
Anna Maria Island Vacation Rentals
Anna Maria Island offers some of the most desirable vacation rental homes on Florida’s Gulf Coast, known for its white-sand beaches, calm turquoise waters, and relaxed island lifestyle. Our collection of Anna Maria Island vacation rentals includes waterfront homes, luxury properties, and family-friendly beach houses designed to match every type of getaway.
Whether you're looking for a canal-front home with boating access, a private pool retreat, or a short walk to the beach, each property is carefully selected to provide comfort, convenience, and an authentic island experience. All homes are located in Anna Maria Island’s most popular area, the village of Anna Maria, close to Holmes Beach, and Bradenton Beach.
From romantic escapes to large family gatherings, our vacation rentals offer a wide range of amenities such as private swimming pools, putting greens, outdoor kitchens, tiki huts, backyard beaches, beautiful outdoor living spaces, and direct access to the island’s natural beauty.
For faster Mobile search click the clock icon to skip to your desired month
Sirenia Beach House
Sirenia Beach House vacation rental
-
Waterfront vacation rental in Anna Maria Island
-
Family vacation home with saltwater Pool & Spa
-
Family beach houses of Florida Gulf Coast
-
Anna Maria Island vacation rental with Dock
-
Guests voted one of the Best Places to Stay in Anna Maria
-
Located immediately next door to Sirenia Cove rental home
Features
Backyard Beach, Outdoor TV, Putting Green, Ping Pong Table, Tiki Huts, Hammock, Dock, Outdoor Shower, Pool, Spa, 2 Sets of Washer/Dryer/Refrigerator, Free WIFI, Free Fitness Center Access
4 Bedrooms, 3 Bathrooms
Sleeps up to 10
Starting at $2,599/wk
Over 2,200 sqft
Sirenia Cove
Sirenia Cove vacation rental
-
Waterfront vacation rental in Anna Maria Island
-
Family vacation home with saltwater Pool & Spa
-
Family beach houses of Florida Gulf Coast
-
Anna Maria Island vacation rental with Dock
-
Guests voted one of the Best Family Places to Stay in Anna Maria
-
Located immediately next door to Sirenia Beach House rental home
Features
Backyard Beach, Outdoor Bar TV, Ping Pong Table, Hammock, Dock, Outdoor Shower, Pool, Spa, Kayak Launch, 2 Sets of Washer/Dryer/Refrigerator, Free WIFI, Free Fitness Center Access
4 Bedrooms, 3 Bathrooms
Sleeps up to 12
Starting at $2,499/wk
Over 1,950 sqft
Sirenia By The Sea vacation rental
-
Waterfront vacation rental in Anna Maria Island
-
Family vacation home with saltwater Pool & Spa
-
Family beach houses of Florida Gulf Coast
-
Anna Maria Island house rentals for large groups
-
Anna Maria Island vacation rental with Dock
-
Guests voted one of the Best Large Group Places to Stay in Anna Maria
Features
Putting Green, Outdoor Kitchen, Cabana, Ping Pong Table, Hammock, Dock, Outdoor Shower, Large Pool & Hot Tub, 2 Living Rooms, 2 Sets of Washer/Dryer/Refrigerator, Free WIFI, Free Fitness Center Access
5 Bedrooms plus a Bunk Room, 5 Bathrooms
Sleeps up to 12
Starting at $2,800/wk
Over 3,880 sqft
Waterfront Vacation Rentals on Anna Maria Island
Our waterfront vacation rentals on Anna Maria Island offer a true island lifestyle, where the water is an everyday part of your stay. These homes are located along peaceful canals, bays, and coastal waterways, giving guests direct access to the beauty and tranquillity that make the island so special.
Many of our waterfront properties feature canal-front homes on Anna Maria Island with private docks, making them ideal for guests who enjoy boating, fishing, paddle boarding, or simply relaxing by the water. From sunrise coffee overlooking the canal to sunsets reflecting off the water, these homes are designed to connect you with the natural surroundings at every moment.
Whether you're planning a relaxing getaway or an active boating vacation, staying in one of our waterfront homes provides both comfort and convenience. You’ll enjoy easy access to the Gulf, nearby sandbars, and some of the most scenic waterways on Florida’s Gulf Coast, all from the privacy of your own vacation rental.
