Holiday houses in Anna Maria

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Top-rated holiday rentals in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.
Home in Holmes Beach
5 out of 5 average rating, 51 reviews

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view

Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

Top Guest favourite
A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.
Home in Holmes Beach
4.95 out of 5 average rating, 113 reviews

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -We typically have shorter stays available, just ask! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

Top Guest favourite
A private heated pool is surrounded by lush tropical landscaping and tall palm trees. Two lounge chairs are positioned near the pool, and a shaded area is provided by a large umbrella. White fencing encloses the yard, enhancing privacy in the outdoor space.
Home in Anna Maria
4.97 out of 5 average rating, 31 reviews

Birdsong-Steps to Bean Point Beach Heated Pool!

Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

Top Guest favourite
Home in Holmes Beach
4.94 out of 5 average rating, 117 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on spa and the music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Guest favourite
The exterior of the white house features a welcoming front porch with two dark seating areas. A well-maintained pathway of gravel leads to the entrance, while lush greenery and decorative plants enhance the surroundings, and a festive wreath adorns the front door.
Home in Bradenton
4.97 out of 5 average rating, 166 reviews

Downtown Bradenton & close to Beaches, quiet area

Your family will be close to everything when you stay at this centrally-located private home with fenced in yard near downtown and beaches. Three bedrooms and 2 bathrooms await your next vacation to Florida's beaches. Located 1 mile to downtown - restaurants, shops, markets, Riverwalk, Theater, Bishop Museum and more. Only 4 miles to beaches. Stroll the neighborhood oak lined sidewalks and river. Front porch & private back fire pit & grill. Note - only 3 vehicles permitted.

Top Guest favourite
An aerial view captures the coastal neighborhood, showcasing a collection of charming homes with grey rooftops. The vibrant blue ocean and sandy beach are visible in the background, while lush palm trees surround the area, contributing to the serene island atmosphere.
Townhouse in Holmes Beach
4.99 out of 5 average rating, 149 reviews

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, snowbirds, reunions, and couples!

Top Guest favourite
A vibrant yellow cottage is depicted with a landscaped area featuring palm trees and a gravel yard. Colorful adirondack chairs in pastel shades of pink and blue offer seating options, creating a casual outdoor space. Nearby cottages are visible, enhancing the beachfront setting.
Guesthouse in Bradenton Beach
4.99 out of 5 average rating, 194 reviews

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Top Guest favourite
A serene outdoor area features a clear blue swimming pool, flanked by palm trees. Comfortable lounge chairs are positioned alongside the pool, and a shaded dining table is visible in the background. The white exterior of the building reflects a bright, inviting atmosphere.
Apartment in Holmes Beach
4.96 out of 5 average rating, 186 reviews

Cabin 2 at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, the free AMI trolley, and nightlife. You’ll love my place because of the location and the ambiance. It is nestled in the lush tropical landscape of Spinnakers Vacation Cottages. You will find Cabin 2 is a perfect spot for an island getaway. My place is good for couples, solo adventurers, families (with kids), and certain size breed and weight dogs. Spa maintains same temperature as pool.

Top Guest favourite
An aerial view captures a serene private pool encompassed by a stone patio, with several lounge chairs arranged nearby. Lush greenery and tropical plants border the scene, while a dark pond reflects the surrounding nature, enhancing a tranquil outdoor space.
Home in Bradenton
5 out of 5 average rating, 115 reviews

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Top Guest favourite
A bright dining room is shown with a handcrafted table accommodating six beneath stylish light fixtures. The open-concept living area features large windows, natural light, and relaxed seating. A refreshing pool area is surrounded by loungers and umbrellas, while a six-seater golf cart is parked nearby.
Townhouse in Holmes Beach
5 out of 5 average rating, 47 reviews

Dec Still Open! 2 Blocks to Beach + Heated Pool

Welcome to Salty Sunsets, hosted by Adored Luxe Getaways! Why you’ll love staying here: Salty Sunsets puts you just two blocks from the sand with a private screened porch, 6-seater golf cart, and community pool included. Inside, relax with a fully equipped kitchen, luxe bedding, and all the essentials for an easy island getaway. ☀ 5 minute walk to the beach ☀ 5 minute drive to Pine Ave. shopping & dining ☀ 15 minute drive to Bradenton

Top Guest favourite
A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.
Cottage in Anna Maria
4.96 out of 5 average rating, 259 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Top Guest favourite
A bright kitchen is showcased, featuring modern cabinetry and appliances. A small dining area with two wooden stools is positioned next to a white countertop. Natural light fills the space through a nearby door and window, creating an open atmosphere.
Home in Cove
4.99 out of 5 average rating, 115 reviews

Tranquility on the bay.

