 out of 5 average rating, 125 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!

4.96 out of 5 average rating, 122 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).

5 out of 5 average rating, 17 reviews

Cozy and Stylish, 2 King, Close to Beach & 5th Ave

Nestled on a tranquil street in the heart of Naples, this newly renovated retreat offers the perfect mix of modern comfort and coastal charm. Step outside to a chic outdoor living area, perfect for enjoying your morning coffee or relaxing in the evening breeze. Just minutes from renowned 5th Avenue and pristine beaches, it's easy to enjoy the best of the area. Plus, we provide all the beach essentials — chairs, umbrellas, and towels — so you can fully relax and enjoy the sun-soaked paradise.

5 out of 5 average rating, 22 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 not heated. You have use of 1/2 of dock.

5 out of 5 average rating, 30 reviews

Villa in Naples

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!

4.98 out of 5 average rating, 181 reviews

Gulf Access Sanctuary, Kayaks, Bikes, ebikes

A renovated mid century modern house with natural peaceful views out of every window and slider. No detail spared, as it was going to be our forever home. Located on an ocean access canal, extremely safe, quaint and friendly neighborhood, just off 41. The backyard has a large shaded sitting area with a gas grill and fire pit. The dock hangs over the water with seating and swim ladder. 2 tandem kayaks, fishing rods & tackle, adult & children’s bicycles, beach chairs, and so much more.

4.96 out of 5 average rating, 108 reviews

Home in Naples Park

The Beach Getaway Home only steps from the water!

Perfect location for a beach getaway! Centrally located, enjoy all of Naples in the Naples Park neighborhood. Less than half a mile from Vanderbilt beach, walk or bike to the sunny gulf coast in under 10 minutes. Also steps away from the Ritz Carlton tiki bar! Shop groceries at the nearby Whole Foods, Trader Joes, and Publix. Feel like an evening out that's close by? Enjoy the Mercato shopping and dining area with several bars, restaurants, nightclubs, and even a movie theater.

4.9 out of 5 average rating, 111 reviews

Charming Heated Pool Villa - minutes from beach

Self check-in in this charming villa and live like a true local in Naples. We're within driving distance to restaurants, shops, and beaches. Our place comes with 4 bedrooms, 3 baths, and a private pool. Completely fenced, ideal for kids and pets to play safely while enjoying the ultimate coastal comfort. Located in a low traffic, low noise area. Ample parking space, and spacious front and backyard. Ideal for parking large vehicles, RVs, boats, and hosting multiple families.

4.96 out of 5 average rating, 107 reviews

Tropical paradise 5 minutes from the beach

Come on in and unwind in this peaceful and one-of-a-kind oasis just a short 5-minute drive from Wiggins Pass beach! Feeling adventurous? Hop on a bike and you'll be there in a little over 15 minutes. Located in North Naples, this charming house is fully stocked with everything you need to cook, discover, unwind, and rejuvenate, this space even boasts its own private backyard. The moment you pull into the driveway, you'll instantly feel those vacation vibes.

4.95 out of 5 average rating, 131 reviews

Three Palms Oasis - 2 Miles to Beach and 5th Ave

We invite you to stay at this stylish, yet affordable luxury home with a gourmet kitchen right in the heart of central Naples. Three Palms Oasis is located in a quiet coastal neighborhood under two miles from the best that downtown Naples has to offer including the sugar white sand beaches, Naples Design District, dining and shopping on 5th Ave, Naples Zoo, Olde Naples, and so much more! You won’t find a better value in the prestigious 34102.

