Anna Maria Vacation Rentals
View Top Destination Searches
Rental Type
Bedrooms
Bathroom
Pets
Amenities
Search Radius
Surrounding Areas

Click the pins to select or deselect an area.

Loading...
Proximity
Condo Complex
Apply Filter ×

Anna Maria Vacation Rentals

  • Guaranteed Bookings with 100% Protection

  • Easy Changes & Cancellation

  • 24/7 Emergency Support

Todd B. VaycayHero Guest

"Glad I discovered VaycayHero. Super easy to use with lots of inventory. Will be using more in the future."

Sort By
Recommended
Rating

1363 rentals are available

  • Willow Cottage is a lovely ground level bungalow in Anna Maria just waiting to give you that tropical vacation you dream of and deserve! This private rental home is stylishly decorated with touches of both new and old Florida. From the whimsical coastal print comforters to cool tile floors under your feet, each day will let you feel both away from it all and right at home in paradise.

    Up to eight guests can fit comfortably throughout the three bedrooms ,Queen sleeper sofa and two bathrooms at 108 Willow. (3) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins & Queen sleeper sofa

    A very private master bedroom with queen sized mattress is attached but separated from the rest of the home and it is all nestled in a charming cul-de-sac to let you feel even more away from it all. But the free wireless internet connection does provide a link to everyone back home. Just in case you get to wondering how it’s going back in real life.

    The bungalow sits just three properties away from a wooden walkway leading you to the sugary, pulverized quartz sand beaches you can only find on the gulf coast of Florida. A custom heated pool was just completed so that you can enjoy the Gulf of Mexico by day and a tropical backyard paradise at night! Fire up the propane grill around sunset and dining alfresco will take on a whole new meaning. Food just plain tastes better with that island air opening up your senses and a vivid sunset bursting in the sky. Sun loungers and an outdoor dining table with chairs will keep everyone comfortable while they chow down and get in some long overdue quality time together.

    Whether you stay a week or a month you can never run out of things to do and see on this beautiful barrier island - walk just a few blocks north to the famous Ginny and Jane E's for pastry and coffee each morning. For the nighttime, just across Gulf Drive you’ll find Slim’s which has pool tables, an island famous lobster mac and cheese, and live music! And if the days of sunshine and sand leave you too tired to walk, hop onto the free Island Trolley. Anyone who’s ever been on our seven miles of paradise knows the trolley is a charming and comfortable way to get anywhere you need to go.

    Amenities include Wireless Internet Access, 3 driveway parking, Washer/Dryer, Heated pool, Premium Linens, Pet friendly under 25 lbs.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: 2 Twins | Living Room: Queen Sleeper Sofa.

    Square Footage: 1216 Square Feet.

    Please don't change 108 Willow too much - we love it as is! (We do enjoy the improvements the new owners have made, however, and their extra touches such as beach towels, heated pool, quiet HVAC, games, etc.)

    Anna Maria
  • Bikini Bottom on Periwinkle is just a short walk -- only nine houses -- to the beautiful, pristine beaches we’re famous for! This vacation home is tucked away in a quiet neighborhood on the cusp of Holmes Beach and Anna Maria City so you’ll never be far from any of the favorite island activities. Everything from shopping on Pine Ave to paddle boarding is close by and easily reachable on foot or the free Island Trolley. However you spend the day, Bikini Bottom is a stylish and serene spot to come home to.

    From the moment you unpack, everyone will be on island time. (3) Bedroom, (2) Bath, accommodates up to (8) people: 2 Kings, 4 Twins, 1 Queen Sleeper Sofa. The sunshine and comfy furniture welcomes you to sit back and relax -- you're on vacation and life is going to moving at a more leisurely pace for your stay on Anna Maria Island.

    Two of the three bedrooms offer king size beds and all of them are equipped with a flat screen. There are double doors in the second bedroom which also has a door going out to the pool area. A third bedroom offers a set of twin beds with trundle and plenty of games so the kids can have a space all to themselves. Off the dining area is a charming Florida Room that leads directly out to the pool deck. It's a great space to curl up with a book when you don't feel like watching the TV and have a lot of space all to yourself. Of course, there’s also great lighting out in the backyard.

