The Cast Villa sits in the heart of Anna Maria Island directly across from the famous Manatee County public beach W/life guard which features a gift/surf shop, restaurant, Tiki bar, live music and more. Beach is groomed daily and has lifeguards. Walk to Publix grocery store, CVS drug store and...

Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....

Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....

Recently renovated, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. Located in a quiet neighborhood with an easy 3-minute walk to the gorgeous white sand beaches of the Gulf of Mexico. You are less than a mile from historic Pine Avenue shops, restaurants, and the Anna...

Experience casual island luxury at this Holmes Beach getaway. Boasting plenty of room for the whole crew and even the family dog (for a small nightly fee), this getaway has it all. Stay in the heart of the island and enjoy a tropical shared pool with a 10-foot waterfall, a Tiki hut, and a communal...

This beach house is 'A Shore Thing' for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida room...

Adriel's Place in Anna Maria... A two bedroom located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, pavered terrace and pool overlooking sailboat water....

This 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the pristine white sandy beaches with easy access. It has a heated 16 by 34 foot pool shared with the identical rental house next door. This unit is fully furnished in tropical decor and has all the luxuries...

Escape with your loved ones to some of the best beaches in Florida! Anna Maria Island's sunshine, soft sands, and charming sights all await you at this dog-friendly cottage, with a shared pool to keep you entertained at home. Wake up and start your morning right with a mug of warm coffee and...

You’re sure to fall in love with island living when you book your Anna Maria Island vacation at the dog-friendly Coastal Sands. This professionally decorated home offers everything your family needs, including a private heated pool, and a location less than two blocks from the powder fine Gulf of...

Welcome to Buddy's Beach House. A beachy chic getaway just 2 blocks to the beach. Stroll to the beach with a beverage in one hand and your beach cart in the other. After soaking up the sun all day, walk to one of the many fine restaurants, only a few blocks away. Or hop on the free trolley, which...

Island Dream is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms / 2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the brand new (2018) luxurious heated pool and spa, gourmet...

This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 500 feet to the beach in a residential neighborhood, west of Gulf Drive. Decorated with simplicity, it is fully equipped with all the amenities which include: Full kitchen, washer/dryer, microwave, dishwasher, cable...

Welcome to this charming, dog-friendly Anna Maria Island house. With the private heated pool and hot tub, you will feel like you're miles away from your worries. There is a large, fenced-in backyard with lush landscaping, where you can soak up the warm island sun from a pool-side lounge chair....

Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the northern reaches of Holmes Beach,...

Enjoy a shared, heated pool with LED lighting and a full kitchen at this newly remodeled vacation rental located just a few blocks from shops, restaurants, bars, and more right in the heart of nearby Holmes Beach. Take a short walk over to miles of soft, sandy, Gulf Coast beaches just a couple...

This beautifully decorated 2 bedroom, 1 bath and 3 bedroom, 2 bath duplex is just a short half block from the white sand beaches of Anna Maria Island. The 2 bedroom unit sleeps 7 people and the 3 bedroom sleeps up to 10 people. Palm Haven is the perfect vacation spot for anyone! Amenities Include:...

DEALS DO NOT INCLUDE HOLIDAY WEEKS This brand new Stunning 3 bedroom 3.5 bathroom + den with bunk beds. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This...

Make this beautiful 3-bedroom, 2.5-bath vacation rental house your new home-away-from-home in Holmes Beach! Up to 6 travelers will have the luxury of swimming in the private pool or hot tub after kayaking in Palma Sola Bay. Take the provided wagon to the Gulf Beach a mere 2-minute walk away or...

Welcome to the SS Salamander, North unit at 121 50th Street in Holmes Beach. This recently updated two bedroom and one and one half bath unit is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's...

This brand new, dog-friendly (for a small nightly pet fee) Holmes Beach home is designed to inspire the ultimate vacation with the family. Sunset Glow's high-end details and trendy touches make for a truly relaxing vacation with a private heated pool - you may never want to leave! The Gulf of...

This home's Mediterranean design sets the scene for a luxurious island getaway! The backyard's heated pool is surrounded by palm trees, lounge chairs, and a propane grill. The whole family is welcome here, including dogs up to 25 pounds for a nightly fee. Located on a quiet cul de sac, one of...

This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a view over the water. Sit outside, fish off our dock, take out the kayaks, or just walk steps across the street to the beach! This is not your typical beach rental. It is our...

Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within walking distance to...

Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a Den where the kids can hang out with a TV and Queen Sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria...

