Anna Maria Island & Holmes Beach Vacation Rentals - Privately Owned Professionally Managed®

Anna Maria Island luxury vacation rentals are our specialty and our customer rave about our personalized free service. We invite you to view the largest selection of Privately Owned and Professionally Managed Anna Maria Island vacation beach houses & condos. Exceptional vacation accommodations and on-call service during your stay.  If you are visiting during peak holiday weeks Call your local Emerald Kite agent today and request a FREE list of all suitable accommodations available for your dates. (Free complete area accommodation list can only be requested via phone).
Presenting the ultimate selection of vacation rentals on Anna Maria Island.

Our homes range from one bedroom beach condos to the ultimate beachfront homes with gulf views and private pools. Call your local agent today!

Marni - Emerald Kite Destination Agent

Call Our Local Agents 7 Days a Week from 9am - 10pm EST

USA: 941.900.4552

International: +1 941.500.4555

Our Most Popular 5+ Bedroom Anna Maria Island & Holmes Beach Rentals

Luxury Vacation Home 6 Bedrooms Anna Maria Island Sleeps 12

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 12
  • 6 Bedrooms
  • 3 Bathrooms

Anna Maria Vacation Home 7 Bedrooms 2 Kitchens! Top Rentals

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 5 Bathrooms

Almost Beachfront - Luxury Anna Maria Island Vacation Home

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 16
  • 7 Bedrooms
  • 5 Bathrooms

Our Most Popular 4 Bedroom Anna Maria Island & Holmes Beach Rentals

Anna Maria Island luxury Vacation Ocean Front Property

  • Platinum
  • Home/Villa
  • Pool
  • Max Occupancy: 8
  • 4 Bedrooms
  • 3 Bathrooms

Luxury 4 Bedroom - 2 Living Areas - Pool - North Anna Maria

  • Gold
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 4 Bedrooms
  • 4 Bathrooms

Anna Maria Island 4 Bedroom Vacation Rental Sleeps 12 Guests

  • Platinum
  • Home/Villa
  • Pool & Hot Tub
  • Max Occupancy: 12
  • 4 Bedrooms
  • 3 Bathrooms

Our Most Popular 3 Bedroom Anna Maria Island & Holmes Beach Rentals

Holmes Beach Luxury Condo Rental Communal Pool & Gulf Views

  • Platinum
  • Condo
  • Pool
  • Max Occupancy: 6
  • 3 Bedrooms
  • 3 Bathrooms

Anna Maria Three bedroom Condo Rentals Weekly Availability

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 6
  • 3 Bedrooms
  • 2 Bathrooms

Three Bedroom Luxury Condo - Upscale Interior - View of Gulf

  • Platinum
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 8
  • 3 Bedrooms
  • 3 Bathrooms

Our Most Popular 2 Bedroom Anna Maria Island & Holmes Beach Rentals

Anna Maria Island Beachfront Two Bedroom Beach Condo Rental

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

2 Bedroom Anna Maria Beach Condo Full Gulf Views Sleeps 4

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Condo with direct beachfront and superb Panoramic Gulf view

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 2 Bedrooms
  • 2 Bathrooms

Our Most Popular 1 Bedroom Anna Maria Island & Holmes Beach Rentals

Holmes Beach Vacation Condo Sleeps Two Guests.

  • Gold
  • Condo
  • Pool & Hot Tub
  • Max Occupancy: 1
  • 1 Bedroom
  • 2 Bathrooms

Direct Gulf Front One Bedroom Great Rates

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 4
  • 1 Bedroom
  • 1 Bathroom

One Bedroom Beach Rental on Anna Maria Island

  • Gold
  • Condo
  • Pool
  • Max Occupancy: 3
  • 1 Bedroom
  • 1 Bathroom
Marni - Emerald Kite Destination Agent

Call Our Local Agents 7 Days a Week from 9am - 10pm EST

USA: 941.900.4552

International: +1 941.500.4555

Anna Maria Island is a seven mile long South Florida barrier Island connected to longboat Key and with road bridge access points. The nearest major City is Sarasota which is a glorious bay side community with chic shopping, dining and world class entertainment.  At its widest point the island width is less than two miles making for easy access to both the Bay and Gulf beaches. The island attracts returning families year after year and the big draw is the unspoiled and easy access t its beaches. Activities are in abundance but this is not a touristy destination so sorry no fast food here! The local chamber of commerce provide an excellent service to visitors. 


Surrounded by the glistening Gulf of Mexico and the beautiful Bay Anna Maria Island offers vacation rental homes and condos on the beach or within easy walking distance to the beach. Its important to note that the Island only has around 700 Vacation homes with pools so booking your vacation rental early is important. Vacation  homes can be situated on or close to Bay or Gulf beaches with both offering a widely different beach experience. Those wanting a traditional South Florida beach experience tend to book rental homes and condos on the Gulf side and those bringing a boat and wanting easy access to the Bay and fishing like to book homes on Bay side.


