Anna Maria Rentals with Fun & Games
Family Fun & Game Homes on Anna Maria Island...
From sunrise to sunset, Anna Maria Island is packed with awe inspiring sights the whole family will enjoy. The beach and a great pool are necessities, but wouldn't it be fantastic if your family had things to do at your vacation rental to make the time more enjoyable and memorable? We have an abundant selection of homes with extra activities like ping-pong, billiards, foosball, sit-down arcades, corn-hole, and even putting greens. Please use our filter search option to narrow down the perfect fun spot for your next Anna Maria vacation. Follow the Flip-Flops for a fun adventure.
63 properties available
Sand Castle by Anna Maria Island Accommodations 302 65th St, Holmes Beach, FL 34217 VRC19-000022 Welcome to Sand Castle by Anna Maria Island Accommodations, a bright five bedroom, three and a half bath vacation home in beautiful Holmes Beach. Perfect for families and groups, this island getaway offers the best of Anna Maria Island accommodations. A
Sweet and Salty by Anna Maria Island Accom modations 213 77th St, Holmes Beach, Florida 34217VRC20-000160Welcome to Sweet and Salty, a luxury vacation home in Holmes Beach featuring four bedrooms and four and a half bathrooms! This modern coastal retreat is perfect for families or groups looking for ultimate relaxation. Enjoy a dazzling private poo
Dolphin Pointe by Anna Maria Island Accommodations 711 Gladiolus St, Anna Maria, FL 34216 VR16-000318 Welcome to Dolphin Pointe, a beautifully renovated north end retreat that blends coastal charm with modern comfort. This three-bedroom, three and a half bath Anna Maria Island vacation home is just a two-minute walk to the white sand beaches, makin
Sweet Caroline by Exclusive Vacations 9306 Gulf Drive, Anna Maria, FL 34216 VR23-000009 Welcome to Sweet Caroline, part of our Exclusive Collection. This luxury four bedroom, four and a half bath Anna Maria Island vacation home just one small block from the Gulf beaches. This coastal retreat blends refined design, resort-style amenities, and a rel
Carefree Cay by Anna Maria Island Accommodations 217 Sycamore Avenue, Anna Maria, FL, 34216 VR16-000412 Welcome to Carefree Cay, a three-bedroom, two-and-a-half-bath vacation home in the north end of Anna Maria Island. Just a short two-block stroll from the soft white sands of Anna Maria Beach and the charming shops and restaurants along Pine Ave
Mojito Splash by AMI Locals 304 65th Street, Holmes Beach, FL 34217 VRC18-000068 Welcome to Mojito Splash, a stunning five-bedroom, three and a half bath waterfront retreat located just a short stroll from Holmes Beach’s white sandy beaches on Anna Maria Island! This beautifully designed home boasts a sparkling pool, dual waterfalls, a stone-edge
Hip Nautic by AMI Locals 870 N Shore Dr, Anna Maria, Florida VR22-000090 Welcome to Hip Nautic, a luxury four bedroom, four and a half bath beach retreat just steps from the beautiful bayside shores of Anna Maria Island. Perfectly situated near Pine Avenue’s shopping and dining, this modern, pet-friendly home offers upscale amenities including a pr
The Black Pearl by Exclusive Vacations 5612 Guava St, Holmes Beach, FL 34217 VRC23-000114 Experience luxury and coastal elegance at The Black Pearl, part of our Exclusive Collection. This stunning black and white designed beach home offers a private black-bottom infinity edge pool and panoramic Gulf views. Located within walking distance of the pri
The Sea Zoo by Anna Maria Island Accommodations 402 Bay Dr S, Bradenton Beach, FL 34217 Welcome to The Sea Zoo, your ideal bayfront escape on Anna Maria Island! This beautifully designed three-bedroom, three and a half bath home offers a perfect mix of relaxation and family fun, just steps from Bridge Street’s charming shops and waterfront dining.
Two Pina Coladas by Anna Maria Island Accommodations 123 46th St, Holmes Beach, FL 34217 VRC16-000094 Welcome to Two Pina Coladas by Anna Maria Island Accommodations, a luxurious six bedroom, four and a half bath home just one block from the Gulf beaches of Holmes Beach. Designed for large families and groups, this coastal gem combines resort style
Malibu Beach by AMI Locals 302 55th St, Holmes Beach, FL 34217 VRC18-000067 Welcome to Malibu Beach, an eight bedroom, seven bathroom luxury vacation home in Holmes Beach. Just a 5-minute walk to the white sands of Anna Maria Island, this multi-level retreat features a rooftop deck with panoramic Gulf and Bay views, a resort style pool with watersl
Sail Away by AMI Locals 241 Willow Avenue, Anna Maria, Florida 34216 VR19-000048 Welcome to Sail Away, a spectacular six bedroom, six and a half bath canal-front luxury home in the heart of Anna Maria Island. With a private dock, a resort style pool with a swim up bar, and a rooftop deck showcasing stunning island views, this vacation rental is des
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