An Extra Night of Vacation is Calling: Book a Fall Getaway to Anna Maria Island & Get 1 Night Free
You know that feeling on the last morning of vacation, when you’re finally relaxed and it’s already time to load up the car? This fall, we’re giving you a little more time before that moment arrives. Book four nights at one of our featured vacation rentals on Anna Maria Island and your fifth night is free.
That extra day is your chance to fully settle into island mode. Sleep in, take one more swim, catch one more Gulf sunset, or enjoy a day with absolutely nothing on the calendar. Here’s how the offer works, plus a closer look at the 8 homes that qualify.
How to Get Your Free Night on Anna Maria Island
The offer is simple: book 4 nights and get the 5th night free at any of the featured properties below, for stays now through November 15, 2026. Pick your favorite, then call our team at (941) 777-1105 to book. Reserving by phone lets us apply the free night to your stay and answer any questions about the home or your travel dates along the way.
Fall is a great time to make the trip. The pools are heated, humidity drops and temperatures cool down, and local favorites start returning to the calendar, like the Bradenton Public Market on Old Main Street every Saturday from October through May and the Bridge Street Market in Bradenton Beach on Sundays starting in November. Book your fall getaway today before availability runs out!
8 Fall Getaway Rentals You Can Book Today
Every home on this list has a heated pool, and most are tucked into quiet Northwest Bradenton neighborhoods a short drive from the Anna Maria Island beaches. That means more room to spread out without giving up your beach days.
Al’s Dream | Bradenton Beach
3 Bedrooms | 2 Bathrooms | Sleeps 6 | Steps from the Beach
Want to skip the drive entirely? Al’s Dream sits right across the street from the white sand at award-winning Coquina Beach. This recently renovated downstairs unit pairs Old South charm with new appliances and comfortable seating, and a heated community pool and patio give you a spot to cool off between beach trips.
Treasure Island | Bradenton
4 Bedrooms | 2.5 Bathrooms | Sleeps 8 | Private Pool & Hot Tub
Villa Treasure Island gives bigger groups close to 2,400 square feet in a quiet neighborhood with lake views. Renovated in 2021 and 2023, this home’s backyard is the real showstopper: a private heated pool and hot tub tucked under an oversized screened cage with two wide panoramic screens, so evening swims come without the bugs.
Seaside Memories | Bradenton
4 Bedrooms | 2 Bathrooms | Sleeps 8 | Heated Pool & Gaming Room
Newly renovated in 2025, Seaside Memories offers about 2,800 square feet roughly 10 minutes from the beach. Two living rooms mean nobody has to fight over the TV, and the air-conditioned gaming room is a perfect hangout for the kids (or the competitive adults). Outside, a heated pool overlooks the lake, and there’s plenty of beach gear waiting for your first trip to the sand.
Turtle Cove | Bradenton
4 Bedrooms | 2.5 Bathrooms | Sleeps 8 | Heated Pool & Movie Room
Turtle Cove is made for family fun. Along with a heated pool and lake views, this Northwest Bradenton home has a movie room and a pool room to keep everyone entertained. Anna Maria Island and downtown Bradenton are each about 10 minutes away, so beach days and nights out are both easy to fit in.
Villa Verde | Bradenton
3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool
Renovated in 2022, Villa Verde is about 10 minutes from the Anna Maria Island beaches and even closer to Robinson Preserve, where you can walk, bike, or kayak through more than 600 acres of nature. Back at home, the private heated pool has soothing water features and a sun shelf, and every bedroom has its own smart TV.
Florida Breeze | Bradenton
3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool
Located in West Bradenton’s Heron’s Watch community, Florida Breeze is just 3 miles from Anna Maria Island. This recently updated home centers on a private heated pool enclosed by a premium screen that keeps out even the tiny no-see-ums, so you can enjoy the backyard from morning coffee to evening swim.
Aqua Breeze | Bradenton
3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool
Aqua Breeze puts you right between the island and downtown Bradenton, about 15 minutes from the beaches. The large heated pool comes with an enclosed, covered patio for shady lounging, and the primary bedroom has a king bed, a large TV, and an en-suite bathroom with a walk-in shower.
Keyt’s Key | Palmetto
4 Bedrooms | Sleeps 8 | Private Pool & Hot Tub
Newly renovated Keyt’s Key features a heated outdoor pool with a hot tub and water views. Located between Anna Maria Island and I-75, it’s about a 25-minute drive to the beach and an easy home base for exploring more of the area.
Book Direct and Save Even More
Here’s a bonus: when you book directly with Island Dreams Realty, you can save up to 10% in fees compared to booking on sites like Airbnb and Vrbo. Pair that with a free fifth night and your fall getaway stretches even further.
You’ll also be working with our local team from start to finish. We know these homes and the island well, so whether you need help choosing the right rental or a dinner recommendation once you arrive, we’re just a phone call away. Learn more about why booking direct with our local team pays off.
Claim Your Extra Night This Fall
Your extra night of vacation is calling! Choose your favorite of the 8 homes above, then call us to book 4 nights and get the 5th free for stays through November 15, 2026. Want to see more options for future trips? Browse our full collection of Anna Maria Island vacation rentals and Bradenton vacation rentals.
Ready to stay a little longer? Give our team a call at (941) 777-1105 and let’s get your fall getaway on the calendar.
