St. Augustine Vacation Rentals Condos and single family homes for the ideal St. Augustine getaway Where Florida St. Augustine St. Augustine Beach St. Augustine Beach South Town of St. Augustine - 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 St. Augustine Properties USA > Florida > St. Augustine Visit St. Augustine Come for the water and what the Florida sunshine offers, but prepare yourself–-St. Augustine isn’t just another shorepoint. As the oldest continuously habited US city, clearly history thrives alongside the sand, sun, and surf. Visit Castillo de San Marcos, the masonry monolith the Spaniards built as they settled the area. Maybe you want to partake in the Fountain of Youth just like Ponce de Leon did more than 500 years ago. History lives here, but St. Augustine thrums with a vibrant dining scene, almost unlimited water adventures like fishing, surfing, and kayaking, and plenty of stops that appeal to all ages. Whether you’re here for a long weekend or an extended stay, you’ll be charmed by this Florida gem. Your St. Augustine Vacation, Your Way.Pet FriendlyBeach AccessFamily Friendly Find Your St. Augustine Rental Featured Property Nocatee Family Oasis Ponte Vedra, FL 3 Bdrms 2 Baths 8 Guests Pet Friendly From $225.00 5.0 per night + taxes & fees View Details New PropertyFeatured Property Historic Hideaway Gem - Games and Wine Included with Booking! St Augustine, FL 3 Bdrms 2 Baths 8 Guests Pet Friendly From $145.00 5.0 per night + taxes & fees View Details Serenity Shores - Games and Wine Included with Booking! St Augustine, FL 2 Bdrms 2 Baths 4 Guests Pet Friendly From $100.00 5.0 per night + taxes & fees View Details Search while moving Featured St. AugustineVacation Rentals From $225 / night Nocatee Family Oasis Ponte Vedra, FL 8 Guests 3 Bdrms 2 Baths From $145 / night Historic Hideaway Gem - Games and Wine Included with Booking! St Augustine, FL 8 Guests 3 Bdrms 2 Baths Your Local TeamLocally Owned and Operated In St. AugustineRemember, 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. Randy is an accomplished business executive with over 20 years of experience in crafting and implementing engagement strategies that boost sales and revenue. A strong advocate for community support, Randy is thrilled to launch SkyRun in the St. Augustine market. His mission is to deliver exceptional property management services, ensuring guests enjoy the vacation of a lifetime in St. Augustine. Residing in St. Augustine with his wife, kids, and two dogs, Randy is deeply rooted in the local community. When he’s not working, you might find him volunteering, exploring the state, having fun with his kids, or relaxing by the pool with a grill and his beloved dogs. Randy RingpfielSt. Augustine, FLOwner of SkyRun St. Augustine Let's Talk! Beaches Things to Do What To Expect Check-In Instructions Property Damage Waiver Travel Insurance St. Augustine BeachPark your favorite beach chair in the sand and let the Florida rays melt your cares away. St. Augustine Beach invites locals and visitors to play in the waves, which tend to be gentler for novice surfers. Cast off from the St. Johns County Ocean Pier Park, which features the perfect place to fish, play at the volleyball courts or kids’ splash pad, and access the beach for free. Pack your own beach gear or rent umbrellas and more from one of the beach’s rental companies. Anastasia State ParkWander through and delight in the more than 1,600 acres of beach, tidal marshes, and dunes at this Florida State Park treasure. Salt Run plays host to birds foraging for food, and watch for eagles and ospreys overhead! Kayak, canoe, and bike around the beach with rentals available at the concession building. If you reel in a big catch, the park’s fish-cleaning station is an added convenience. Vilano BeachJust north of St. Augustine sits local favorite Vilano Beach. Even getting to Vilano Beach provides ocean views aplenty when you drive the A1A or cross the water from St. Augustine on the Dolphin Bay Scenic Shuttle, a passage that opens up chances to watch dolphins play and birds scout for fish. Fish from the pier or launch your boat to go into deeper water. Don’t miss the beach’s restaurant and the iconic Blue Bird of Happiness statue. Butler BeachThe white sands of Butler Beach beaches summon those looking for seaside therapy and for those looking to explore history. Frank B. Butler, an African American man living in the early 1900s, became enraged by the segregation implemented at Florida’s beaches and decided to buy the tract of oceanfront now named for him. Today, Butler Beach’s pavilions, grills, and free parking invite everyone to enjoy this seaside delight. Crescent BeachCrescent