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 209 properties available
Highlights• 2-minute walk to the beach• Private Pool• Washer and dryer• Dog friendly with host approval and a $250 pet fee• Less than a 5-minute walk from Pine AveMermaid's Purse107 Palm AveAnna Maria, FL 34216VR16-000364 Welcome to Mermaid’s Purse, a perfectly located north-end vacation home with just two houses to Palmetto Beach and a quick walk
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Mermaid's Purse
Anna Maria
Bedrooms 2 BR
Bathrooms 2 BA
Guests 4 guests
Siena Sky by Anna Maria Island Accommodations 10109 Gulf Drive Anna Maria, FL 34216 Siena Sky, a new four-bedroom, four-and-a-half-bath home, beckons you to unwind, explore, and create cherished memories in style. Just a minute's walk from the beach, imagine starting your day on the rooftop deck with breathtaking water views, then strolling down t
Hot HOT 84
Siena Sky
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
Serendipity by Anna Maria Island Accommodations207 55th St Holmes Beach, FL 34217 VRC16-000107 Welcome to Serendipity, a gorgeous villa just one block from the white sands of Holmes Beach. This three-bedroom, two-bathroom single-level duplex sleeps up to six guests.Highlights • 3-minute walk from the Beach • Private Pool • Tiki Bar Relax and enjoy
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Serendipity
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Highlights• Private pool• Less than a 10-minute walk to the beach• Game room• BBQ grill• Outdoor showerOrange Crush by Anna Maria Island Accommodations312 61st St Unit BHolmes Beach, FL 34217Welcome to Orange Crush! This recently updated three-bedroom and two-bath home has been thoughtfully decorated and has a game room you'll love! It features arc
Hot HOT 59
Orange Crush
Holmes Beach
Bedrooms 3 BR
Bathrooms 2 BA
Guests 6 guests
Highlights•On Beach Block with Amazing Gulf Views•Steps from the Beach with Convenient Beach Access•Exciting Rooftop Putting Green•Rooftop Deck with Fire Pit and Panoramic Gulf Views•Resort Style Pool and Spa with Tanning Deck•Fun Games such as Cornhole and Pool Basketball•Fully Equipped Outdoor Kitchen with Living and Dining areas •Walking Distanc
Hot HOT 54
Palmetto Paradise
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Guests 8 guests
The James by AMI Locals 608 Rose St Anna Maria, FL 34216 The James is the ultimate beach getaway, featuring four bedrooms, four and a half baths, just moments from Anna Maria's renowned beaches. Enjoy incredible amenities, including a rooftop deck with breathtaking beach views, perfect for sunset moments. Plus, indulge in games like ping pong and
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The James
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
The Colony by Anna Maria Island Accommodations 227 S Harbor Dr, Holmes Beach, FLWelcome to The Colony, a custom-built vacation home with a breathtaking private backyard that features a spacious pool, hot tub, and a covered patio, great for entertaining and making memories with your friends and family! This home has four bedrooms and four and a half
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The Colony
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Love Me Blue by AMI Locals 792 Jacaranda Rd. Anna Maria, FL 34216Experience your vacation dreams at Love Me Blue! This stunning, brand-new luxury rental features 4 bedrooms and 4.5 bathrooms, making it the ideal choice for your family getaway on Anna Maria Island. A short walk leads you to the tranquil Bean Point beach, while just a mile away, you
Hot HOT 36
Love Me Blue
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests
Welcome to Just Beachy on beautiful Anna Maria Island!Have the trip of a lifetime at this beautifully appointed 6 bedroom 4.5 bathroom luxury beach house, just steps away from the sugary soft sandy beaches.This navy and white stunner is settled in the middle of Anna Maria Island, and is 400 feet away from the 65th Street beach access! The home was
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Just Beachy
Holmes Beach Pet Friendly
Bedrooms 6 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 12 guests
Pineapple Paradise by AMI Locals207 65th St Holmes Beach, FloridaVRC19-000039Come and visit Pineapple Paradise! This exceptional four-bedroom, six-and-a-half bath vacation home is just a few steps away from the beach. To provide our guests with an unforgettable experience, we have designed this house with a perfect backyard for entertaining and an
Hot HOT 44
Pineapple Paradise
Holmes Beach Pet Friendly
Bedrooms 4 BR
Bathrooms 6 BA
Bathrooms 1 Half Bath
Guests 8 guests
Highlights• 3 houses from Holmes Beach • Shared pool• Near free island trolley stop• Community washer and dryer• Near restaurants Palm Cay 6 by Anna Maria Island Accommodations 3000 Gulf Dr, Unit #6Holmes Beach, FL 34217VRC16-000127Welcome to Palm Cay 6, a ground-level corner unit that is less than a minute's walk to the powdery white sands of the
Hot HOT 24
Palm Cay 6
Holmes Beach
Bedrooms 1 BR
Bathrooms 1 BA
Guests 4 guests
The Curated Palm by Anna Maria Island Accommodations520 Kumquat Drive, Anna Maria, FLDiscover The Curated Palm, a stunning, spacious retreat perfect for group rentals, multi-family vacations, or extended stays with friends. This luxury 4-bedroom home offers an exceptional blend of comfort, style, and outdoor resort-style amenities. Located right on
Hot HOT 26
The Curated Palm
Anna Maria
Bedrooms 4 BR
Bathrooms 4 BA
Bathrooms 1 Half Bath
Guests 8 guests

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