If you are having difficulty finding the dates and pricing you are looking for, please call our office for assistance at (800) 544-4593. Our reservation specialists will be happy to assist you in planning your vacation to our Nation's Oldest City. Thank you for choosing MAY Realty & Resort Rentals for all your travel needs.

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  1. OSR 104

    This 2 bedroom, 2 bathroom, first floor Ocean Sunrise condominium is spacious and immaculate and comes with reserved parking. Amenities include private beach access, pool, washer/dryer, private lanai, gated community, covered parking, and much more. Master bedroom has French doors, which open to large master suite with king size bed. Guest bedroom has two twin beds and living room offers a sleeper sofa. Televisions in living room and master bedroom. Fully equipped kitchen including dishwasher and microwave. Vacation staples available within this condominium community include a heated pool, tennis and private beach access. The breathtaking views of the Atlantic Ocean from the patio are enough on it’s own to draw you to this Ocean Sunrise condo. Looking out over the beautifully landscaped property you’ll see the gorgeous dunes leading up to the white sandy beaches of St. Augustine’s Anastasia Island. Waking up to the sea salt breeze and listening to the waves crash as the sun rises is a view too good to pass up! Play Tennis on the courts of St. Augustine Beach or go golf at the many courses the First Coast has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • Ocean Front
    • Flat
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    OSR 104
    St. Augustine FL
  2. OVC F-17

    This nicely decorated, 2 bedroom 2 bath, ground floor, poolside condo in St. Augustine Beach’s Ocean Village Club. A beautiful gated community of St. Augustine condo rentals on St. Augustine Beach, Ocean Village Club amenities include a clubhouse, two swimming pools (one heated), two tennis courts, four shuffleboard courts, a picnic area with grills, and a private beach walkway. In the clubhouse there is an exercise room, library, PC for guests' use, flat screen TVs, and wireless internet. The upstairs activity room in the clubhouse includes a full kitchen and 2 decks. Master bedroom features queen size bed. Guest bedroom offers two twin beds and a sofa sleeper in the living room. In-unit washer and dryer. Kitchen is fully equipped including dishwasher and microwave. This is a pet friendly condo. You’ll be just a short walk to both the Atlantic Ocean and the beautiful Matanzas River/Intracoastal Waterway. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • Pool View
    • Flat
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    OVC F-17
    St. Augustine FL
  3. PI 133E

    This 2 bedroom, 2 bathroom condo located in the Pelican Inlet complex that is right on the Intracoastal Waterway/Matanzas River. Amenities include a dedicated laundry room, breakfast bar, dishwasher, private lanai, high-speed Internet, a reserved parking space, and much more. The master bedroom features a Queen bed with its own master bathroom and a sliding door out to the lanai. The second bedroom features an “under-the-sea” décor that the kids will love and has two twin beds. The Pelican Inlet complex is friendly and beautifully maintained and features a large swimming pool surrounded by lounge chairs offers great entertainment and two private tennis courts. The Pelican Inlet community has a great family atmosphere with an on-site boat ramp and a private walkway across the street leading right down to Crescent Beach. This rental is only available from September 1st to May 30th. You’ll be just a short walk to both the beautiful Matanzas River/Intracoastal Waterway and the Atlantic Ocean. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • St. Augustine Beach
    • Flat
    • Sleeps 4
    • 2 beds, 2 bathrooms
    • View Details
    PI 133E
    St. Augustine FL
  4. SO 6

    This direct oceanfront two bedroom, two bathroom condominium at Sea Oats Villas is right off A1A Beach Boulevard, located in the heart of St. Augustine Beach. This second floor condo offers many amenities including DVD player, televisions, washer and dryer, fully equipped kitchen, linens, a private screened balcony facing ocean and a private walkway for beach access. Master bedroom features king size bed and guest bedroom offers two twins. Living room has full sleeper sofa. Open the sliding glass door and enjoy the fresh salt air on the patio that feels almost like its part of the dunes! The low key design and wonderful views will draw you in, and the beautiful lawn leading right up to the walkway over the dunes will make you never want to leave! A1A Beach Boulevard runs parallel to St. Augustine Beach and features great shopping, many restaurants offering a variety of cuisines, St. Augustine’s fishing pier and a number of great beach activities. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • Ocean Front
    • Flat
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    SO 6
    St. Augustine FL
  5. SP 12233

