From intimate island escapes to spacious coastal retreats, Anna Maria Vacations offers a diverse collection of Anna Maria Island vacation rentals designed to suit every style of stay. Whether you’re planning a romantic getaway, a laid-back family beach week, or a group vacation with friends, our homes are thoughtfully located near the island’s beautiful beaches, local dining spots, and favorite island attractions. Browse our Anna Maria Island vacation rentals below and find the perfect place to settle in and start making memories.
The Perfect Fit for Every Stay
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Our 1–2 bedroom Anna Maria Island vacation rentals are perfect for couples, friends, or small families looking for a relaxed and affordable island escape. These cozy homes offer comfortable living spaces and convenient access to Anna Maria Island beaches, Holmes Beach, Bradenton Beach, local dining, and nearby attractions.”
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Our 3–4 bedroom Anna Maria Island vacation rentals are ideal for families and small groups who want extra space to unwind and enjoy island time together. With multiple bedrooms and easy access to the island’s beaches, shopping, and dining, these homes balance comfort, convenience, and laid back coastal living.
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Our 5–6 bedroom Anna Maria Island vacation rentals are designed for larger families and group getaways, offering plenty of room to spread out, relax, and reconnect. Located close to Anna Maria Island beaches, Holmes Beach, Bradenton Beach, dining, and island attractions, these homes make group vacations simple and enjoyable.
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Our 7+ bedroom Anna Maria Island vacation rentals are ideal for memorable group vacations, family reunions, and multi-family beach trips. Featuring spacious living areas and resort style amenities, these homes are conveniently located near the island’s most popular beaches, dining spots, and attractions.
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Specials
Last Minute Savings
Summer vacation just got easier to plan. A fresh selection of Florida Gulf Coast Vacation Rentals are now available with newly opened dates for summer travel. Book within 28 days of arrival and save 12% with promo code LASTMINUTE12. Limited availability. Prime locations. Reserve your Anna Maria Island or Siesta Key summer stay today!
*Terms and Conditions apply.
Extended Stay Discount
Extended Beach Bliss: 30+ Nights, 15% Off Your beach house, your home base—for a month or more. Looking for a long-term coastal escape? Book 30+ nights and get 15% off select homes with utilities included. From island cottages to spacious villas, enjoy the comfort of home and the beauty of the beach—on your schedule. Book online using promo code EXTEND15 at checkout or call us at 941-779-0733 to book directly with our Reservations team!
*Terms and Conditions apply
Military, First Responder and Teacher Discount
Sunshine, Service, and Savings on Florida’s Gulf Coast. Active duty and retired military members, first responders, and educators can enjoy 10% off select vacation rentals across Anna Maria Island, Siesta Key, and Lido Key. To receive the Hero’s Discount, reservations must be booked directly with our local Reservations team by phone at the time of booking so eligibility can be confirmed before your reservation is finalized. Discounts cannot be added, adjusted, or applied after a reservation has already been booked online or confirmed. Eligible Guests Include:
- Active Duty & Retired U.S. Military
- First Responders (Police, Firefighters, EMTs, Paramedics)
- Certified Teachers & Education Professionals (K–12 or Higher Education)
*Terms and conditions apply. Valid on select homes only. Verification required at time of booking.
Florida Resident Vacation Rental Discount
Florida residents are only a short drive away from paradise! Enjoy 10% off select vacation rentals on Anna Maria Island, Siesta Key, and Lido Key when you book directly with our Reservations team.
To qualify for the Florida Resident Special, reservations must be booked by phone and the discount must be applied at the time of booking. Because residency verification is required before confirmation, discounts cannot be added to existing reservations or applied after an online booking has already been completed.
Skip the third-party fees and book direct with our local team for the best value on your next Florida Gulf Coast getaway.
Call 941-222-2101 to book direct and save 10%.
*Terms and conditions apply. Valid Florida ID required at time of booking. Offer valid on select properties only.