Jacksonville Vacation Rentals Carve out a slice of paradise with one of Jacksonville’s best rentals Where Florida Jacksonville - 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 Jacksonville Properties USA > Florida> Jacksonville Visit Jacksonville Arts and culture, sport and sand, beaches and sun. Visiting Jacksonville means you don’t have to choose. Have all the adventure and relaxation you crave when you hit Jacksonville Beach to get that vitamin D hit. Speaking of hits, Jacksonville hosts the Jacksonville Jaguars Iceman minor league hockey and the minor league baseball’s Jumbo Shrimp. Arts lovers flock to the Museum of Science and History (MOSH) and the Cummer Museum. Since this is Florida, the fishing, golfing, and outdoor way of life infuse the area with ample opportunities for fitness and fun under the sun. Your Jacksonville Vacation, Your Way.Exceptional ViewsGood for GroupsFamily Friendly Find Your Jacksonville Rental New Property Courtney Woods Oasis Jacksonville, FL 3 Bdrms 2 Baths 8 Guests Pet Friendly View Details Search while moving Your Local TeamLocally Owned and Operated In JacksonvilleRemember, 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. Mike M.Jacksonville, FLOwner and Operator904-440-1500jacksonville@skyrun.comLet's Talk! Beaches and Areas to Explore Things to Do Dining Property Damage Waiver Travel Insurance Check-In Instructions Riverside/Five PointsStroll the Riverside/Five Points neighborhood and the city’s vibrancy comes alive. Jacksonville mainstays like the Riverside Arts Market, the Cummer Museum of Art and Gardens, and plenty of boutiques and shops round out this hotspot’s offerings. Jacksonville BeachThe most popular and lively of the local beaches, Jacksonville Beach features a long fishing pier, great surfing spots, beach bars, and a walkable strip of restaurants and shops. It’s ideal for visitors looking for an energetic beach day with plenty to do. Downtown JacksonvilleThe Riverwalk winds through downtown Jacksonville and is lined with places to see and be seen as well as quieter spots that highlight the city’s natural wonders. Make sure to leave time to visit the Museum of Science and History and check out the bustling dining scene the area is known for. The Jacksonville Beach PierThe Jacksonville Beach Pier is a must-visit spot for ocean lovers, offering stunning sunrise views, scenic strolls, and some of the best fishing in the area. Stretching over 1,300 feet into the Atlantic, it’s perfect for catching waves, casting a line, or simply soaking in the sea breeze. With restaurants, surf shops, and beachside entertainment nearby, it’s the ideal way to spend a laid-back Florida day. Atlantic BeachJust north of Jacksonville Beach, Atlantic Beach is a quieter, more residential stretch of sand with wide beaches, gentle waves, and cozy local dining. It’s great for families, casual surfers, and anyone looking for a more laid-back experience. Neptune BeachBordering Atlantic Beach, Neptune Beach offers a similarly relaxed atmosphere with a hip, small-town vibe. Centered around the Beaches Town Center, it’s walkable and full of boutique shops, craft coffee, and casual dining right near the ocean. Ponte Vedra BeachUpscale and serene, Ponte Vedra is known for its beautiful dunes, golf resorts, and luxury homes. It’s perfect for those seeking a more refined beach experience or a romantic getaway with nearby spa and golf options. FishingCome and try your luck where the St. Johns River and Atlantic Ocean meet. The Intracoastal Waterway’s marshes and creeks teem with fish like trout and flounder. Flounder and redfish also abound at Nassau Sound and if you want to venture into the Atlantic, you could be rewarded with wahoo, amberjack and mahi mahi. Want to find the best waters to cast your line? Fresh and saltwater charters take you to the hottest spots. GolfObviously the Florida weather means year-round golf, but it’s not just the sunshine that keeps golfers on the links–after all, this is home to the PGA Tour Headquarters. Golfers and tee off at public and private courses. Standouts include TPC Sawgrass and World Golf Village, but public courses like Jacksonville Beach Golf Club and Hyde Park Golf Club invite guests to book tee times. Twilight discounts and special packages let you golf Jacksonville at discount prices. Horseback RidingDon’t count out Jacksonville when it comes to saddling up and hitting the trails. The area’s equine offerings like Diamond D ranch. About a 25 minute drive from Jacksonville, Diamond D offers trail rides ranging from 1-4 hours and even horse camp for kids in the summer. Kayaking & Paddleboarding Explore Jacksonville’s scenic waterways with easy access to self-serve kayak and paddleboard rentals at spots like Castaway Island Preserve and Mandarin Park via the PADL app. For guided experiences, Adventure Kayak Florida offers eco-tours through marshes, lakes, and even full-moon paddles. It’s a peaceful and immersive way to see local wildlife and hidden natural gems. River Tours & TaxisHop on the St. Johns River Taxi for a fun, scenic way to explore downtown Jacksonville’s waterfront. They offer eco-tours, sunset cruises with live music, and stops at local dining spots. It’s a low-key, family-friendly way to experience the city from a unique perspective. Boat RentalsRent a powerboat, pontoon, or sailboat through platforms like Boatsetter to cruise the St. Johns River or Intracoastal Waterway. Rentals are available by the hour, with or without a captain, making it easy to plan anything from fishing trips to fun group outings. Perfect for travelers who want freedom to explore at their own pace. Matthew’s Restaurant – San MarcoFor a special night out just minutes from downtown, Matthew’s is your go-to. This refined spot serves up seasonal, creative American fare in an upscale setting—perfect for a romantic dinner or celebratory meal. Palms Fish Camp – Heckscher DriveIf you’re up for a short drive/ride, Palms Fish Camp delivers fresh local seafood with unbeatable views. Set on the water beneath the oaks, it’s a relaxing, locals-approved spot for oysters, cold drinks, and river breezes. Orsay – Riverside/AvondaleTucked in a charming historic neighborhood, Orsay brings French bistro vibes to Jacksonville. It’s cozy, classy, and perfect for brunch with friends or a date night with steak frites and wine. The Bearded Pig – San Marco & Jax BeachWhether you’re downtown or near the beach, The Bearded Pig is barbecue heaven. Brisket, ribs, and Southern sides meet a chill, beer garden vibe that’s perfect for casual dining and good company. 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 nonrefundable. 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 Check-In: Check-in is 4:00 p.m. CT. Seven days prior to the arrival date, guests will receive an email that contains directions and access information for the property. In most cases, guests will access a property via a lockbox or smart lock using an access code. Early check-ins can be confirmed only on the day of arrival. Check-Out: Check-out is 11:00 a.m. CT. 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 9 a.m. 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 its original location, and load and run the dishwasher. 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 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 Matt was very clear from the start and helped us build real expectations for our investment property. We’re pleased with how easy the process has been. Paul & ClaireBradenton, 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 Jacksonville Blog New SkyRun Location Opens in Jacksonville, FL Read More View All Explore Nearby Areas Micro Market 2Micro Market 3 Jacksonville 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? 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? Yes! You are getting the guaranteed best rates on our rentals when you book direct. By booking with us instead of through a third party listing site like Airbnb or Vrbo, you avoid paying additional service fees and therefore will get the lowest rates possible on our rentals. 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 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. Ask us for more information about the travel insurance policies SkyRun offers. 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. 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. 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
Explore Jacksonville’s scenic waterways with easy access to self-serve kayak and paddleboard rentals at spots like Castaway Island Preserve and Mandarin Park via the PADL app. For guided experiences, Adventure Kayak Florida offers eco-tours through marshes, lakes, and even full-moon paddles. It’s a peaceful and immersive way to see local wildlife and hidden natural gems.
