Naples Vacation Rentals Apartments, homes, condos, and townhomes to elevate your stay in Florida’s Paradise Coast. Where Florida Greater Naples Area 34103 Beach Naples Beach Area 34108 Naples Park and Mercato 34112 Southern Naples Naples Park and Mercato Other Naples Neighborhoods 34110 Strand 34119 and 34120 Golf Amenities-Resort neighborhoods - People 1 + 2 + 3 + 4 + 5 + 6 + 7 + 8 + 9 + 10 + 11 + 12 + 13 + 14 + 15 + 16 + 17 + 18 + 19 + 20 + 21 + 22 + 23 + 24 + 25 + 26 + 27 + 28 + 29 + 30 + 31 + 32 + 33 + 34 + 35 + 36 + 37 + 38 + 39 + 40 + Search View all Naples Properties USA > Florida > Naples Visit Naples Ecotourists, art lovers, foodies, and water adventurers flock to Naples–the gem of Florida’s Paradise Coast. Sun-drenched weather, culture, and upscale offerings make this South Florida jewel the ideal getaway. Navigate the mangrove tunnels and paddle alongside resident manatee or venture out to kayak on the open water. Pack the sunscreen, a bestseller, and a chair to stake out the perfect dolphin-watching spot along the miles of sand. Anglers, Naples offers every kind of fishing where you can cast a line from a pier in the morning then head out and deep-sea fish or try your luck at one of the area’s lakes. Golfers can perfect their game at one of the area’s 90 courses–a true golfer’s paradise. Add in shopping, top-notch dining, and entertainment, Naples ticks all of the beach vacation boxes. Your Naples Vacation, Your Way.Long Term StaysGood for GroupsOn the Golf Course Find Your Naples Rental New PropertyFeatured PropertyFlexible Cancellation Naples Park Pet-Friendly Pickleball 4BR w/ Pool, 800 Block Steps from Beach Naples, FL 4 Bdrms 2 Baths 8 Guests Pet Friendly From $175.00 per night + taxes & fees View Details New PropertyFeatured Property Twin Eagles Golf Pickleball Bald Eagle Way Naples, FL 4 Bdrms 4 Baths 8 Guests Pet Friendly From $435.00 per night + taxes & fees View Details Featured Property StoneCreek Tesla Charger Remote Work Naples, FL 5 Bdrms 4 Baths 10 Guests From $440.00 per night + taxes & fees View Details New PropertyFeatured Property Unit 1 Bungalow Pickleball Championships Naples Park 102nd Option to combine bungalows Naples, FL 2 Bdrms 2 Baths 4 Guests Pet Friendly From $150.00 per night + taxes & fees View Details New PropertyFeatured Property Unit 2 Bungalow Pickleball Championships Naples Park 102nd Private Pool Naples, Florida 3 Bdrms 2 Baths 6 Guests Pet Friendly From $225.00 per night + taxes & fees View Details Covent Gardens Twin Eagles Full Golf Privileges Naples, FL 3 Bdrms 2 Baths 5 Guests From $204.00 per night + taxes & fees View Details New PropertyFeatured Property Harborside Terrace Belair Lane_original Naples Naples, Florida 2 Bdrms 2 Baths 4 Guests From $164.00 per night + taxes & fees View Details New PropertyFeatured Property Sunset Haven Christmas Pickleball Championships April 26 Naples, FL 3 Bdrms 3 Baths 6 Guests From $574.00 5.0 per night + taxes & fees View Details New PropertyFeatured Property Kinross Twin Eagles Full Golf Transfer Kinross Naples, FL 2 Bdrms 2 Baths 6 Guests From $420.00 per night + taxes & fees View Details New PropertyFeatured Property Vacation and Pickleball Championships at Strand First Floor Condo Naples, FL 2 Bdrms 2 Baths 4 Guests From $171.00 per night + taxes & fees View Details New PropertyFeatured Property Full Bungalow Pickleball Championships Stay here Naples Park 102nd Private Pool Naples, Florida 5 Bdrms 4 Baths 10 Guests Pet Friendly From $495.00 per night + taxes & fees View Details Search while moving Featured Naples Vacation Rentals From $150 / night Unit 1 Bungalow Pickleball Championships Naples Park 102nd Option to combine bungalows Naples, FL 4 Guests 2 Bdrms 2 Baths From $574 / night Sunset Haven Christmas Pickleball Championships April 26 Naples, FL 6 Guests 3 Bdrms 3 Baths From $420 / night Kinross Twin Eagles Full Golf Transfer Kinross Naples, FL 6 Guests 2 Bdrms 2 Baths From $171 / night Vacation and Pickleball Championships at Strand First Floor Condo Naples, FL 4 Guests 2 Bdrms 2 Baths From $225 / night Unit 2 Bungalow Pickleball Championships Naples Park 102nd Private Pool Naples, Florida 6 Guests 3 Bdrms 2 Baths From $175 / night Naples Park