Vacation Rentals with Private Pools on Anna Maria Island

Homes with Private Pools on Anna Maria Island...

The Beaches on Anna Maria Island are absolutely amazing. So is having a private heated pool right in the backyard of your vacation rental. Being able to cool off in a pool is one of the most requested items during an Anna Maria Island vacation rental search. It is definitely a must have item for your next vacation. Anna Maria Island Accommodations has a robust inventory of pool homes with a variety of distances to the beach and even some gulffront. Let us help you find your perfect pool home rental.


Properties Available 208 properties available
Highlights•Located on our Beautiful Bay Beaches•Steps from the Beach with Direct Beach Access•Resort Style Pool and Spa•Dog friendly with approval and additional fee•Water View Decks with Unobstructed Bay Views•Close Proximity to Bean Point and Gulf Beaches•Walking Distance to Pine Avenue Shopping and DiningExclusive Amenities: •6 Seat Club Car Cru
Hot HOT 78
Bay View Beauty
Anna Maria Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 16 guests
Rating 5 (56)
Highlights• 5-minute walk to the beach• Private Pool• Outdoor showerOur Place By The Sea761 Jacaranda Rd Anna Maria, FL 34216VR16-000359Welcome to Our Place By The Sea, an inviting vacation home with a private pool on the quiet north end of Anna Maria Island just a five-minute walk from secluded Bean Point Beach! This ground-level home has three be
Hot HOT 63
Our Place By The Sea
Anna Maria
Bedrooms 3 BR
Bathrooms 2 BA
Bathrooms 1 Half Bath
Guests 6 guests
Rating 5 (40)
Little Pink Houses by Anna Maria Island Accommodations718 Holly Rd Anna Maria, FL 34216VR18-000136Welcome to Little Pink Houses, an inviting vacation home with a private pool and hot tub just a quick stroll from secluded Bean Point Beach! This home has three bedrooms and three bathrooms, and one is above the garage, perfect for guests that love ext
Hot HOT 30
Little Pink Houses
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 4.9 (40)
Addison's Beach House by Anna Maria Island Accommodations 7203 Gulf Dr, South Unit Holmes Beach, FL 34217 VRC16-000188Welcome to Addison’s Beach House, your idyllic beach vacation getaway! Just a short 2-minute stroll from the breathtaking Gulf waters, this rental three-bedroom, two-bathroom home invites you to experience the warmth of soft sandy
Hot HOT 44
Addison's Beach House
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Rating 5 (30)
Sand Castle by Anna Maria Island Accommodations302 65th St Holmes Beach, FL 34217VRC19-000022Welcome to Sand Castle! Nestled in the heart of Holmes Beach, this stunning 5-bedroom, 3.5-bath home offers an idyllic escape for families or groups seeking a perfect beach getaway. Just two short blocks from the sandy shores, Sand Castle is ideally located
Hot HOT 43
Sand Castle
Holmes Beach
Bedrooms 5 BR
Bathrooms 3 BA
Bathrooms 1 Half Bath
Guests 10 guests
Rating 5 (33)
Highlights• Canalfront • Less than a 15-minute walk to the beach• Private heated pool• Game Room• Monthly MinimumDolphin Daze by Anna Maria Island Accommodations525 75th StHolmes Beach, FL 34217Welcome to Dolphin Daze, a canalfront vacation home with a private pool just an eleven-minute walk to Holmes Beach on the Gulf of Mexico! With three bedroom
Hot HOT 36
Dolphin Daze
Holmes Beach
Bedrooms 3 BR
Bathrooms 4 BA
Guests 6 guests
Highlights • 1.5 Blocks to the Beach! Access the Sand at the End of Willow Ave! Short Walk!• Private Heated Pool with Sun Shelf and Hot Tub • Large Covered Outdoor Entertainment Area with Bar• Entertainment Area with Pool Table & Outdoor Games• Multiple Balconies with Seating• Elevator• Extra Den with Wet Bar and Sleeper Sofa•
Hot HOT 52
SeaLuxe
Anna Maria
Bedrooms 4 BR
Bathrooms 5 BA
Guests 8 guests
Rating 5 (12)
Highlights• 2-minute walk to the beach• Rooftop deck• Putting green• Private pool with in-ground spa• Pet friendlyAlong for the Vibe by AMI Accommodations2403 Avenue C Bradenton Beach, FloridaWelcome to Along for the Vibe, a breathtaking three-story island home with seven bedrooms and seven and a half baths just steps from the sparkling, powdery wh
Hot HOT 29
Along for the Vibe
Bradenton Beach Pet Friendly
Bedrooms 7 BR
Bathrooms 7 BA
Bathrooms 1 Half Bath
Guests 17 guests
Rating 5 (16)
Coco Cottage by Anna Maria Island Accommodations113 Los Cedros Dr. Anna Maria, FloridaWelcome to Coco Cottage, the perfect family retreat on beautiful Anna Maria Island! Designed with families in mind, this canal front vacation rental is just a short, 4-minute stroll to the beach and a quick 2-minute walk to the shops and restaurants on Pine Avenue
Hot HOT 72
Coco Cottage
Anna Maria
Bedrooms 3 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (3)
Bay Breezes at Bayside Bungalow by AMI Locals 201 S Bay Blvd Bradenton Beach, FL 34217 VR18-000088 Welcome to Bay Breezes at Bayside Bungalow! This adorable Anna Maria Island vacation rental has two bedrooms and one bathroom, all decorated with a delightful coastal theme to give you that perfect beach getaway. With stunning Bay beaches directly ac
Hot HOT 22
Bay Breezes at Bayside Bungalow
Anna Maria Pet Friendly
Bedrooms 2 BR
Bathrooms 1 BA
Guests 6 guests
Rating 5 (63)
Highlights• Private Pool and In-ground Spa• Less than a 5-minute walk to the beach• BBQ grill• Ping pong table• Near Anna Maria Island trolley stopGarden Party by AMI Locals8104 Gulf Dr Holmes Beach, FloridaVRC20-000303Welcome to Garden Party - the perfect peaceful retreat! This three-bedroom, three-bathroom beach house features a stunning Zen-insp
Hot HOT 38
Garden Party
Holmes Beach Pet Friendly
Bedrooms 3 BR
Bathrooms 3 BA
Guests 6 guests
Rating 5 (4)
Called In Sic by Anna Maria Island Accommodations 813 Jacaranda Rd Anna Maria, FL 34216VR18-000103Welcome to Called in Sic, your luxurious four-bedroom, three-bathroom vacation rental located just a block from the stunning Bean Point on the serene north end of Anna Maria Island. Perfect for families, friends, or anyone looking to unwind, our beauti
Hot HOT 57
Called In Sic
Anna Maria
Bedrooms 4 BR
Bathrooms 3 BA
Guests 8 guests
Rating 5 (43)

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