Experience Island Luxury with AMI Locals. Whether you’re planning a romantic escape, a refined family retreat, or a sophisticated group getaway, our luxury Anna Maria Island vacation homes place you just steps from powder-soft beaches, exceptional dining, and the island’s most coveted experiences—all while offering the refined amenities and personalized touches of a world-class coastal stay.
Beach Hideaways to Grand Estates
-
Our 1–2 bedroom Anna Maria Island vacation rentals are an ideal choice for couples, friends, and small families ready to book a relaxed yet refined island getaway. These beautifully appointed homes offer comfortable, stylish living spaces and are perfectly located near Anna Maria Island beaches, Holmes Beach, and Bradenton Beach. With top-rated dining, local shops, and favorite island attractions just moments away, everything you need for an effortless coastal stay is right at your fingertips.
Learn More
-
Our 3–4 bedroom Anna Maria Island vacation rentals offer an elevated island experience for families and small groups seeking space, comfort, and effortless style. These thoughtfully designed homes feature multiple bedrooms and generous living areas, ideally located near Anna Maria Island beaches, boutique shopping, and celebrated local dining. It’s the perfect setting to unwind, reconnect, and enjoy island living at its finest.
Learn More
-
Experience the perfect blend of luxury, space, and comfort in our 7+ bedroom Anna Maria Island vacation rentals — ideal for large groups and multi-generational families. Each high-end home offers expansive living areas, private pools, and resort-style amenities designed for unforgettable group vacations, family reunions, and beach getaways. Conveniently located near Anna Maria Island’s best beaches, upscale dining, and top attractions, these luxurious rentals provide everything you need for an exceptional island experience.
Learn More
-
Experience the perfect blend of luxury, space, and comfort in our 7+ bedroom Anna Maria Island vacation rentals — ideal for large groups and multi-generational families. Each high-end home offers expansive living areas, private pools, and resort-style amenities designed for unforgettable group vacations, family reunions, and beach getaways. Conveniently located near Anna Maria Island’s best beaches, upscale dining, and top attractions, these luxurious rentals provide everything you need for an exceptional island experience.
Learn More
Showing: 5 specials
Specials
America’s 250th Birthday
Celebrating long weekends, coastal traditions, and time well spent, honoring America’s 250th with Prime Vacations. We’re inviting guests to share their favorite vacation memories and traditions for a chance to win our America 250 Grand Prize.
*Terms and Conditions Apply. Please see contest page for full details and how to enter.
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.