 Larger homes with super sized pool are located in the Holmes beach area of the mid to North end of the island. Many of these North Anna Maria Island homes while not directly on the beach can access the beach without crossing a main road. Referred to as west of Gulf drive  these homes allow for easy Gulf beach access and no main roads  to cross which makes for an ideal location for those with young children. 


Anna Maria island is around a hour drive from Tampa International airport and Sarasota Bradenton airport is a few minuets away. There are no major hotels on Anna Maria so vacation homes and condos are the primary accommodation option. 


The South Gulf Coast of Mexico is possibly the most popular beach destination area in the United States. So what other beach destinations are close by? Longboat Key is connected by a bridge and leads you down to upscale Lido Key around 10 miles away. Anna Maria Island, Longboat and Lido Key are widely considered sister islands and many times visitors will stay at either beach location. Anna Maria Island does not have high rise buildings and is a family fun destination. Longboat and Lido key have a wide  selection of Miami style condos and beautiful luxury vacation homes with pools. 


 Now we have all heard of nearby Siesta Key with its quartz crystal sandy beaches. Siesta Key and sophisticated Sarasota is approximately 27 miles from Anna Maria Island and a wonderful alternate beach vacation location.


If Anna Maria Island is sold out for your dates here are the closest alternate South Gulf beach locations. 


Anna Maria to Longboat Key & Lido Key, is connected and only 10 miles apart

Anna Maria Island to Siesta Key -27 Miles  

Anna Maria Island to Casey Key-44 Miles

Anna Maria Island to Cleawater - 57 Miles

Anna Maria Island to Indian Shores 56 Miles

Anna Maria Island to Indian Rocks- 56 miles

Anna Maria Island to St Petersburg- 36 Miles

Anna Maria island to Venice- 44 Miles

Anna Maria Island to Boca Grande-76 miles

Anna Maria Island to Clear Water- 57 Miles

Anna Maria Island to- Cape Coral- 107 Miles

Anna Maria Island to St Petersburg-38 Miles

Anna Maria Island to Orlando- 140 Miles

Anna Maria Island to Naples-140 Miles

Anna Maria Island to Marco Island-153 Miles

Anna Maria Island to Captiva Island- 140 Miles

Anna Maria Island to the Key West- 396 Miles


Anna Maria Island Beaches include Manatee Beach which is situated on the West end of Manatee and has good parking, life guards and even a fun play ground for the children. Coquina Beach is on the Gulf side and has great picnic areas and grills. Bayfront Park is on the West end of the Island south of Bean Point. Bean Point beaches are on the North end of the Island and has some of the greatest sandy beaches with few visitors and a lovely quiet environment. 


Anna Maria is regarded as one of Florida’s most laid-back locales, but that doesn’t mean it lacks excitement! Pine Avenue offers a hub of great shopping, dining and bars and why not leave the car at home and enjoy the complimentary Anna Maria Island Trolley. There are plenty of activities for the whole family to enjoy. Check out our list of Anna Maria Island vacation activities. 

 

Golf
There are plenty of options for golfing near Anna Maria, and some of the best are in nearby Bradenton. For a quick round, visit the Pinebrook/Ironwood Golf Course. For a more challenging game, we recommend the Waterlefe Golf and River Club, which is also in Bradenton (and home to many PGA events).


For Kids and Teens
Anna marias Yolo Adventures offers exciting activities for the whole family, including parasailing, sunset cruises, and dolphin watching. You can also spend a day at the Clearwater Marine Aquarium, or rent bikes, boats, and kayaks from Just4Fun.

 

Spas

No vacation is complete without relaxation. For the ultimate spa experience, we highly recommend Acqua's Aveda on the Beach Spa, which offers hair design, massage, skin care, and men's services. Another great choice is the full-service Blue Door Spa and Salon, voted "Best Spa" by the Bradenton Herald for four years running.

When it comes to dining, Anna Maria Island is best known for its fresh, local seafood however, there are plenty of options to suit any taste. Emerald Kite Vacation Rentals guides its thousands of annual visitors to the best local dining establishments on the Island and recommends the following restaurants located on and close to Anna Maria Island.

 

The Beach Bistro
6600 Gulf Drive, Holmes Beach, Florida - this is beachfront dining at its finest. Enjoy steaks, seafood, signature cocktails, and decadent desserts at this acclaimed restaurant, which has been honored by ZAGAT, Wine Spectator, and The James Beard Foundation. Open for dinner only. By Far one of Emerald Kites top dining picks on Anna Maria Island.

 

Sharky's Seagrill 
2519 Gulf Drive North, Bradenton Beach, Florida.
Owned and operated by a European-trained chef, Sharky's offers seafood, steaks, pastas, and a full bar. The restaurant opens at 4 p.m. — just in time for happy hour! — and sandwiches and light bites are available at the bar until midnight.