Pet-Friendly Pickleball 4BR w/ Pool, 800 Block Steps from Beach Naples, FL 8 Guests 4 Bdrms 2 Baths From $440 / night StoneCreek Tesla Charger Remote Work Naples, FL 10 Guests 5 Bdrms 4 Baths From $435 / night Twin Eagles Golf Pickleball Bald Eagle Way Naples, FL 8 Guests 4 Bdrms 4 Baths From $495 / night Full Bungalow Pickleball Championships Stay here Naples Park 102nd Private Pool Naples, Florida 10 Guests 5 Bdrms 4 Baths From $164 / night Harborside Terrace Belair Lane_original Naples Naples, Florida 4 Guests 2 Bdrms 2 Baths Your Local TeamLocally Owned and Operated In NaplesRemember, when you rent with SkyRun, you can expect superior, prompt, and personalized service that’s hard to find in a top-down rental corporation. Enjoy a personal relationship with your property manager, who can answer any questions and address all concerns promptly. Have a question about local activities, amenities, or services? Our local staff can provide recommendations for getting the most out of your stay. Our property managers are just a stone’s throw away from most of our rentals. That means they’re available to step in to help with any situation. With a robust background in operations, sales/marketing, and customer service, Kimberly embodies a wealth of expertise perfectly suited for enhancing your travel experience. Drawing from her successful journey of managing her own vacation home and an intimate knowledge of Naples’ local areas, she is excited to share her insights with travelers. Kimberly is dedicated to ensuring your stay is seamless and memorable, offering personalized recommendations and exceptional guest services to make your vacation truly extraordinary. Kimberly LaytonNaples, FLOwnerLet's Talk! Beaches Notable Areas Things to Do Dining Property Damage Waiver Travel Insurance Check-In Instructions Naples BeachMore than 10 miles of Gulf coastline entices beachcombers to find their favorite spot in the sand. Swimmers love to jump the waves, splash around, or get in some fitness in these calmer waters. Naples Pier is still a popular spot, despite suffering some recent damage. This spot is close to Downtown Naples and serves up points of access for kayakers and paddleboarders. Vanderbilt BeachVanderbilt Beach’s popularity during peak season makes it a key spot for sun lovers and swimmers alike, so try to arrive before 10 am to snag a parking spot. Once you feel the soft, white sand under your feet and gaze at the turquoise waters, you’ll see why this North Naples spot earns its reputation as one of the town’s most stunning beaches. Barefoot Beach The perfect stretch of Naples coastline for people who want to escape the crowds and bathe in Florida sand and sun. Explore the more than two miles of azure coastline that sea turtles call home. Scour the shoreline to add to your shell collection or grab your kayak to explore the estuaries that weave through the park. Pack a picnic–no concession stands in this natural wonderland. Vist website Island of Keewaydin Keywaydin Island is an 8-mile long barrier island located between Naples and Marco Island, Florida and is part of the pristine Rookery Bay Reserve. Keewaydin is largely undeveloped and offers miles of soft white sandy beaches and is only accessible by boat. Visit website Nearby Marco Island With pristine beaches, swaying palm trees, and the unmistakable Gulf breeze, Marco Island ticks all the paradise getaway boxes. Beaches, nature, and adventure beckon guests. Unwind at Tigertail Beach and fill your bucket with shells or explore the nearby Everglades–watch for crocs! And the sunsets here? Pure magic. Culture abounds, too, from the Marco Island Center for the Arts to the eclectic shops at Marco Walk Plaza–feel the creative energy infusing island life. If you’re up for the ideal mix of coastal beauty, relaxation, and a touch of Floridian adventure, Marco Island needs to be on your list. Fifth Avenue SouthUpscale shopping and dining meet Florida outdoor living. This walkable retail haven acts as Naples’ unofficial Main Street and when you amble through the boutiques and shops that serve up an Old Florida vibe, you’ll see why Fifth Avenue South draws in locals and visitors alike. Relax with a cocktail