South Naples Vacation Rentals

Paradise is waiting for you in one of South Naples’ rental condos and homes.

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Visit South Naples

South Naples offers sun, fun, and luxury. Relax on pristine beaches, explore coastal waters, or indulge in world-class shopping and dining. Discover nature at local sanctuaries, golf at one of the 90 courses in the greater Naples area, or unwind with a spa treatment that elevates your self-care routine. Take the ferry to carless Keewaydin Island where Gulf beauty shines then come back to enjoy more of everything this premiere Florida paradise offers.

Find Your South Naples Rental

Featured Property

Luxurious Condo in Aversana at Hammock Bay

Naples, Florida

3 Bdrms 3.25 Baths 6 Guests
From $178.57
per night + taxes & fees
View Details

Featured South Naples
Vacation Rentals

Your Local Team

Locally Owned and Operated In South Naples

Remember, 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.

Meet Sean, with 20 years in Medical Device and 8 years in semiconductor development, Sean’s expertise ensures top-notch service. A seasoned traveler, he’s passionate about creating unforgettable local connections through rental living. At SkyRun, we offer comprehensive management services and authentic vacation experiences for homeowners and guests. As a proud member of the South Naples community, we’re committed to being good neighbors and valued partners.

Sean Duggan

South Naples, FL

Owner of SkyRun Marco Island

Let's Talk!

3rd 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.

5th Avenue South

Upscale 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.

18th Avenue South Beach

Old Naples meets beachfront bliss. 18th Avenue South Beach’s laidback vibes equals a quieter beach day than some other Naples’ Gulf-front spots. Nearby restaurants let you grab a bite in between boogie boarding and sand castle building sessions.

Naples Beach

More 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.

Historic Downtown

Charm oozes out of this former fishing village. Stop at Palm Cottage, the oldest house in Naples. While history buffs can soak in Naples’ bygone eras, shoppers and culinary enthusiasts relish in the upscale shops and boutiques lining the streets. Leave the car behind–this walkable stretch gives you the chance to meander for ultimate exploration.

Keewaydin Island

Leave the car behind–this stretch of Gulf paradise is only accessible by ferry. Nature thrives here and you might spot turtles nesting next to your sandcastle masterpiece. This island makes the ideal escape for sun lovers wanting a break from the Naples crowds. Remember to pack everything you need–this is a retail-less stretch.

Naples Bay

Kayak or paddleboard your way through Naples Bay’s waterways. Charter a tour to spy dolphins and manatees at home in these calm waters. Obviously this is a haven for fishing–grab your pole! Cap off your day as you watch the sun close another day in paradise aboard a sunset cruise.

Florida Everglades

Think Florida and you’re likely to agree the Everglades are a  must-see. Stop at the  Gulf Coast Visitor Center and then explore the park’s Gulf Coast area, whether by boat tour, ranger-led programs, or self-guided hiking trails. Hike Big Cypress’ Loop Road for birdwatching. Kayak or boat through Ten Thousand Islands’ mangrove maze to spot manatees, dolphins, and diverse wildlife that make your Everglades escape one for the vacation books.

Marco Island

Marco Island’s pristine beaches, abundant wildlife, and vibrant culture offer the ideal balance of fun and relaxation. Swim Tigertail Beach, explore the Everglades, or indulge in art and shopping at Marco Walk Plaza. 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 the island with life.

Bark of the Ark

Pure 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.

Explorers

Rising 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.

Naples Zoo

Whether 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.

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.

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.

Extreme Boat Rentals in Naples

Discover hidden coves, race across the waves, and explore the Gulf of Mexico like never before.

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.

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.

Cruisin Tiki’s

Floating fiesta that blends the charm of a tiki bar with the beauty of Naples’ coastal scenery.

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.

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.

Naples Botanical Gardens

Paradise 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.

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.

Artis-Naples

Artis-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.

Get Outdoors

Birders, 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 Wellness

Grab 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.

What To Expect

As local residents, SkyRun staff are available to help you make the most of your trip to Marco Island.  We strive to have your property ready with everything you need and to provide you with all the information you will need even before you have to ask for it.

But if you DO need something, our staff are here to help daily (and on call 24/7 for emergencies).  We communicate with you the way YOU want to communicate.  That can be using our webchat or simply giving us a call. We’ll also be sending you a few emails before and during your stay with important information. You can also text us via our industry exclusive 2-way text messaging system.

Included Services

  • Pre-arrival quality inspection
  • Pool/ Hot tub maintenance (as applicable)
  • Most properties have free parking (check each property listing for possible charges)
  • Luxury linens & towels
  • Fully equipped kitchens
  • Wi-Fi and TV’s
  • Departure cleaning and trash removal

Starter Supplies

  • Salt, pepper and cooking oil
  • Coffee and coffee filters
  • Garbage bags
  • Dish/Dishwasher and laundry detergent (as applicable)
  • Hand soap and lotion
  • Shampoo and conditioner
  • TP, paper towels and tissue
  • Hairdryer and ironing board

Check-In Instructions

Check-in is 4:00pm ET and check-out is 10:00am ET. A check-in instructions email will be distributed to guests 7 days prior to arrival date containing directions and access information for the property. In most cases guests will access a property via a lockbox or smart lock using the given access code. Early check-ins can only be confirmed on the day of arrival.

Guests must depart the property by the check-out time unless a late checkout has been coordinated and confirmed with the SkyRun office. Late check-outs must be coordinated directly with the SkyRun office no later than 9am on the day of departure; please note that if we have an incoming guest we will not be able to accommodate a late checkout. We ask that guests remove major trash from the unit, return the furniture to it’s original location, load and run the dishwasher, set the thermostat to 78 degrees, turn off all lights and lock doors.

Parking

Parking may be limited. The check-in instructions email will contain information regarding parking at your property. Any parking fines assessed to your vehicles during your stay will be billed to you if they are billed to us.  Parking fines can be significant.

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.

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 been wonderful to work with. They are very forthcoming and professional. The team does an outstanding job taking care of both property owners and guests alike.

UliSarasota, 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

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Marco Island Frequently Asked Questions

SkyRun provides photos, virtual tours, 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.

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 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.

When you book direct with SkyRun you avoid paying service fees that traditional listing sites like Airbnb and Vrbo charge. 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.  We also offer a fantastic value on lodging booked within 30 - 60 days of arrival with our dynamically adjustd rates.

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 booked with a 3rd party booking site. You can also add travel insurance onto your reservation within 48 hours of booking with SkyRun. 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 can not cancel your reservation for any reason.  If you have travel insurance and need to cancel or make a claim refer to your specific policy. More information about the travel insurance policies SkyRun offers can be found here.

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. 30 days before your arrival, the remaining amount is due and becomes non-refundable if you need to cancel for any reason (see travel insurance above for exceptions).  At this time, the credit card we have on file will be automatically charged for the balance.

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.

No smoking and no pets (unless specifically designated as a pet-friendly property) are allowed in the rentals.  House parties and exceeding the maximum occupancy at any time are prohibited. 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.

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