    The pool area is sunny and spacious - you won't want to leave it! And the pool is actually a salt water model which proves gentler on skin and bathing suits. There is the wading area at one end as well as a spa to sit and relax in while sipping on tropical cocktails. There is ample outdoor seating, a deck and shuffleboard court all surrounded by privacy fencing and lush Florida landscaping. Cook out on the charcoal grill under the world famous Anna Maria Island sunsets on a nightly basis.

    The vacation rental is also equipped with wireless internet and printer for use just in case you have to work during your visit. Enjoy the 52" flat screen TV with a family movie night.Bonus features include a baby monitor, play pen, walkie talkies and a queen size inflatable mattress.

    All these wonderful details will make your vacation to Bikini Bottom in Holmes Beach just perfect. Book with Island Real Estate today and you’ll be taking your first steps towards paradise. Reserve your holiday now!

    Amenities include wireless internet access, dishwasher, full size washer/dryer, open patio, deck, 3 parking spaces, heated pool & spa.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: 2 Twins with Trundle | Living Room: Queen Sleeper Sofa.

    Square Footage: 2340 Square Feet.

    Best time ever at Bikini Bottom! The house and pool areas were wonderful. Anna Maria beach is lovely! Never used our rental car, took the trolley every where, even grocery store! Looking forward to next year. Thank you owners:)

    Anna Maria
  • Adorable four bedroom and two bath beach cottage rental so close to the beach you can smell the salt air. The sugar sand beach is only steps away at the end of the street. This "Old Florida" beach house is tucked away in a quiet neighborhood of Anna Maria City. This property is just a few minutes walk to the beach!

    White picket fences, Savannah shutters and lush Florida landscaping give this property a "down home" Anna Maria Island feel. The interior is comfortably furnished to handle large groups. The beach home was extremely progressive in it's day as the kitchen, dining area, and living areas are all open to encourage reconnecting with friends and family in the Great Room.

    The Great Room includes a large flat screen TV with DVD player that can be seen from the kitchen or while sitting in most spots of the dining room table. There is an additional 5 seats at the bar counter in the kitchen. Between the dining table and bar counter, 11 can be comfortably seated and there is plenty of room for more inside or out.

    This unique beach rental boasts a SECOND living area or bonus room that has been set up primarily for children in the group although the set up is not absolute. The second living area has sectionals as well as a flat screen television equipped with a DVD player, fooseball table and a PLAYSTATION II to ensure everyone has fun on vacation.

    Bring along your favorite PS II games and gaming gear. Just off the second living area is the extra large patio to the pool, outdoor seating, and barbecue. The new pool is heated with a beautiful waterfall, lush tropical landscaping, seating for 10, and recliners for sunbathing.

    The easy access from the second living area makes outdoor entertaining perfect for children and friends. Most of the home is equipped with terrazzo floors so the home is truly BEACH Friendly for all ages. Lastly, the master bedroom includes a flat screen television. So much better than hotel living. Once you holiday here you will want to return to Anna Maria Island again and again!

    Amenities include wireless internet access, dishwasher, washer/dryer, open porch, car garage, heated pool 27 ft x 6 ft, 5 ft deep.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: 2 Twins | Bedroom 4: Bunk | Living Room: 2 Queen Sleeper Sofas.

    Square Footage: 1624 Square Feet.

    Please Note: the weight limit for dogs is 25 pounds - strictly enforced

    We really enjoyed our stay!

    Anna Maria
  • Sundrenched and colorful, Dolphin Watch is as beautiful inside as the landscape surrounding it. Which is something really special when you're directly on the flour soft, Gulf of Mexico beaches. Take in the vista of slowly rolling sand dunes and deep turquoise waters from all throughout the property.

    Color is key at Dolphin Watch with décor that somehow can be invigorating and tranquil all at once. Serene sky blue sits in the background of a fluffy, white queen bed while rich, exotic orange adorns the walls of a guest room with two twins. Coral walls in the bathroom will having you perking up in the morning, ready to start the daily grooming in front of a blue glass basin sink. The extra-large stand up glass shower gives plenty of room to wash your cares away.

