Vacation rentals in Anna Maria

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Top-rated vacation rentals in Anna Maria

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Guest favorite

Condo in Holmes Beach

4.98 out of 5 average rating, 108 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

Sep 28 – Oct 5

G$38,381 GYD per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 12 reviews

Lamantin- 2 bed/2bath North End, beach 2 min walk

Welcome to the Lamantin, duplex on the North End of Anna Maria directly across from the beach with direct beach access 2 properties away. Relax at this updated 2 bed/2 bath tropical unit that has everything you could ask for. Rent one unit or both. Perfect for a group of extended family and friends. The master features a queen-size bed and ensuite bathroom. The second bedroom has a king-size bed. The updated kitchen is equipped with all the basics, including pots/pans to make a delicious meal.

Dec 6 – 13

G$98,547 GYD per night

Guest favorite

Home in Bradenton

5.0 out of 5 average rating, 10 reviews

The "Love shack" Bungalow

The "Love Shack" Bungalow is the Perfect Place for a Couples Getaway! It's also great for someone who is looking for a Nice Peaceful Relaxation Spot. Approx 1.5 Miles to the Beach. It's Very Secluded with a Privacy Fence Surrounding it. Beautifully Updated Inside with Granite Counters & Blue Colorful Epoxy Floors. Super-Fast Wi-Fi & 50" Smart TV with Free Movies & Apps. There's a Large Screened in Lanai with a Table, A Gas BBQ Grill, Washer & Dryer & a Big Fenced in Yard. We are Pet Friendly!

Nov 1 – 8

G$26,142 GYD per night

Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 46 reviews

Island Beach Paradise, Close to Everything, Bikes

This remodeled condo is in the ideal location for your Anna Maria Island getaway. Award winning restaurants, great shopping and a marina are right out your door. The world famous beach on the Gulf of Mexico is three blocks away. Bikes, beach cart, beach supplies are provided. The expansive park across the street has tennis, pickleball, basketball, skate park, playground, dog park, boat & kayak launch ramp. Relax on your deck and enjoy a coffee & the beach breeze through the palm trees.

Sep 18 – 25

G$33,568 GYD per night

Guest favorite

Home in Anna Maria

4.96 out of 5 average rating, 50 reviews

Steps to the Beach! Pool/spa! Golf Cart Included!!

Newly renovated elevated home on the prestigious north end of the island. There is over 2100 sq. ft of living area in addition to the expansive outdoor space including a large saltwater pool/spa, outdoor TV and seating area, outdoor dining area for 10, lawn games and numerous balconies both covered & uncovered. The house is across the street from the Bayfront Park and a 7 minute walk to the world renowned Bean Point. We have also included bikes & a 6 person golf cart for your stay.

Dec 10 – 17

G$222,248 GYD per night

Guest favorite

Home in Bradenton Beach

5.0 out of 5 average rating, 8 reviews

New! Sunset Beach View/Trolley/Bridge Street!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Aug 13 – 20

G$125,355 GYD per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 120 reviews

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Nov 29 – Dec 6

G$65,294 GYD per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 58 reviews

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean

This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedroom, 3 Bathroom home plus loft is professionally decorated throughout, with state-of-the art quartz counter tops, JennAir professional stainless-steel appliances, wide plank wood tile floors, bead board ceilings. All bathrooms have basket weave marble and quartz counters and there is a Whirlpool Washer & Dryer. The house has everything necessary for a perfect beach vacation.

Aug 17 – 24

G$143,766 GYD per night

Guest favorite

Condo in Bradenton Beach

4.87 out of 5 average rating, 61 reviews

Luxury, Fully Stocked, Next to Pool & Beach-202

Fully stocked condo, full kitchen, all the beach supplies needed. See my other listings here www.airbnb.c0m/p/ryant (replace the zero in .com with an o to get to link) Largest saltwater pool on island. Private beach access, plenty of space. Self-check-in, no contact with anyone. All units have their own parking. Unit has a full kitchen, grocery store is a mile down the road, plenty of open-air restaurants. Professional cleaning following CDC guidelines.