Beach gets its name from the C-shape of its shoreline that hugs the Atlantic and tends to be one of the area’s quieter spots. This family-friendly coastal getaway provides ample parking, gazebos, and dunes to explore. Check out this ocean locale for an Old Florida vibe. Ponte VedraCome and see why CNN named this St. Augustine spot one of its 22 Can’t Miss Beaches in the US. Why? Maybe it’s the 15-foot Ponce De Leon statue or the beaches dotted with shark teeth that treasure hunters can source. Parking and leashed dogs round out this picture-perfect shorepoint. Mickler’s Landing Local tip: say Mike-ler’s Beach to blend it with the locals and bask in this pink-sand escape. A walkway winds you through 20-foot dunes and opens up to a natural marine escape. Spot marine wildlife as you soak in the sun. Parking makes this an easy stop and leashed dogs are welcome. BikingThree can’t miss trails for bikers–Anastasia State Park,Vilano Beach Causeway,St. Augustine Beach Boardwalk, and Matanzas Riverwalk. Anastasia State Park’s four miles of sandy beaches and roads winding in the park invite bikers to ride along the coast and explore. If you want your ride with a side of sweeping ocean views of the Vilano Beach Causeway’s bike lane connects riders from St. Augustine to Vilano Beach with views of the Atlantic and St. Johns River along the way. Walkers, runners, and bikers all hit St. Augustine Beach Boardwalk for its views of the Atlantic and fun, flat paths. St. Augustine also features bikeable lanes throughout town if you want to ditch the car. FishingThe Gulf Stream makes St. Augustine an angler’s paradise with waters teeming with marlin, salmon, and grouper. In fact, certain charters target specific kinds of fish to hone in on to score a big catch. Grab a kayak, boat, or canoe for inshore and backwater fishing along the The Matanzas River, The Intracoastal Waterway, The Salt Run, and The Tolomato River where the trout, redfish, and flounder bite. Whether you set off along the St. Johns River or head out on the Atlantic, you can curate the perfect fishing experience. GolfThe sun is shining and the links are calling! Worldwide, Florida stands out for the numerous golf courses dotting the state, and the St. Augustine area summons golfers to tee off. The World Golf Hall of Fame offers two courses–King & Bear and Slammer & Squire–that give golfers the experiences of an open, links-style layout as well as traditional Florida courses peppered with natural elements that bring golfers closer to nature. Ponte Vedra Inn and Club’s Ocean and Lagoon Courses stand out and have been hosting golfers since 1928. The par-71 Ocean Course features expansive fairways and new green complexes. The Lagoon Course meanders through waterways and stands at par-70. Head over to The Golf Club at South Hampton, a public course offering a laid-back vibe to enjoy the game. It doesn’t get more luxurious than Hammock Beach’s two courses that earned Golfweek’s 2020 Top 100 Resort Courses. Simply put, you will find whatever course suits your game when you visit St. Augustine. The Fountain of Youth Archaeological ParkWe in 2023 may have plentiful anti aging potions, but the desire to stay young is nothing new. The Fountain of Youth Archaeological Park tells the story of Juan Ponce de León, who in 1513 took to the springs in his attempt to combat aging. You, too, can drink from the spring and see if you notice any benefits. The spring’s park also highlights the history of the Timucuan, who first lived on the land. Water AdventuresSurfers catch waves at Vilano Beach, Crescent Beach, and St. Augustine Beach, especially in the fall and spring when the waves heighten and the thrills heat up. Take a lesson at one of the area’s surf schools and test out your new skills on the Floridian waves. Kayakers have no shortage of waterways to explore, whether it’s on the ocean or on the river. Head out on your own or book a tour. If being on the water isn’t enough, take to the skies when you parasail over the beach, the Matanzas River, or the Intracoastal Waterway and catch stunning marine views. Add snorkeling and dolphin adventures that get you up close to these amazing marine creatures, and you could spend your entire St. Augustine stay waterside. Dining and NightlifeSt. Augustine hosts Florida’s oldest dining hub, the Columbia Restaurant. Since 1905, this St. Augustine hallmark has tempted diners with Cuban and Spanish-inspired dishes that patrons enjoy in a space outfitted with lush palms and grand archways. Of course sitting on the water means that many spots serve the freshest catches to satisfy the seafood enthusiast. Not every spot is upscale–plenty of cafes, casual eateries, and a