    Sink into luscious, coffee colored color couches in the living room and soak up a different kind of view on the large, Plasma flat screen TV. DVR is also available through the cable provider. Catch up on the last season of your favorite TV show or with everyone back home on your laptop. Free wireless internet is set up throughout the property.

    When you’re ready to get out and explore the rest of Anna Maria Island, hop onto the free air conditioned trolley and ride it down through Holmes and Bradenton Beaches. You will be within walking distance of the famous Sandbar Restaurant, but get your order to go so you can enjoy one of the best tables on the island right outside your back door. Watch the sun melt away like the butter over your lobster on a private wooden patio.

    Anna Maria City also offers several historical points of interest. Check out the vintage City Jail or Island Museum off Pine Ave. The Rod N Reel Pier gives you the opportunity for fresh local seafood, whether you want to buy it by the pound or catch it yourself.

    Over the course of a week, you’ll spot parasails, boats, and porpoises out your windows, with a million dollar view of every sunset. Anna Maria Island is notorious for a crimson, purple, and golden light show at the end of every day and you won’t find a better vantage point than this. Yellow walls and open windows frame the scene from your living room, kitchen, and dining room.

    The open layout brings sunshine and scenery to everyone no matter where you’ve made yourself comfortable. Start planning your holiday to this gulf front vacation rental in Anna Maria City. After a week at Dolphin Watch, you’ll have a smile as wide as our porpoise friends.

    Amenities include Wireless Internet Access, 2 Driveway parking, Washer/Dryer, Open Patio, Premium Linens.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Set of Twins | Living Room: Queen Sleeper Sofa.

    Square Footage: 868 Square Feet.

    We have rented through your office 5 times and have always enjoyed our stays!

    Anna Maria
  • Welcome to 509 South Bay Blvd right across from the bayside beach and a short stroll to Pine Ave shopping and dining. This tastefully updated elevated home is ideal for a family weeks' vacation to spending the winter here on beautiful Anna Maria Island. You will have plenty of room for the whole family with this 5 bedroom 3 bath home. Sit by the tropical court yard garden and spend your time in the heated pool. Pet friendly - under 50 lbs.

    Watch the sunrise overlooking Tampa Bay and views of the Sunshine Bridge from one of the many well-appointed covered decks. Bay beach access is 50 feet away! Plenty of parking in the two car garage. You will make this vacation home your special re-treat and you will want to come back year after year.

    Amenities include wireless internet access, 2 car garage & driveway, washer/dryer, heated pool, dishwasher.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: Queen | Bedroom 4: 2 Twins | Bedroom 5: 2 Doubles.

    Square Footage: 3000 Square Feet.

    All Decked Out was fantastic. There was everything you could possibly need in the kitchen and more. The location was perfect. Short walk to town with shops, restaurants and piers. Across the street from the Bay Beach and about 6 blocks from Gulf Beach. Beautiful sunsets. Lovely heated pool. Three newly remodeled bathrooms with 3 walk-in showers, 1 tub. Ample towels. Furnished decks everywhere. TV's in every room and WiFi. It is perfect and we had a wonderful time. Be aware there are a lot of steps.

    Anna Maria
  • Welcome to 721 Holly Road located on the northern end of beautiful Anna Maria Island.

    This lovely single family elevated three bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool & spa overlooking the lagoon mangrove canal with private outdoor shower.

    Boats under 25' can pull right up to the dock located in the back of the yard. You will think you are on your own private island oasis. A wonderful area to walk in the evening and a short stroll to one of the sugar sand beaches. Come for the sun/fun and stay for the sunsets. Pet friendly - under 50 lbs.

    Amenities include wireless internet, driveway parking, 2 car garage, washer/dryer, screened lanai, boat access, heated pool with spa, premium linens, dishwasher.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: 2 Twins.

    Square Footage: 2000 Square Feet.

    We had a wonderful time on AMI. The house was great!! Definitely will rent through Island Real Estate again.

    Anna Maria
  • Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island, you’ll find a vacation rental home appropriate to the name - "Pretty Palms" on Periwinkle Plaza. This three bedroom, two bathroom cottage is cozy, colorful and full of natural light letting you feel refreshed enough to get out and enjoy more of our local, natural beauty.

