With its locally loved restaurants, unique shops, coffee houses, candy and ice cream boutiques, entertainment, and vibrant beach-town atmosphere, Flagler Avenue is one of the most desirable areas of New Smyrna Beach. For buyers looking to own a property with short-term rental potential, location is key — and being within walking distance of Flagler Avenue puts guests just steps from the dining, shopping, entertainment, and beach access that make New Smyrna Beach such a popular destination. Win-San, Atlantic Plaza, and The Pelican are three condo complexes located within walking distance of Flagler Avenue and offer opportunities for buyers seeking a property in an area where short-term rentals are permitted. Their combination of rental potential and proximity to one of New Smyrna Beach’s most vibrant areas makes these communities worth considering for buyers looking to invest in the New Smyrna Beach market.
Thinking of Purchasing a Short-Term Rental Condo in New Smyrna Beach?
Contact Local Experts, Kate Rosenberg and Sam Dautzenberg – 407-342-7999.

Win-San 111 N. Atlantic Ave
With its smaller size and quaint, relaxed feel, Win-San is a hidden gem for a New Smyrna Beach vacation. With only 42 units, this complex offers a more intimate beach experience with beautiful views of the ocean overlooking the community pool and easy guest parking. Enjoy on-site grilling areas perfect for casual evening dinners with family and friends after a day in the sun. Win-San is a guest favorite, bringing repeat visitors back year after year.
With just a short walk to Flagler Ave., Win-San provides easy access to some of the best restaurants, coffee, and shopping in NSB. For those looking at New Smyrna Beach vacation rentals, oceanfront condos, beach rentals, or an investment property, Win-San offers an ideal combination of location, convenience, and local-charm. On-site management makes renting or owning a worry-free experience.
Why Win-San is ideal:
- Direct Beach Access
- Oceanfront Location
- Community Pool
- Assigned Parking
- Grilling Areas
- Smaller, Relaxed Complex
- Repeat Guest Favorite
- Highly Walkable to NSB favorites spots
- Great for Short Getaways
Love it this location? You could own here. Browse condos for sale, pending or recently sold below!


Atlantic Plaza (Oceania) 421/425 S. Atlantic Ave
Located just a couple of blocks south of Flagler Ave, Atlantic Plaza offers a unique boutique condo experience in the heart of New Smyrna Beach. With direct beach access and an ocean-front pool, this property is the perfect choice for a relaxing beach vacation. Guests can truly enjoy the best of both worlds…just steps to the beach and a short walk to Flagler Ave. with all it has to offer. Leave the car behind and experience staying in one of the area’s most convenient locations.
This unique condo-hotel experience combines the comforts and space of a condo with the convenience and feel of a vacation hotel. On-site property management and an established rental setup makes ownership at Atlantic Plaza a breeze.
What makes Atlantic Plaza ideal:
- Direct Oceanfront Location
- Beachfront Pool
- Walk to Flagler Avenue/Best of both worlds
- Boutique Feel
- Condo-Hotel Experience
- Vacation-Rental Friendly
- On-Site Grilling Areas
- On-Site Management with strong rental potential
Could you see yourself owning here? Browse condos for sale, pending, or recently sold.


The Pelican – 2401 S. Atlantic Ave.
The Pelican offers a resort-style vacation experience in New Smyrna Beach, making it a great choice for families, groups, and travelers looking for more space and flexibility. For those that enjoy various floor plans, great community amenities, a large expanse of beachfront, multiple pools and flexible staying options, The Pelican makes it easy to settle in and enjoy a beach getaway. Its established rental program and on-site rental services make rentals convenient for both property owners and guests. With one-, two-, and three-bedroom options, The Pelican is well-suited for family beach vacations, group getaways, extended stays, and seasonal escapes.
Located further south on Atlantic Ave, this condo offers a quieter, more relaxed beach setting while still being within easy reach of Flagler Avenue’s local dining, shopping, and entertainment. For families searching for a New Smyrna Beach vacation, spacious beach accommodations, oceanfront lodging, or a relaxing Florida coastal getaway, The Pelican offers the space, amenities, and location to make your stay special.
What makes The Pelican ideal:
- 600 Feet of Pristine Beachfront
- Two Oceanfront Pools
- Resort-Style Experience
- Multiple Floor Plans
- Established Rental Program
- Flexible Stay Options
- Great Community Amenities
- Great for Families & Groups
- Peaceful Beachfront Setting
- Strong Vacation-Rental Appeal
Ready to make this location your own? Browse condos for sale, pending, or recently sold.


Ready to Plan Your Vacation
Book your beachfront getaway within walking distance of Flager Avenue and all NSB has to offer.
Whether you’re planning to stay near Flagler Avenue or exploring another part of New Smyrna Beach, NSB Reality Team is here to help you experience the best of NSB and find your own perfect piece of paradise for your next beach vacation.
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