Enjoy your own slice of island life with a stay at this charming, two-bedroom, waterfront condo. Located in a quiet, but vibrant neighborhood with plenty of local island flavor, there's room here for up to four guests along with the family dog for an additional nightly fee. Guests of this rental...

Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with...

A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside den which can easily serve as a third bedroom. It's exactly what you are looking for in a peaceful Anna Maria Island retreat. Located in a quiet, lakeside residential neighborhood, this unit...

Style, taste, and indulgence await you at this three-story Holmes Beach vacation home. From the moment you pull into the driveway, you’ll know a retreat filled with comfort and relaxation lies ahead. With a private pool, dog-friendly atmosphere (for a small nightly fee), and plenty of room for the...

Treat yourself to a fantastic, dog-friendly Anna Maria Island beach cottage with a perfect location and fun style. Fully updated in 2017 with stylish furnishings and décor, this home is only a few steps from the soft sands and warm waves of the Gulf of Mexico. You'll also enjoy perks like easy...

Relax in lush tropical island style in this Anna Maria Island condo! Island Serenity is beautifully decorated, and well equipped ffeaturing a shared pool, lush island views, and dog-friendly accommodations just a short walk from legendary white sandy beaches! Conveniently located in Holmes beach...

Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with...

When you reserve your stay at Pelican Landing AMI, you’ll experience the tropical vacation you’ve dreamed of! An ideal location and perfectly appointed amenities (dog-friendly as well!), you’ll instantly slip into the island life. Just a short walk to the beach, and a heated pool too. Florida...

Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3 bathrooms. Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200...

The Bman Beach Cottage located at 2812 Avenue B in Holmes Beach is a cute 2 bedroom 2 bath private home. This ground level home has two screened lanais one overlooking the pool and Jacuzzi. The kitchen has been newly updated as well as one of the bathrooms. This property has long distance and WiFi...

Spice up your next group get-together or family reunion with this fantastic new Anna Maria Island vacation rental! You'll enjoy gorgeous Gulf views, easy beach access, plus perks like a private pool and swim-up tiki bar! The soft sands and warm waves of the Gulf of Mexico are only a block away....

When you're feeling stressed out, there's nothing a little relaxation and vitamin D can't cure! Plan an escape to this lovely cottage on Anna Maria Island and enjoy island views, a private patio, access to a shared pool, and white sandy beaches nearby. Located in Holmes Beach close to the bridge...

Enjoy quite sunsets from your private screened balcony at this two bedroom two bathroom third floor condo with preserve views. The large kitchen with breakfast bar is well stocked wth everything you would need for preparing small meals to family dinners. The living room is furnished with a flat...

2 Bedroom 1 Bath Cottage On The Beach This cottage is located 'on the beach' 3007 Avenue F on beautiful Holmes beach. It is the upstairs unit (2 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space. This quaint cottage is hidden away on a dead end street, away from...

You'll fall in love with the relaxed lifestyle of Anna Maria Island at this two-bedroom Holmes Beach villa, a dog-friendly retreat with an ideal location for beach-goers and community amenities that include a heated swimming pool, a gazebo, and a picnic area. This quiet, ground-floor villa is...

The Siboney located at 3700 Gulf Drive in Holmes Beach, is an exquisite, executive level home with a private heated pool set amidst tropical, native landscaping. Its 2000 square feet of luxury! The beach is approximately one half block away with no major roads to cross. You can enjoy views of the...

Make yourself at home at this dog-friendly renovated house, nestled between the ninth hole of the Key Royale Golf Club and one of the island's canals. Off the living room you’ll find the backyard pool area, overlooking the water. This island home offers a heated pool and hot tub, gas grill, outdoor...

This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could...

Make your stay on Anna Maria Island unforgettable with this remodeled duplex with a private pool, as well as close proximity to the beach. This rental comprises an east and west section, each with its own kitchen, living area, and two bedrooms, and can accommodate up to 12 guests - perfect for...

Relaxation and sun-soaked fun are waiting for you at this charming Holmes Beach escape. Outfitted with a low-key, contemporary style perfect for a group of friends, you'll have access to a shared pool, a prime location, and parking for two vehicles. For a small nightly fee, you can bring your dog...

Come to Anna Maria Island and stay in this inviting condo with a shared pool, easy beach access, and walking distance to dining and shopping. You'll be able to park two cars in the designated spots and leave them there for the duration of your stay, thanks to the free, air-conditioned trolley. Your...

The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large...