or coffee at the area’s bars and cafes, or indulge in some of the area’s best cuisine. Want to check Fifth Avenue South out before you’re in town? The area even has its own podcast for you to learn about this Naples hub. Third Street South The 19th century Naples Pier, Gulf winds dancing across your face, a leisurely cocktail sipped al fresco? Third Street South’s offerings have delighted visitors and locals since the 19030s. The Florida sun gives life to lush landscaping that elevates the area and seasonal events like the summer Farmer’s Market and Semi-Annual Sidewalk sales might just make your stay more memorable. Lowdermilk ParkSand volleyball, a playground, picnic tables, gazebos for rent, and ADA beach access mats invite everyone to visit Lowdermilk Park for the perfect beach day. Open from 5 am to 11 pm. Private Chef, Chef Anthony SantosIndulge in a culinary journey with Chef Anthony Santos, who brings exquisite flavors and personalized service right to your table. With years of experience and a passion for crafting memorable dining experiences, Chef Anthony transforms any meal into an extraordinary event, perfect for intimate gatherings or special celebrations. Learn more here. Anchor Private Yacht RentalsSet sail in luxury with a private yacht rental, offering options both with and without a captain to suit your preferences. Whether you prefer a guided tour or the freedom to explore at your own pace, these yachts promise an unforgettable experience on the open water. Learn more here. Bark of the ArkPure Florida’s popular Bark on the Ark, a dog friendly cruise is a monthly event for the whole family. The fun cruise takes guests and their pups aboard the M/V Edison Explorer for a sightseeing eco cruise along Naples Bay to Keewaydin Island. Cruises depart from Tin City, located at 1200 Fifth Ave. S., Naples. Visit website Rising Tide ExplorersRising Tide Explorers gives you the opportunity to experience some of Naples & Marco Island’s most beautiful natural areas with kayak rentals and exciting adventures led by the region’s only team of 100% active local biologist guides. Visit website Naples ZooWhether you’re exploring with family, friends, or on a solo adventure, the Naples Zoo promises an enriching and heartwarming experience. Come join us for a day of discovery, where every step brings you closer to the fascinating world of wildlife. Visit website Naples Pier For the perfect blend of relaxation and excitement, the Naples Pier is the place to be. Whether you’re capturing a stunning sunset, savoring the coastal breeze, or simply immersing yourself in the vibrant atmosphere. Visit website Naples Princess Naples Princess Cruises offer opportunities to soak in the sunshine or enjoy the climate controlled air-conditioned salons as you cruise past the multi-million-dollar homes of Port Royal and see the sunset drop from the Gulf of Mexico in Naples Florida. Visit website Extreme Boat Rentals in NaplesDiscover hidden coves, race across the waves, and explore the Gulf of Mexico like never before. Visit website Everglades from Naples Embark on a wild expedition from Naples to the untamed beauty of the Everglades! Immerse yourself in the heart of Florida’s unique ecosystem, just a short drive from the charming streets of Naples. Visit website Miss Naples Catamaran Cruise Set sail for an unforgettable experience with Miss Naples Catamaran Cruise! Departing from the picturesque shores of Naples, this catamaran journey promises a perfect blend of luxury, relaxation, and the mesmerizing beauty of the Gulf of Mexico. Visit website Cruisin Tiki’s Floating fiesta that blends the charm of a tiki bar with the beauty of Naples’ coastal scenery. Visit website Naples Depot and Train Museum The mission of the Collier County Museum Division is to engage residents and visitors in appreciation and understanding of our communities’ unique heritage and cultural development. Visit website Koresha State Park Koresha State Park is a picturesque natural reserve known for its diverse wildlife, scenic hiking trails, and serene lakes, making it a popular destination for nature enthusiasts and outdoor activities. Visitors can enjoy camping, fishing, and exploring the park’s