growing brewery and wine scene means that you can mix your menu up during your stay. Arts & CultureNo stranger to the arts, St. Augustine’s cultural spots make this Florida city more than a typical oceanside stay. St. Augustine Amphitheatre–but call it The Amp like the locals do–is a 4,000-set outdoor amphitheater that has entertained past guests with concerts from Florida legend Jimmy Buffet, Bruch Springsteen, and other international acts. Book your ticket for an evening of musical fun. If you tour the Lightner Museum and find yourself feeling a New York state of mind, it’s not just you–Henry John Hardenbergh can add this Florida hotel-turned-museum to his other projects like NYC’s Plaza Hotel. The museum’s highlights include Victorian antiques, historic mechanical musical instruments (including a 17th-century Stradivarius violin), and the popular Tiffany glass exhibition. The Moorish-style Villa Zorayda is a former mansion and now a museum that showcases Spanish and Moorish design and hosts events throughout the year. ShoppingAmble along the cobblestones lining St. George Street, the country’s oldest continuously inhabited street and take in shops and restaurants that bring this area into the modern day. Everything from souvenirs to art to antiques make St. George Street both a historical can’t-miss and a retail therapy destination. Heritage Walk’s outdoor footprint means that you can pop in and out of national chains to score the latest finds. Bargain hunters can find deals in two outlet centers–St. Augustine Premium Outlets and Tanger Outlets St. Augustine and vintage lovers can try their luck at the Anastasia Flea Market and the St. Augustine Flea Market. Castillo de San MarcosStart with Castillo de San Marcos, the US’ oldest masonry fort erected when Spain laid claim to Florida. Today, the National Park Service has taken over and invites visitors to meander through the dungeons, barracks, and passages. Take part in the fort’s ranger program called “Canning and Firing” where you can learn how cannons were used for warcraft in the 18th century. You can also explore at your own pace with the National Park Service app that fills visitors in on the monument’s rich history. St. Augustine Lighthouse and Maritime MuseumAnother testament to the area’s history is the St. Augustine Lighthouse and Maritime Museum, displaying the nation’s oldest lighthouse. Climb the 165 feet to the top or explore the museum’s hands-on activities like the Shipyard Playground and Heritage Boat Works’ activities dedicated to sustaining wooden boat building today. The Maritime Archaeology and Education Center takes people back to 1737 with its lighthouse history. These features and more make this a must-add stop to your St. Augustine tour. St. Augustine Shipwreck MuseumArrrghhh…come and learn about pirates’ booty lost to the seas! Shipwreck tours, prizes, and artifacts from The S.S. Central America, The Nuestra Señora de Atocha, and even the R.M.S. Titanic take modern explorers on a maritime journey through the past. An art gallery and store round out this treasure hunt. St. Augustine Alligator Farm Zoological ParkGet up close (but not too close) with more than 24 species of crocodiles and other wildlife at this exhibit that has been dazzling locals and visitors since 1893. Come see all stages of crocodilian life from hatchling to adult and take in the more than 2,000 alligators and crocodiles at the park. Educational activities, exhibitions, and animal shows educate and entertain, and the facility’s wetland education means that you can walk away with knowledge not only about these fascinating Florida creatures but also the habitats in which they live. What To Expect As local residents, SkyRun staff are available to help you make the most of your trip to Florida. 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 Snow removal 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 laundrty 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 EST and check-out is 10:00am EST. 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, 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 SkyRun. Please be aware, parking fines are unnecessary and 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 St. Augustine 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 Orlando Micro Market 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? 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 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. 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. 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. 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. 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