5 out of 5 average rating, 64 reviews

Home in Naples Park

Luxe King EnSuites ·Heated Saltwater Pool/Spa

Welcome to 716 Coastal Dreams! This stunning coastal vacation home, a luxurious, new build 5-bedroom w/ 3 kings and 1 double queen ensuite that combines the timeless allure of the seaside with modern elegance. Nestled in a serene coastal enclave, this property offers the perfect escape for those seeking relaxation, comfort, and the allure of the ocean. · · · Book NOW before this Beautiful Home becomes a well known Treasure! · · ·

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Naples holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Naples's top sights

Naples Beach110 locals recommend

Waterside Shops116 locals recommend

Artis-Naples62 locals recommend

Other great holiday rentals in Naples

5 out of 5 average rating, 86 reviews

Apartment in Old Naples

Little Gem By the Beach and 5th w/Patio Old Naples

JimRating, 5 stars2 weeks ago

Would thoroughly recommend Bruce and Patti's condo. It was spotlessly clean and looks exactly like the photographs. Location is excellent with a short walk to many great restaurants and the beach and a short drive to other amenities. Bruce and Patti were excellent hosts and communication with them was excellent. If we ever come back to Naples we would most definitely stay there again.

4.99 out of 5 average rating, 77 reviews

Home in Naples Park

2br/2ba spacious House near the Ocean

FabiolaRating, 5 stars1 week ago

Beautiful and comfortable home, definitely we are going to come back.

5 out of 5 average rating, 10 reviews

Waterfront w/Pool & Patio - Close to Everything

JulieRating, 5 stars1 week ago

This place is just what our family was looking for. The home was clean, with comfortable beds and nice linens. The pool area had privacy, which was nice. The neighborhood was quiet and we liked being right next to the pickleball courts. We did a lot of fishing off the back dock catching catfish and snapper. Only a few miles from the beach. Some great local restaurants nearby. Dara was responsive and helpful with any questions I sent her way. Overall, would highly recommend this stay for a family or friends getaway.

4.97 out of 5 average rating, 39 reviews

Heated Pool, Arcade, <10 min Beach ~ 25 min to RSW

KateRating, 5 stars4 days ago

This place was prettier than I remembered from the photos! The pool area is fantastic, and the overall layout of the house was great. It was very comfortable and clean, and my boys absolutely loved all the fun stuff in the garage! It was only a 5 minute drive to the Foxtail Coffee nearby, as well as many other restaurants and grocery stores. I would definitely recommend it to anyone!

5 out of 5 average rating, 5 reviews

Home in Vanderbilt Beach

Coastal 4BR Retreat - Vanderbilt Beach Pool & Dock

Graham LloydRating, 5 stars7 months ago

We holiday twice a year in and around the waterways. This property is without doubt the best we have stayed in. The location, the furniture, everything in the house was excellent. Crissy was always on hand and on a couple of occasions had some items delivered immediately to the house…. Such a superb host and a pleasure to deal with. Nothing was a problem at all for her…. Thank you for a wonderful holiday!

Superhost

4.89 out of 5 average rating, 28 reviews

Charming Waterfront Tropical Escape Near Downtown

SharonRating, 5 stars2 months ago

An Unforgettable Tropical Getaway! This Airbnb is truly a hidden gem! Nestled right on a serene lake, the property offers a perfect blend of luxury and natural beauty. From the moment we arrived, we were blown away by the stunning landscape—lush tropical greenery, swaying palms, and a peaceful water view that made every morning feel like a dream. The home itself is absolutely gorgeous. Every room is stylishly decorated with antique high-end touches that still manage to feel cozy and inviting. You can tell a lot of thought went into every detail—from the plush furnishings to the vibrant artwork and elegant lighting. We spent our days lounging by the crystal-clear pool and our evenings by the fire pit, watching the sun set over the lake. Whether we were sipping coffee on the patio or enjoying a relaxing swim, every moment here felt like pure bliss. This home is everything you need for a luxurious vacation, relaxing escape or peaceful retreat. Thanks Marco!

5 out of 5 average rating, 16 reviews

Home in Old Naples

Beach Access Modern 3BR w/ Pool

JennyRating, 5 stars2 weeks ago

We had a great experience at this Airbnb! The place was exactly as described clean, cozy, and thoughtfully decorated. The location was perfect close to the beach. Our host was incredibly kind and responsive, making check-in and communication smooth and stress free. We appreciated the little touches, like fresh towels and well stocked kitchen. It truly felt like a home away from home. We would definitely stay here again and highly recommend it to anyone looking for a great place to stay!