Anna Maria Island Vacation Rentals
259 properties available
Buttonwood Cottage by AMI Locals 405 Pine Ave, Anna Maria, Florida 34216 Welcome to Buttonwood Cottage, a recently restored three bedroom, two bathrooms home full of Florida charm. Perfectly located on iconic Pine Avenue in Anna Maria and 10-minute walk to the Gulf. With a private heated pool, a pet-friendly policy, and easy access to island boutiq
Periwinkle Place by AMI Locals226 Periwinkle Plaza, Anna Maria, FL 34216Indulge in the ultimate luxury escape at Periwinkle Place, a stunning estate in the heart of Anna Maria! With six spacious bedrooms and six-and-a-half bathrooms, this meticulously designed home offers everything to elevate your island stay. Just a five-minute walk from the pris
Honeywood House by Anna Maria Island Accommodations 243 Willow Ave Anna Maria, Florida Relaxation and adventure await you at Honeywood House, a canal-front vacation home with a private dock and a beautiful backyard with a pool, spa, and plenty of space for entertaining friends and family. This three-bedroom, four-bath home is located on Bimini Bay,
The Palms 2 by Anna Maria Vacations Holmes Beach Vacation Condo VRC16-000099Welcome to The Palms 2, a beautifully updated second-level condo just one block from the stunning sands of Holmes Beach! Perfect for families or small groups, this refreshing Anna Maria Island retreat features two bedrooms and two bathrooms, offering comfort and convenience
Salty Seagull at Hunter’s Point by AMI Locals4321 Marina View Way, Cortez, FL 34215Enjoy an unforgettable island escape at Salty Seagull at Hunter’s Point, a brand-new canal-front vacation home just one mile from Anna Maria Island’s iconic beaches. This three bedroom, two and a half bath residence is located in an exclusive new sustainable communit
Sand Dollar by Anna Maria Island Accommodations Holmes Beach Private Pool & Hot Tub with Bay and Beach Access VR16-000117Welcome to Sand Dollar, a stunning vacation home featuring a sparkling pool and hot tub, just a short walk from Holmes Beach’s sugar-white sands! This three-bedroom, two-bath retreat offers a lush outdoor space with multiple
Tiny Tides by Anna Maria Island Accommodations520 Spring Ave Unit A, Anna Maria, FL 34216Welcome to Tiny Tides, a cozy and recently refreshed cottage-style getaway tucked in the heart of Anna Maria. This two-bedroom, one-bath home is perfect for couples or small families looking for a comfortable, budget-friendly place to stay while enjoying everyt
Called in Sic by Anna Maria Island Accommodations 813 Jacaranda Rd, Anna Maria, Florida 34216 VR18-000103 Welcome to Called in Sic, a stunning and newly renovated four bedroom, three bath luxury vacation home located just one block from the world renowned Bean Point Beach on the peaceful north end of Anna Maria Island! With a private heated pool an
Beach Haven by AMI Locals 5501 Holmes Blvd, Holmes Beach, Florida VRC18-000066 Welcome to Beach Haven, an eight bedroom, seven and a half bathroom luxury vacation home just a 5-minute stroll to the beautiful beaches of Anna Maria Island. This expansive, multi-level getaway is ideal for large family reunions or group vacations. With a private poo
Hurricane House by Anna Maria Island Accommodations 205 Spring Ave, Anna Maria, FL, 34216 VR16-000396 Welcome to Hurricane House, a charming and inviting vacation home just a three-minute walk to Anna Maria Beach and the iconic Pine Avenue. This ground-level retreat offers three bedrooms and two and a half baths, a private pool and a separate gues
Villa #8 AMI Lemon Fish by AMI Locals3602 6th Ave, Unit #2, Holmes Beach, FL 34217Welcome to Villa #8 AMI Lemon Fish, a cheerful two bedroom, two bath villa at the welcoming Islands West Resort! Just a two-minute walk from the sandy shores of Holmes Beach, this bright and beachy retreat is perfect for families, couples, or friends looking to experi
Coming in Hot by AMI Locals Anna Maria Island Luxury Home with Rooftop Deck and Pool VRC22-000171 Live the island dream at Coming in Hot, a stunning newly built four-bedroom, four-and-a-half-bath retreat located in Holmes Beach—just one minute from the sugar-white sands of Anna Maria Island. With a rooftop deck offering panoramic Gulf views, a res
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