Tucked away from the hustle and bustle, my mobile home is located in a very unique neighborhood right on the bay with a little beach 2 min. down the road from my house, where you can sit and enjoy the views or fish. The homes are a combination of mobile homes like mine and houses with the most wonderful people of all walks of life. Very quiet, very safe and friendly. 5 min. to Bradenton beach and 10 min. to AMI.

Popular amenities for Anna Maria holiday rentals

When is the best time to visit Anna Maria?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$723 NZD$930 NZD$1,336 NZD$1,154 NZD$853 NZD$955 NZD$1,089 NZD$784 NZD$716 NZD$673 NZD$882 NZD$918 NZD
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Frequently Asked Questions

  • How is the weather in Anna Maria?

    Anna Maria experiences a tropical climate with warm, humid summers that generally reach 90°F (32°C) and mild winters hovering around 70°F (21°C). Rainfall is most common in the summer months, while winter remains relatively dry.

  • What are some of the best things to do in Anna Maria?

    Popular activities in Anna Maria include beachcombing, exploring the local dining scene, boating, fishing, and bird watching. For those interested in culture, visiting Island Gallery West, a co-op of local artists, is often recommended.

  • What is the best time of year to visit Anna Maria?

    The most popular time to visit Anna Maria is from February to May when the weather is warm and dry. During this time, the island hosts the Anna Maria Island Art League Springfest in March and the Food and Wine on Pine event in May, attracting many visitors.

  • What are the best places to stay in Anna Maria?

    Popular areas to stay in Anna Maria include the bustling Holmes Beach area, the serene Bean Point neighborhood, or the city center near Pine Avenue for its proximity to shops and restaurants. The Bradenton Beach area is also frequently suggested for its lively atmosphere and beachfront properties.

  • What are the best places to visit in Anna Maria?

    Frequently suggested places to visit include the historic Anna Maria City Pier, Bean Point Beach for its tranquil atmosphere, and the island town of Bradenton Beach. The Anna Maria Island Historical Museum is popular for those interested in local history.

  • What are some hiking trails in Anna Maria?

    Though Anna Maria is known more for its beaches, lovers of the outdoors can take a leisurely walk along the Coquina Baywalk at Leffis Key, a trail with abundant wildlife. The Robinson Preserve in nearby Bradenton, a 15-minute drive away, also has numerous walking and biking trails.

  • What are some family activities to do in Anna Maria?

    Families often enjoy exploring the Anna Maria Island Historical Society to learn about the area's past, embarking on dolphin watching tours, or spending a day at Bayfront Park, a beachfront area with a playground and picnic spots. Another frequently suggested activity is visiting the Island Gallery West, a local artist co-op.

  • What are some of the best day trip ideas in Anna Maria?

    A day trip to the nearby city of Bradenton, just 10 miles (16 km) away, is often recommended for its rich history and vibrant arts scene. Alternatively, you could explore the De Soto National Memorial, about 7 miles (11 km) away, or venture further to Tampa, 60 miles (96 km) away, known for its exciting theme parks.

  • Are there pet-friendly vacation rentals in Anna Maria?

    Four-legged friends are welcome in Anna Maria. Choose from more than 180 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Anna Maria?

    Yes! Work meets play with ease at over 210 vacation rentals in Anna Maria featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Anna Maria vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 410 vacation homes with pools in Anna Maria, available on Airbnb. Make a splash and soak up the sun in style!

  • Do condo rentals in Anna Maria have air conditioning?

    Absolutely! We offer over 30 condo rentals with air conditioning in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Anna Maria?

    Experience the best of Anna Maria with our apartment rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Anna Maria have wifi?

    Absolutely! We offer over 30 condo rentals with wifi in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Anna Maria have a bbq area?

    Absolutely! We offer over 10 apartment rentals with a bbq area in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Anna Maria?

    Anna Maria has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Anna Maria have a gym?

    Absolutely! We offer over 80 house rentals with a gym in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Anna Maria?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Anna Maria

  • Total holiday rentals

    Explore 490 holiday rentals in Anna Maria

  • Nightly prices starting at

    Anna Maria holiday rentals start at $160 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    450 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 180 rentals that welcome pets

  • Holiday rentals with a pool

    410 properties feature pools

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

  • Wi-Fi availability

    490 of Anna Maria holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Anna Maria rentals

  • 4.8 Average rating

    Anna Maria stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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