 

The Sign of the Mermaid 
9707 Gulf Drive, Anna Maria, Florida
Nestled in a quaint, antique-filled home, The Sign of the Mermaid is a local favorite. The restaurant has a unique fusion menu, offering seafood favorites, vegetarian options, and Asian-inspired dishes. They serve breakfast, brunch, lunch, and dinner, and also have a full beer and wine list.

 

Mr. Bones
3007 Gulf Drive, Holmes Beach, Florida
Home to some of the most famous baby back ribs in the country, Mr. Bones is the place for BBQ on Anna Maria Island. Additionally, they also offer tasty vegetarian and vegan items, and are open daily for lunch and dinner.

 

Joe's Eats & Sweets

219 Gulf Drive South, Bradenton Beach, Florida
Craving something sweet? Joe's offers outrageous ice cream flavors, including key lime cheesecake, pineapple coconut, and white chocolate peppermint bark, just to name a few. They also have sorbet and sugar-free options, and are open until 10 p.m.

Anna Maria Island offers a great range of shopping options. From basic necessities to gifts and souvenirs and high end imported designer shopping.

 

Consider it Done


Consider it Done is a terrific concierge service utilized by  Anna maria Island vacationers. Services include grocery shopping, errands, yacht charter, babysitting and much much more. Nothing is to much trouble and this great company bends over backwards to ensure all your vacation needs are met and exceeded! Call your Emerald Kite Destination Agent to learn more about this amazing local service.

 

Groceries
Publix is Anna Maria Island's full-service grocery store. Located at 3900 East Bay Drive on Holmes Beach, it offers a bakery, deli, and fresh fruits and vegetables.

 

Specialty Boutiques and More
Stroll along Pine Avenue for boutiques galore. Pine Avenue also intersects with the Historic Anna Maria City Pier, where you can catch a fabulous glimpse of the bay. Additionally, Holmes Beach offers plenty of small gift shops, cafes, jewelry stores, and art galleries.

 

Outlet Malls
If you venture 30 minutes outside of Anna Maria Island, you'll find the Ellenton Outlet Mall, which features over 100 spectacular stores.Emerald Kite the leading supplier of high end vacation rentals brings thousands of visitors to Anna Maria Island from the U.S.A and International visitors just wanting to shop till they drop and fill their empty suitcases before they head back home. 

Anna Maria Island is situated between peninsular Florida and the Gulf of Mexico, just south of Tampa Bay. It's divided into three cities — Anna Maria occupies the north, Holmes Beach claims the center, and Bradenton takes up the southern portion of the island. Learn more about transportation on Anna Maria Island below:

 

Airports Close to Anna Maria Island
The Sarasota-Bradenton International Airport is located just 15 miles away, and the Tampa International Airport is 51 miles away. While the Sarasota Airport is closer, the Tampa Airport has a wider variety of air carriers.

 

Anna Maria island FreeTrolley
The Anna Maria Island Trolley is absolutely free, and offers an efficient way of exploring both Anna Maria Island and its posh sister barrier Island,nearby Longboat Key & St Armand's Circle. The Anna Maria Island trolley operates daily from 6 a.m. to 10:30 p.m. and many Emerald Kite guests forgo rental cars and pick up a driver or UBER at the airport and save, save, save! Following in the footsteps of world class resorts such as Vail Colorado & Positano Italy Anna Maria Island boasts this free transportation service resulting in guests returning year after year! The shuttle leaves every 20 minutes or so and many of Emerald Kite Anna Maria Island luxury vacation rental homes are situated within steps of the trolley stops. This incredible service is ideal for teenagers and those to young to drive rental cars. Young people love the freedom and independence to get around and parents simply take a well earned break from driving the young ones around!


Wherever you stay on Anna Maria Island the trolley stops are between 2 - 4 blocks apart with a few exceptions. Enjoy a shaded seated area at your stop and remember the trolley is air conditioned!  While the Anna Maria Island trolley (right now) is totally free the Longboat Key Trolley charges 75c. What a deal though. Pick up the trolley at Coquina beach and enjoy a breathtaking drive down picturesque Gulf of Mexico Drive, Longboats key main road that frames the Gulf of Mexico. Some of Florida's most amazing, ritzy beach homes are situated on Longboat key and you may spot the odd celebrity heading down to the beach.  Depart from the trolley pretty much anywhere along Longboat Key and enjoy the quiet, unspoiled and frankly underestimated world class beaches. No crowds here! Take the trolley further down Gulf of Mexico drive where you can visit St Armand's Circle, a fun and sophisticated  European style open plaza with an abundance of upscale boutiques, grocery stores, and fine and casual dining. Remember to check the trolley return times from St Armand's Circle as 11.00 pm is typically the last departure but holidays and weekends may vary.



Rental Cars
If you enjoy the convenience of a car — or you want to travel to other destinations, such as nearby Sarasota — you can find rental cars at nearby airports . Call your Emerald Kite agent today who will be delighted to assist with all your rental car needs while staying on lovely Anna Maria Island.