    Get yourself on island time right away and take in the front yard’s thriving landscape. Any post flight crankiness will melt away at the sight of palm trees swaying in a coastal breeze. Just wait for the end of the day when sunset becomes part of the scene. We think you’re really enjoy life in a postcard.

    Once inside, you’ll see the open layout spreads out into a living room, kitchen, dining and sun rooms so everyone can enjoy their time together with plenty of space. Furnishings and decors are not old or new but timeless Florida style.

    Refreshing, exuberant yellows will put you in that sunnier island frame of mind. Soothing greens and blues evocative of sea glass in the bedrooms will help you unwind at the end of a long beach day. The master is situated on one side of the house and the others are separate which creates a split plan with ample privacy. Additional features include a queen bed, walk-in closet and attached bath with double walk-in shower.

    The vacation rental home is equipped with wireless internet and a desk area just off the kitchen should you have to work during your stay. The fully equipped kitchen is a perfect place to whip up lunch and snacks before the beach. Marinade meats and prepare kabobs for the propane grill out back. Everyone can sit at the breakfast bar and start dinner conversation early while preparing meals. But don’t forget, some delicious restaurants are just a short stroll or free
    trolley ride away!

    One attraction you won’t have to go far to get to is the tropical oasis waiting for you right out back. The heated pool area is one of this vacation rental home’s prime features. Between palm trees, lounge chairs, and a shallow wading area
    for tanning, you’ll be able to feel even further away from the stresses back home. But rest assured there are worse ways to spend an afternoon in paradise.

    Amenities include wireless internet access, 3 spaces parking, washer/dryer, open lanai, heated pool, premium linens.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Queen | Bedroom 3: 2 Twins.

    Square Footage: 1860 Square Feet.

    This house is beautiful and at a great location. This is our second year in a row staying here! Hopefully we can make it three in a row next year!

    Anna Maria
  • Welcome to "Holly Hideaway" located on the northern end of beautiful Anna Maria Island. This lovely two bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool located in the back of the yard.

    You will think you are on your own private island oasis. A wonderful area to walk in the evening and a short stroll to one of the sugar sand beaches. Come for the Sun/Fun and stay for the sunsets. Small dogs are welcome!

    Amenities include wireless internet access, under house parking, fulll size washer/dryer, dishwasher, screened lanai, heated pool, pet friendly (dogs under 25lbs), premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Living Room: Double Sleeper Sofa.

    Square Footage: 1130 Square Feet.

    This is a beautiful, well furnished and well kept home.

    Anna Maria
  • There is getting away from it all and there’s completely removing yourself from reality. Experience a near ethereal level of luxury by spending a week at the vacation home so wisely and whimsically dubbed Rest A Shore. It wouldn’t really be giving this vacation home justice to just describe the amenities of this wonderful vacation home directly on Tampa Bay...it’s a fully immersive experience. So let’s walk you through it:

    The drive to 838 S Bay Blvd is both a feast for the eyes and long enough to make you think you must have somehow missed it. But we promise there is still nothing but blue skies; Rest A Shore offers the utmost privacy. You’ll pass indulgent homes in the style of old and new Florida architectures and when you see yachts and sailboats docked at the marina, you’ll know you’re almost there.

    Pulling up into the driveway, tucked away behind a cascade of saw palms and silver buttonwood tree, is the home plucked straight from vacation dreams you never realized you always had. The cars can stay parked in the driveway or protected from Florida sunshine and rain in a separate two car garage. With suitcases in hand, you’ll walk up to the front door, a balmy bay breeze swaying the palms trees and a rope hammock. You don’t exactly have a front yard…more like your own private shady grove spreading out and around your new home away from home in paradise. 

    You can catch a glimpse of all the wide open space and sunshine through the glass of the front door but once inside, the pure decadence of this house comes over you. This effervescent luxury rental is a balance of modern comfort and casual beach living, and it all sits against an endless backdrop of the bay and pool deck.