rich flora and fauna, providing a tranquil escape from urban life. Visit website Naples Botanical GardensParadise blooms at this tropical flora wonderland. Let the colors from hints of pink to full-on fuchsia dazzle and the tropical fruits tempt all of your senses. Go to extremes with aquatic plants to cacti and succulents and check out the rotating exhibitions and events that entertain and educate. Visit website Sugden Community Theater Sugden Community Theater in Naples is a vibrant cultural hub renowned for its high-quality theatrical productions and community events. With its state-of-the-art facilities, the theater offers a diverse range of performances, from classic plays to contemporary shows, enriching the local arts scene. Visit website Artis-NaplesArtis-Naples in Naples, Florida, is a premier cultural institution offering a wide array of artistic performances, including music, theater, and visual arts. Home to the Naples Philharmonic and The Baker Museum, it serves as a vibrant center for creative expression and cultural enrichment in the community. Visit website Get OutdoorsBirders, grab your binoculars, because Naples is an access point to the Great Florida Birding Trail where you can spy limpkins, warblers, and even big guys like storks. Kayakers, book a guided tour and hit the waters of Rookery Bay where your guide will loop you through mangrove water paths and teach you about the ecosystem. For the more intrepid outdoor enthusiasts, guided swamp walks are a one-of-a-kind way to explore the only subtropical wilderness in the US. Spas and WellnessGrab a mat and bliss out with yoga on the beach or elevate your zen with a session of paddleboard yoga. Soothe those sore muscles with a spa treatment at one of Naples’ retreats. Choose from a menu of body work indulgences at one of the larger spas or plan a visit to one of the smaller, local wellness retreats. Namba Premium Grill Selections include mouthwatering Prime Rib Eye, Alaskan King Crab and Whole Tiger Prawn. Known for their meticulous balance of flavors, and exquisitely plated dishes, NAMBA continues to showcase Japanese cuisine to Naples, with innovative flair. Visit website Authentic Tacos at Taqueria San Julian 2 A hole in the wall with fantastic Tacos and Margaritas. Definitely off the beaten path. Fresh salsas made in-house and perfect tacos from chicken, pork, and beef but my favorite is the tongue tacos! Visit website Get to Know Pho at Noodle Saigon Noodle Saigon is a family-owned Vietnamese restaurant serving Vietnamese cuisine with flair in Naples, Florida. For authentic Vietnamese cuisine, visit our Vietnamese restaurant in Naples, Florida. Visit website Table Grilling at Zen Asian BBQ Zen features creative and fresh sushi, Thai dishes inspired by Thai Street food, authentic Korean dishes, and their famous Ramen. Their Korean BBQ features premium meats, fish, lobster and vegetables to be cooked by the guest tableside and served with housemade sauces and several side dishes. Visit website Get Your Sandwich on at Pastrami Dan’sNo table service. No drive thru. No wine. No tablecloths. No silverware. No hostess. No valet parking. No credit cards. No pretense. And you get pastrami, roast beef (with gravy) or a taco with chips. What they do here is just as simple but delicious and done well. Eat like a true local! Visit website Brooks Gourmet Burgers and Dogs Since 2010, Brooks gourmet Burgers & Dogs has been committed to serving the perfect burger. Their all-natural, brilliantly cooked , deliciously crafted burgers are nationally recognized and locally famous. Visit website Homemade Ice Cream at Belgian Yummies Satisfy your hunger for delicately made confections. At Belgian Yummies in Naples, FL, they have an expansive menu of ice creams, cakes, pies, Authentic Belgian waffles, ice cream pops, and ice cream sandwiches dipped in the finest Belgian chocolate. Visit website Riptide Brewery Sip on meticulously crafted beers that tell the story of Naples’ flavor palette. From hoppy IPAs to smooth stouts, Riptide’s diverse selection caters to every taste bud. Visit website Bone Hook Brewing Company Step into a world of flavor and camaraderie as you indulge in the artistry of