Discover exceptional luxury island vacation rentals organized by exclusive communities. From private beachfront enclaves to resort-style island neighborhoods, explore premium condos and villas designed for unforgettable stays. Browse by community to find the perfect blend of location, amenities, and island lifestyle tailored to your ideal getaway.
Anna Maria Island Condos and Communities
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Hunters Point is a distinctive and newly established community boasting eco-friendly single-family homes. These homes are designed to coexist with nature while ensuring utmost comfort, each producing sufficient power for its own needs. As Hunters Point grows, residents can look forward to a communal pool and other enticing amenities. Situated in Cortez, a stone’s throw from Anna Maria Island, this resort community immerses you in a classic fishing ambiance. Choose Hunters Point for one of the most innovative and eco-conscious vacation rental experiences.
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Marbella Villas is an exclusive community in Bradenton Beach on Anna Maria Island, Florida, where contemporary island living meets refined Mediterranean influence. Thoughtfully designed, featuring clean architectural lines, terracotta accents, and curated tropical landscaping that create a sophisticated yet effortless coastal aesthetic. With a tranquil, resort-like ambiance and a premier location just steps from the Gulf of Mexico, Marbella Villas offers a polished retreat for those drawn to modern luxury, understated elegance, and seamless beachside vacationing.
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Just across the bridge from Anna Maria Island, One Particular Harbour Margaritaville is an exclusive, private gated resort condo community offering a luxury getaway in a serene waterfront setting. These impeccably maintained, high-end units are nestled in a quiet residential area yet remain only a short mile from the island by car, bike, or on foot, making them ideal for travelers seeking peace and privacy without sacrificing convenience. Guests enjoy stunning water views and premium resort-style amenities, including a community pool, splash pad, and scenic nature walk, creating the perfect upscale rental for a refined coastal vacation.
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Located on the northern tip of Anna Maria Island, this stunning bayside property sits just one block from Pine Avenue, the vibrant heart of the City of Anna Maria. Bayside Bungalows offers an unbeatable location—just steps from the bay, shopping, top local restaurants, the Anna Maria City Pier, and the free island trolley. It’s the perfect home base for experiencing everything Anna Maria Island has to offer.
These beautifully remodeled vacation rentals feature fully equipped kitchens, bay views, a shared heated pool and sundeck, and classic Florida coastal charm. Designed with flexibility in mind, the property offers short-term stays and multiple units, making it ideal for families, couples, or groups who want to vacation together while still enjoying their own private space.
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Welcome to the peaceful beauty of Anna Maria Island, where The Coconuts offers a modern beachfront escape. Located right on the shore, the resort features vacation rentals from cozy one-bedroom condos to spacious two-bedroom units, all designed for comfort and easy island living. Wake up to the sound of waves, step onto soft sand, and enjoy the relaxed island pace. With its convenient location and stylish accommodations, The Coconuts is a perfect choice for a memorable Anna Maria Island getaway.
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North Beach Village is an upscale residential community on Anna Maria Island, featuring a variety of elegant architectural styles that reflect the island’s historic charm. Surrounded by lush, manicured landscaping, the neighborhood offers a calm, refined atmosphere that appeals to vacationers seeking a peaceful and sophisticated retreat. With its quiet, tree-lined streets and easy access to the island’s pristine beaches, North Beach Village provides a beautiful, private setting for those who appreciate relaxed, island-style living in a more exclusive location.
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Island Paradise is a beachfront condo building in Holmes Beach offering updated units, stunning ocean views, and a refreshing pool—perfect for your next Gulf Coast getaway. Located just steps from the sand, this vacation rental property features modern, well-appointed accommodations and easy access to nearby dining, shopping, and attractions. Whether you’re relaxing on the balcony or taking a dip in the pool, Island Paradise delivers a memorable beach vacation experience in the heart of Anna Maria Island.
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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.