Aug 21 – 28

G$31,268 GYD per night

Superhost

Home in Anna Maria

4.93 out of 5 average rating, 40 reviews

Gulf Coast Paradise

Located at the North End of Anna Maria Island 3 blocks from the beach and 1 block from the bay. Brand new heated swimming pool. Three bedrooms, 2 baths with open living & dining floor plan. A large screened porch for ping pong and dining. Perfect for entertaining your friends and family. House is equipped with beach chairs, beach towels, boogie boards and toys for your day at the beach. Children supplies available upon request. Pak n Play, crib etc.

Apr 25 – May 2

G$143,896 GYD per night

Guest favorite

Guest suite in Bradenton

4.97 out of 5 average rating, 120 reviews

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

Jun 25 – Jul 2

G$15,886 GYD per night

Guest favorite

Cottage in Holmes Beach

4.98 out of 5 average rating, 50 reviews

Calypso-an Anna Maria Island Oasis+Private Pool

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers Granite countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa.

Oct 5 – 12

G$94,337 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Anna Maria vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Anna Maria's top sights

Bean Point Beach67 locals recommend

The Sandbar Restaurant168 locals recommend

Rod and Reel Pier111 locals recommend

The Waterfront Restaurant99 locals recommend

The Donut Experiment66 locals recommend

Two Scoops26 locals recommend

Other great vacation rentals in Anna Maria

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 29 reviews

ami skyview

Dec 14 – 21

G$209,713 GYD per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 11 reviews

Veselka - Canal front w private heated pool & dock

Oct 20 – 27

G$150,318 GYD per night

Guest favorite

Home in Anna Maria

5.0 out of 5 average rating, 20 reviews

Stunning new 4 bed/4.5 bath home with heated pool

Dec 13 – 20

G$233,319 GYD per night

Guest favorite

Home in Anna Maria

4.96 out of 5 average rating, 25 reviews

Anna Maria Chateau. Private Pool home

Nov 27 – Dec 4

G$168,192 GYD per night

Guest favorite

Place to stay in Bradenton

4.96 out of 5 average rating, 28 reviews

Seas The Day By The Bay

Nov 24 – Dec 1

G$24,286 GYD per night

Guest favorite

Condo in Bradenton Beach

5.0 out of 5 average rating, 16 reviews

AMI Perfect Experience

Nov 15 – 22

G$34,018 GYD per night

Guest favorite

Guest suite in Bradenton

4.98 out of 5 average rating, 61 reviews

Adorable Manatee Guest House

Oct 14 – 21

G$20,480 GYD per night

Guest favorite

Home in Holmes Beach

4.91 out of 5 average rating, 22 reviews

Backyard Bliss Anna Maria Island

Nov 16 – 23

G$89,996 GYD per night

Show all

Quick stats about vacation rentals in Anna Maria

Total rentals	850 properties
Rentals with a pool	700 properties have a pool
Pet-friendly rentals	290 properties allow pets
Family-friendly rentals	790 properties are a good fit for families
Total number of reviews	10K reviews
Nightly prices starting at	G$20,897 GYD before taxes and fees

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 290 vacation rentals for guests traveling with pets.
Do house rentals in Anna Maria have free parking?
Absolutely! We offer over 700 house rentals with free parking in Anna Maria. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Anna Maria

Top-rated vacation rentals in Anna Maria

Vacation rentals for every style

Houses

Apartments

Cottages

Popular amenities for Anna Maria vacation rentals

Stay near Anna Maria's top sights

Other great vacation rentals in Anna Maria

Home in Anna Maria

Home in Anna Maria

Home in Anna Maria

Home in Anna Maria

Place to stay in Bradenton

Condo in Bradenton Beach

Guest suite in Bradenton

Home in Holmes Beach

Quick stats about vacation rentals in Anna Maria

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How is the weather in Anna Maria?

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

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

What are the best places to stay in Anna Maria?

What are the best places to visit in Anna Maria?

What are some hiking trails in Anna Maria?

What are some family activities to do in Anna Maria?

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

Are there pet-friendly vacation rentals in Anna Maria?

Do house rentals in Anna Maria have free parking?

Destinations to explore