Anna Maria Island Waterfront rentals
Beach House Rentals & Gulf Access Homes
Our beach house rentals on Anna Maria Island are designed for guests who want to stay close to the shoreline and experience the Gulf Coast lifestyle at its best. These homes offer the perfect blend of comfort, convenience, and location, placing you just moments from the island’s white-sand beaches and turquoise waters.
For those seeking an even more immersive coastal experience, our beachfront vacation homes in Florida provide direct or easy Gulf access, allowing you to enjoy daily beach walks, swimming, shelling, and unforgettable sunsets just steps from your door. These properties are ideal for families, couples, and groups who want the beach to be a natural extension of their vacation.
Whether you're planning a relaxing seaside escape or an active beach-filled holiday, our carefully selected homes provide the ideal base for enjoying everything Anna Maria Island and Florida’s Gulf Coast have to offer.
Anna Maria Island Waterfront rentals
Family-Friendly Vacation Homes
Our family vacation rentals on Anna Maria Island are designed to bring people together in comfort, space, and style. Each home is thoughtfully selected to provide the amenities families need to relax and enjoy their time on the island, including spacious living areas, multiple bedrooms, outdoor gathering spaces, and convenient access to beaches, parks, and local attractions.
For larger gatherings, we also offer large group rentals on Anna Maria Island that make it easy for extended families and groups of friends to stay together under one roof. These homes provide the space and layout needed for shared meals, celebrations, and quality time, while still offering enough privacy for everyone to feel comfortable.
Whether you're planning a multi-generational family vacation, a reunion, or a getaway with friends, our homes are designed to create a seamless and enjoyable experience where everyone can relax and make lasting memories on Anna Maria Island.
Have a large group on a budget or with small kids? Sirenia Cove is your best bet with it's outdoor bar to line up the kids for lunch and its big outdoor pool.
Want a more relaxed, elevated beach house with indoor-outdoor living? Sirenia Beach House has a large screened-in lanai with a smaller pool for those who crave the island lifestyle.
Have a multi-generational or large group of friends? Sirenia By The Sea has 5 bedrooms, plus a bunk room as well as 2 living rooms to really stretch out.
Anna Maria Island Family Friendly rentals
Rentals with Pools, Docks & Outdoor Amenities
All of our Anna Maria Island rentals with pool are designed for guests who want to enjoy the island lifestyle both on and off the beach. Private pools provide a relaxing retreat after a day in the sun, offering a comfortable space to unwind, cool off, and spend time with family and friends in complete privacy.
For guests who love being on the water, we also offer boat dock vacation rentals on Anna Maria Island that make it easy to explore the surrounding canals, bays, and Gulf waters. These homes are especially popular with boaters, anglers, and anyone looking to enjoy direct access to the island’s scenic waterways right from their backyard.
In addition to pools and docks, many of our properties feature outdoor living spaces designed for island living, including covered patios, dining areas, grills, putting greens and lounge spaces, including some with backyard beaches! These amenities allow you to fully enjoy Florida’s warm weather and laid-back coastal atmosphere throughout your stay.
Anna Maria Island Rentals with Pools
Anna Maria Island Rentals with Hot Tubs or Spas
Anna Maria Island Rentals with Docks
Anna Maria Island Rentals with Backyard Beaches
Anna Maria Island Rentals with Putting Greens
Anna Maria Island Rentals with Outdoor Kitchens
Anna Maria Island Vacation Rentals - Last Minute Deals
Sorry Already Booked...Keep checking back for new deals.
Join our newsletter below to stay alerted to last-minute discounts!
Vacation Rental Restrictions
-
NO PARTIES!
-
NO SPORTS TEAMS
-
Dates and prices are deemed to be reliable but may not be entirely accurate. A personalized e-mail will be sent to you to confirm your reservation and pricing
-
Prices past December 31, 2027, are inaccurate; please inquire directly for pricing
-
Pricing is subject to change
-
Minimum Stay - 7 nights
-
Turnover Day - Saturdays
-
No Pets
-
Renter must be 25 years or older; proof of identity and age is required with the primary renter's government ID
-
All renters' names and ages must be collected under the Anna Maria vacation rental ordinance (for emergencies).
-
A credit card is required for each profile, regardless of payment method
-
Renters must adhere to the city of Anna Maria's noise and parking ordinances
Read our full terms and conditions HERE