    From this ocean-view 2 bedroom, 2.5 bath two-story townhouse at St. Augustine Beach’s Sea Place complex, you can feel the sea breeze and fall asleep to the Atlantic Ocean surf. The Sea Place complex is right off historic Butler Beach on A1A South conveniently located in the center of all that Anastasia Island has to offer: great restaurants, shopping, water sport rentals, great fishing, beautiful beaches, and much more. This rental is fully upgraded and nicely decorated with two televisions in living room and master bedroom. Master bedroom features a king bed and the guest bedroom has a queen bed. Wireless internet is provided. The Sea Place complex is oceanfront with two swimming pools, a jacuzzi, multiple private tennis courts, racquetball courts, and a private walkway to the beach. The courtyard and large sunbathing area around both pools offers space to relax and watch both the sunrise and sunset from your lounger. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • Ocean View
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    SP 12233
    St. Augustine FL
  6. SP 14251

    From this ocean-view 2 bedroom, 2.5 bath two-story townhouse at St. Augustine Beach’s Sea Place complex, you can feel the sea breeze and fall asleep to the Atlantic Ocean surf. The Sea Place complex is right off historic Butler Beach on A1A South conveniently located in the center of all that Anastasia Island has to offer: great restaurants, shopping, water sport rentals, great fishing, beautiful beaches, and much more. The master features a king bed while the second bedroom has two twins. The living room has a pull out sofa for extra guests (unit sleeps 6). Linens, towels are fully stocked. There are TVs in all bedrooms and the unit has free wireless Internet. The Sea Place complex is oceanfront with two swimming pools, a jacuzzi, multiple private tennis courts, racquetball courts, and a private walkway to the beach. The courtyard and large sunbathing area around both pools offers space to relax and watch both the sunrise and sunset from your lounger. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • Saint Augustine, FL
    • Ocean View
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    SP 14251
    Saint Augustine FL
  7. SP 14260

    From this pool-side, ocean-view 2 bedroom, 2.5 bathroom two-story townhouse at St. Augustine Beach’s Sea Place complex you can feel the sea breeze and fall asleep to the Atlantic Ocean surf. The Sea Place complex is right off historic Butler Beach on A1A South conveniently located in the center of all that Anastasia Island has to offer: great restaurants, shopping, water sport rentals, great fishing, beautiful beaches, and much more. The master features a queen bed while the second bedroom has two twins. The living room has a pull out sofa for extra guests (unit sleeps 6) and the unit has both a washer and dryer for laundry. Linens, towels are fully stocked. There are TVs in all bedrooms and the unit has free wireless Internet. The Sea Place complex is oceanfront with two swimming pools, a jacuzzi, multiple private tennis courts, racquetball courts, and a private walkway to the beach. The courtyard and large sunbathing area around both pools offers space to relax and watch both the sunrise and sunset from your lounger. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • Saint Augustine, FL
    • Ocean View
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    SP 14260
    Saint Augustine FL
  8. SP 15275

    From this beach front 2 bedroom, 2.5 bathroom two-story townhouse at St. Augustine Beach’s Sea Place complex you can feel the sea breeze and fall asleep watching and listening to the Atlantic Ocean surf. The Sea Place complex is right off historic Butler Beach on A1A South conveniently located in the center of all that Anastasia Island has to offer: great restaurants, shopping, water sport rentals, great fishing, beautiful beaches, and much more. This beach-front property features an upgraded kitchen, a master bedroom with a king bed, and a second bedroom with 2 twin beds. There are TVs in all bedrooms and the unit has free wireless Internet. Linens, towels are fully stocked. The Sea Place complex is oceanfront with two swimming pools, a jacuzzi, multiple private tennis courts, racquetball courts, and a private walkway to the beach. The courtyard and large sunbathing area around both pools offers space to relax and watch both the sunrise and sunset from your lounger. This property is also a short drive from historic downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Play tennis on Anastasia Island or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • St. Augustine, FL
    • Ocean Front
    • Townhouse
    • Sleeps 4
    • 2 beds, 2.5 bathrooms
    • View Details
    SP 15275
    St. Augustine FL
  9. BFT 104