their handcrafted brews. Visit website Ankrolab Gather your friends, embrace the spirit of discovery, and head to Ankrolab for a taste of Naples’ brewing innovation. Whether you’re a seasoned beer enthusiast or a curious first-timer, their knowledgeable staff is here to guide you through an immersive experience. Visit website Property Damage Waiver Enjoy peace-of-mind with our incidental damage protection. SkyRun includes a property damage protection waiver on each reservation. The damage waiver covers damage to the property up to $1,500 so long as the damage is accidental and reported to SkyRun prior to your departure. It does not cover damage that is willful, the result of negligence, or damaged caused by the misuse of household items. It also doesn’t cover unreported damage. SkyRun doesn’t charge our guests a refundable damage deposit in lieu of the waiver. Unlike a refundable damage deposit, the damage protection waiver is non-refundable. If during your rental of our property, you damage the real or personal property assigned to that property, SkyRun will cover the cost of repairs or the cost to replace the property up to an amount not to exceed $1,500. Should the cost of the damage exceed $1,500 or does not meet the criteria for a “covered loss”, and the property owner’s insurance policy also does not cover the loss, then you shall be responsible for the full amount of the damage which will be charged to the credit card on file. Coverage is provided to you and all travelling companions that are staying in the home overnight during your stay. Coverage is not provided for loss due to: Your intentional acts or gross negligence. Any damage that occurs if you are in violation of the terms and conditions (including but not limited to having more than maximum occupancy or having a party). Loss, theft or damage to any personal effects owned by you or brought on the covered stay by you. Loss, theft or damage caused by any person other than you or your traveling companions with whom you share the property reservation unless substantiated by a police report. Your Duties in the Event of Damage. You must: Take all reasonable, necessary steps to protect the property and prevent further damage to it. Report the loss in writing (email ok) prior to check-out to the SkyRun staff. Provide us documentation such as pictures to substantiate the claim. Travel Insurance Nationwide® Travel Insurance protects your vacation investment against unforeseen events like a hurricane, sickness, injury, flight cancellation, job loss and much more. Group coverage protects everyone in your traveling party for one low price. Get a quote. Check-In Instructions For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if any questions arise. Property Management You Can Trust Owning a vacation rental shouldn’t be stressful. Let SkyRun ease your worries and increase your revenue with our vacation rental management solutions. Why choose SkyRun? As a locally owned & operated business, our homeowners are not just a number to us, they’re our neighbors. But as a franchise, we have access to tools and tech that help you stay ahead of the game. That’s why thousands of second homeowners trust us with their properties. Learn More “My property’s income has doubled in the last year! SkyRun is a great business partner to me and their willingness to listen and grow revenue has been stellar.” Kay JohnsonDestin, FL SkyRun has done an amazing job with my beach condo. They pay attention to every detail and provide incredible service. They are super responsive and go way above and beyond. In just a very short time they have secured a large number of bookings for my unit. Exceptional company to work with and I highly recommend them. Nan S.Sarasota, FL The entire process has been incredibly smooth, providing us with a true sense of peace of mind. From property management to timely payments, it’s been hassle-free. We couldn’t be happier with the service provided by SkyRun. Melissa TaylorW. Bradenton, FL Naples Blog Do I Need Short-Term Rental Insurance for My Vacation Property? Read More How to Turn Your House into an Airbnb: A Complete Guide from Vacation Rental Experts Read More SkyRun Selects PriceLabs’ Revenue Management Platform to Maximize Vacation Rental Revenue Read More SkyRun Named Among Top New & Emerging and Fastest Growing Franchises Read More View All Explore Nearby Areas Marco IslandMiamiFort LauderdaleAnna MariaBradentonSarasotaSiesta KeyLongboat KeySouth Naples Naples Frequently Asked Questions How do I know I’m getting a good vacation rental? SkyRun provides photos, maps, amenity details and reviews about the property you will be renting. Our staff has first-hand knowledge of each property, so don't hesitate to call us if you have any questions. What’s included with my rental? Our rentals come fully furnished including TVs, high-speed internet, linens and towels, a microwave, dishes, pots, pans, and other kitchen essentials. We sweat the details and provide starter supplies like shampoo, conditioner, tissues, paper towels, dishwasher detergent, soaps, trash bags, etc. We provide everything you expect from a fine hotel, and then some. Refer to individual listings to see more amenity information, and please contact us directly if you still have questions. Am I getting a good deal? When you book direct with SkyRun you avoid paying service fees that traditional listing channels charge, like Airbnb. Our prices are also competitive with rent-from-owner rates, but we offer professional service, optional travel insurance, and immediate on-site assistance should the need arise. In addition, we offer exclusive discounts from local businesses, available only to SkyRun guests. SkyRun can help you plan and save on your entire vacation experience, not only the rental itself. How does travel insurance work? Travel insurance is an optional addition to your total rental charges. It is offered on our reservation form at the time of booking. It is also usually offered at the time of booking when you book with a 3rd party booking site. You may also add travel insurance to your reservation within 48 hours of booking. The cost of travel insurance varies and is usually between 7%-9.5% of your total reservation cost, depending on the coverage type. If you do not have travel insurance, you cannot cancel your reservation for any reason. If you have travel insurance and need to cancel or make a claim, refer to your specific policy. How do I rent a property? What are the deposit and payment terms? You can rent any of our properties by booking directly on this website using a credit card or you can call to book a reservation if you would like to speak with a vacation planner. When you book, 1/3 of your total reservation cost, or a minimum of $300, is charged as a non-refundable deposit to secure your rental. Thirty days before your arrival, the remaining amount is due. At this time, the credit card we have on file will be automatically charged for the balance. You may cancel for a full, no-questions-asked refund up to 14 days before your arrival. After that, your payment becomes non-refundable. (See travel insurance above for exceptions). How do I check-in? For most properties, SkyRun utilizes a convenient keypad lock system which allows you to enter your vacation rental using a personalized access code, as opposed to having to pick up a key and worrying about keeping track of it during your stay and returning it afterwards. This also saves you the trouble of coming to a check-in center beforehand. Your welcome packet will be in your rental upon arrival, and our staff is always only a phone call away if questions arise. What are the house rules? You must be 25 years old to rent. No smoking and no pets (unless specifically designated as pet-friendly) are allowed in the rentals. No parties where more than the number of people the property sleeps are allowed in the rental at any time. As in your own home, renters are of course subject to citations for noise violations, etc, handed down by public officials. Remember you are staying as a guest in someone's home, where much investment has been made to make your stay enjoyable; please treat all private property with the respect it deserves. Sign up for emails Trip inspiration, special offers, and vacation planning tips. Name(Required) First Last Email By submitting this form, I agree to SkyRun’s Privacy Policy Δ