    The heated* pool sits shimmering like a crown jewel in the pool deck. You think of how golden tan you’ll be after a few days lounging in the flamingo pink chairs. Let the kids play Marco Polo all day and they’ll be tuckered out early. Giving grownups time to enjoy a soak in the hot tub.

    During your stay you’ll notice how Florida waters change with the time of day. With the Sunshine Skyway Bridge sitting on the horizon, the bay water shimmers in silver and gray during the slow creep of morning. By the time the sky has exploded into sunset, gold coins seem to glisten and bob in the water under a heavy, melting sun. You’ll never see the same vista twice and it all sits living and breathing right outside, visible from most rooms of the house.

    Take in the best vantage point by climbing a glamorous spiral staircase to the master bedroom.  A king bed sits in this romantic little nook with wide windows giving an even higher look across Anna Maria Island’s natural beauty. Let yourself wake up slowly out on the deck. Sunshine pouring through sliding glass doors is a lovely alternate to alarm clocks. It even has a FoosBall table!

    This is a house that doesn’t give you a mere taste of island life; this home celebrates it. And it can be the place where some of your most treasured travel memories happen. Spend a truly spectacular honeymoon away from everything except the one you love. You can finally get everyone in the family together at Rest Ashore; eight people can sleep comfortably in this vacation home and it’s impossible to imagine feeling cramped. Family vacation and special events are the time when the handed-down-for-generations recipes come out and this vacation home is more than ready to accommodate.

    The appliances are all updated and in the case of the refrigerator, extra-large with room for all your holiday eats and treats. The warm and welcoming kitchen island will quickly become a favorite gathering spot for company and conversation. The marine blue dining table sparks dinner conversation and with full bellies you can watch all your favorite movies on a wall mounted flat screen. Or simply load up the dishwasher and stay around the table for a good old fashioned board game night. It is a vacation rental classic activity after all.

    During cooler months, open the bay front doors a crack and spark up the fireplace. Some music, some appetizers and someone to cuddle with on the cushy, tropical colored couches will put you in a state of relaxed bliss some people actually believe can only be found in high rise hotels. We love our local spas like Acquea Aveda and Salon Salon, but you can have your own day of beauty treatments in any one of the bathrooms. Give yourself a pedicure perched on the edge of a sunken tub where you just took your first bubble bath in years. Or let all that stress from back home wash away among the chic glass tile work of a tucked away shower in the guest bedroom.

    Any indulgence you could want in a vacation home can be found at Rest Ashore. Start planning your escape to this luxury rental on the north end of Anna Maria and book with Island Real Estate today.

    Amenities include wireless internet access, 2 car garage, driveway, 2 sets washer/dryer, heated pool & spa, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: 2 Twins | Bedroom 4: 2 Twins.

    Square Footage: 3000 Square Feet.

    Private and quiet-had a great week!

    Anna Maria
  • Paradise Pointe located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two bathroom vacation rental single family home is located on a lagoon canal and has a private heated pool & spa. Also, it is about 2 blocks to the Bean Pt and the best sugar sand beaches you will find anywhere on the West Coast of Florida. Spend the day on the beach and then go back for an afternoon nap but make sure you go back to watch a magical sunset on the Gulf of Mexico.

    This holiday rental comes with everything from a gas grill to garage parking. Inside you will find this beautifully done and furnished home to make your stay one that you will want to come back year after year. Sounds like a great vacation so book your next holiday stay at Paradise Pointe located at 411 Poinsettia.

    Amenities include wireless internet access, car garage, driveway parking, washer/dryer, limited boat access, heated pool & spa, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: 2 Twins | Living Room: Queen Sleeper Sofa.

    Square Footage: 1750 Square Feet.

    We really enjoyed the dock on the canal and the manatee in the canal and the landscape around the pool!

    Anna Maria
  • Welcome to "My Sister's Beach House" located at 520 Bayview Place on beautiful Anna Maria Island, Florida. This luxurious home has just been all updated and welcomes the vacationers who want to make their time on our beautiful island a wonderful experience. This luxury vacation rental is located on the highly desirable North end of Anna Maria Island, on a quiet cul-de-sac street. This house features a large dock with water, power located right on the canal leading to Bimini Bay and the Gulf. The boater in you will be able to get out to open water in minutes for some of the best fishing on the West Coast of Florida. Water and power are available dockside. Bring back the day's catch and fire up the full sized propane grill for dining alfresco. For the land lovers, relax canal side in the large heated pool and spa.