    As if the beach, the ocean and the clear blue sky are not enough, Barefoot Trace St. Augustine condo rentals offer a wide range of on-site amenities to turn your St. Augustine vacation into a resort-style escape. Enjoy a private walkway out to the beach and ocean, take a dip in our heated oceanfront pool, then retire to our clubhouse which features a game room with a full-size pool table, and a well-equipped workout room. Clubhouse privileges are included with all Barefoot Trace condo rentals. Barefoot Trace makes it easy to get around our beach community and St Augustine. Our condo rentals are accessible by twin elevators at the north and south ends of the condos. We also enjoy two private walkways to the beautiful white sands of St. Augustine’s coastline. Add covered parking, tropical landscaping, shuffleboard, a tennis court and clubhouse/fitness room and you’ve got everything you'll need for a great vacation. You will see the Atlantic Ocean the moment you walk into the unit. While at the resort pool or combing wide stretches of quiet Crescent Beach on St. Augustine’s Anastasia Island. Open-plan living is just the ticket for warm weather and family time. Complex wide wireless Internet available for a fee. Particular to this ocean front condo is an in-built wet bar. Come five o’clock, it’s a great addition to your ocean views and fully stocked kitchen. The open kitchen means your dedicated family chefs and bartenders remain part of the action ongoing in the living room and out on the balcony. This condo has two bedrooms and two bathrooms, with an extra trundle bed to make room for everyone. The master suite’s especially sweet, with a king-sized bed, ocean views and its own bathroom. The guest bedroom features two twin beds. Both rooms offer personal TV sets and plenty of storage in a dresser and closet. Nearby, St. Augustine is just five miles away. It’s an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Please inquire with us for restaurant or golf course recommendations. Covered parking keeps your car cool whenever you need it, and the resort complex even offers boat parking. Read more »
    • St. Augustine, FL
    • Ocean Front
    • Flat
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    BFT 104
    St. Augustine FL
  10. BT 217

    Your St. Augustine vacation awaits at The St. Augustine Beach and Tennis Resort, where you’ll find a wonderful range of rental accommodations with resort-style amenities. Take a stroll from your vacation rental down our private beach walkway to wide white sandy beaches you can even drive on, if you like. This 2 bedroom, 2 bathroom condo has access to a wide range of amenities, including gated condo entrances surrounded by lush landscaping and an on-site bus service to downtown St. Augustine. However, the best amenity of all? The sparkling waters of the blue Atlantic Ocean...just steps from your vacation rental. The Beach and Tennis Club Resort condo rentals in St. Augustine offer beautiful, private accommodations to provide a beachside vacation you’ll remember forever. Swim in one of two large pools or take a stroll from your rental down our private beach walkway to wide, white sandy beaches of St Augustine and see why so many people fall in love with the St Augustine lifestyle. Downtown St. Augustine is a must see, with its historic buildings, fort & famous St. George Street. Great restaurants abound, in town & at the beach. Don't miss the Alligator Farm just 1 mile up the road. The entire property has recently been renovated. Play Tennis on 10 Har-true courts or go golf at the many courses St. Augustine has to offer including those at World Golf Village, TPC Sawgrass, the St. John’s County Course, and many others for every playing level and price range. Lazy days or whatever pace you desire, excellent restaurants for every taste, nightly entertainment, locally or in town. Nearby, downtown St. Augustine is an ideal day trip no matter your group dynamic or interests. The city is known for its many historic charms, gorgeous port and Ponce de Leon’s famous Fountain of Youth. Football fans will love its proximity to Gainesville or to Jacksonville, and the excitement of Daytona Beach is nearby. Orlando and Disney World is just over a two-hour drive to round out any great family vacation. Read more »
    • Saint Augustine, FL
    • Ocean View
    • Flat
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    BT 217
    Saint Augustine FL
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904-461-5732 | ireyes@mayresort.com | http://mayresort.com | 5431 A1A South Suite 102, St Augustine, FL 32080