    Outside multiple lounge areas offer options to welcome chats over cocktails or quiet reading time alone, with breathtaking sunsets. The lush landscaping, including native mangroves,will make you feel that you are cocooned in your own private oasis. This 5 bedroom 4 bath multi-level home offers plenty of room for the entire family. There is plenty of parking including four garage spaces and two driveways for those boat trailers. The house has an elevator running to all 3 levels. There are two king size master bedroom suites, each with a large private bathroom. The other bedrooms have two king beds and two XL Twin beds.

    All bedrooms offer large flat screen TVs as well as iPod docking stations. The owner-supplied linens are of top quality throughout. All beds have Simmons Beauty Rest "Recharge" mattresses. Great family room fitted with lots of comfortable seating has a 65 inch flat screen TV for family movie night or to watch the big game. The recreation room includes another 65 inch flat screen TV, SONY PSS, foosball table, ping pong table, darts and many games. The children will love it as well as the kid in you! Cable TV, wireless high-speed internet, and phone are all included. This house is master chef ready, with a huge kitchen, two sinks, two dishwashers, two refrigerators, an ice machine, and all the gadgets including a Kitchen Aid mixer.

    Want a beach fix? Tampa Bay beach is just a short stroll away as well as the Pine Ave shopping and dining. The Gulf of Mexico is just short blocks away. Sunsets on one side, Tampa Bay wide open views on the other - what better sights are there? Starting making this your perfect spot to come back to year after year and make a lifetime of memories. Ask for "My Sister's Beach House" when calling Island Real Estate to reserve your fantasy vacation spot!

    Amenities include elevator, wireless internet access, 4 car garage, 2 driveway, washer/dryer, laundry room, open patio, boat access on canal, heated pool & spa, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King | Bedroom 4: King | Bedroom 5: 2 Twins | Living Room: Queen & Twin Sleeper Sofas.

    Square Footage: 5700 Square Feet.

    We went to My Sisters' Beach House for an extended family trip. We had four adult couples who all had private bedrooms and plenty of space to hang out together or have privacy. The house itself is even more beautiful than the pictures! It is decorated and supplied with the best of everything. We woke up to our first day clouded with drizzly rain, but we spent the afternoon on the large deck playing board games and catching up, while enjoying the view. Other days were spent on the beach, at the pool, shopping, fishing, bike rides, walks and naps! Our evenings were spent either dining at wonderful local restaurants or grilling by the pool. (Too bad you don't get to go with my sister-in-law, who is an amazing cook!)! I can't wait to go back!

    Anna Maria
  • Living at the beach is like living anywhere else except it's BETTER in almost every way imaginable! You will enjoy the morning sun as it rises over the dock & canal and floods the living room with light. Experience it for yourself in 243 Willow Ave, Anna Maria Island. This beautiful 3 bedroom, den and 4 full bathroom is not your average beach house as it is a Frank Lloyd Wright inspired house. The screened in lanai wraps around the house from the pool/spa to the canal. Enjoy a day on the beach and come back in enjoy the brand new heated pool and spa. With room for up to eight people, you can bring the whole family and that includes the boat!

    The master bedroom suite is like your own private oasis. A separate to the new guest ensuite with queen bed and private bathroom overlooking the pool and spa. The canal front location allows you dock access and close proximity to the beach. But if you want to keep your feet on dry land for a day, you're also only a short trolley ride from some of the best dining and shopping in Anna Maria. Whatever you do, you can always come back and year after year. You won't want to miss a sunset and you are so close to the beach.

    Amenities include wireless internet access, driveway parking, washer/dryer, dishwasher, screened lanai, canal & dock boat access, heated pool and spa, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King | Den: Twin with Trundle.

    Square Footage: 2400 Square Feet.

    It was SO well equipped!

    Anna Maria
  • There’s a certain Florida way of life. It’s about knowing you need to enjoy every day and slow down so you don’t miss the sunset. Experience it for yourself and unwind in this Anna Maria vacation home located at 744 N Shore. With premium linens in three bedrooms and fluffy towels in two bathrooms, you vacation days will be a little brighter when you stay here. They don’t call it Sundance Cottage for nothing.

    There is room for up to six guests so whether it’s a girls week or family getaway, you’ll always feel cozy not confined. This light and airy vacation home is in Anna Maria right at the Gulf of Mexico. You’ll be just a flip flop’s walk to the beach and always within sight of it from your deck. Open a bottle of wine and enjoy a little time to breathe as the sun melts across the sky.

    Should there be a rainy day at 744 N Shore, you’ll be able keep the whole party entertained. Haven’t been able to catch up with your favorite show since the last season finale? Digital cable, surround sound, and a DVD player in the living room are all waiting for you and the popcorn. Music lovers have available a 5-disc CD player with iPod dock. And in the master bedroom is a laptop complete with printer. Wireless internet is available throughout for tablets or any other digital toys you may bring. Or maybe you’ve adopted a “life is simpler at the beach” philosophy and want to keep it low tech. Try old fashioned quality time with board games.

    Sunnier days can be spent out back. Your heated pool stretches out next to lounge chairs and table beneath swaying palm trees. Swimming all day builds an appetite so be sure you stocked up on burgers and kabobs for the Weber grill. If you’re not a barbeque fan, try whipping up something in the updated kitchen. With plenty of room for a holiday feast, Sundance Cottage starts to feel less like a vacation home and more like your own after you’ve made a few memories here.

    With so many island activities you might consider extending your stay. You can stroll seven miles of flour soft sand or take in the local art culture on Pine Ave. But you haven’t officially arrived in Anna Maria Island until you take a ride on the FREE trolley.

    Come see for yourself - stay for a week at Sundance Cottage and you will want to return again and again. Book with Island Real Estate today!

    Amenities include Wireless Internet Access, carport, Washer/Dryer, Open Decks, heated pool.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: 2 Twins.

    Square Footage: 1500 Square Feet.

    Very happy with our stay at Sundance cottage - have already booked for 2015.

    Anna Maria
  • Absolutely stunning in every way! This ultimate luxury beach vacation rental home is for relaxing with family and friends at the highly coveted north end of Anna Maria Island. It's just a short stroll from Bean Point beach and an easy walk to the Rod & Reel and City piers for fishing, dining or strolling.

    This custom built upgraded house features an open concept living room/kitchen/dining room and two bedrooms and a master suite all equipped with their own private ensuite bathrooms.

    The bedrooms and common living area are accessed through a fabulous surround glass paneled window walkway lined with custom blinds. Soaring ceilings and a rooftop skylight add to a unique design with beautiful porcelain tile throughout the house.

    The home is equipped with high speed wireless internet and unlimited long distance telephone to the US and Canada. The living room sits beneath a soaring cathedral ceiling with beautiful island palm ceiling fans which quietly move the air.

    The living room features modern classic furniture positioned around a unique two sided fireplace which can be enjoyed from every angle. A 42" flat screened TV and entertainment centre with surround sound allow for background music for dining and a HDTV and DVD player for a movie after dinner.

    Furnishings are a designer mix of modern classic designs and comfortable leather seating with coastal furniture accents. Unique artwork sets off the quiet sitting area tucked in by the fireplace. The dining room features a glass topped parsons table with 6 classic leather chairs.

    The kitchen will appeal to the gourmet cook in you with custom designed cabinetry, built-in appliances and gleaming granite countertops and breakfast sitting area to enjoy a leisurely cup of coffee. Everything is here for you to prepare and enjoy the perfect meal.

    The master suite is light and airy with a soaring ceiling and a soothing view of the pool area. It comes complete with a queen sized bed, walk-in closet and ensuite bathroom with a bathtub, 2 sink vanity and a walk-in shower spa. There is a flat screened HDTV and DVD player and a desk space for your computer. The second bedroom has a queen sized bed, its own private ensuite with shower and a combo TV/DVD unit.

    The third bedroom comes complete with two twin beds, is decorated with island flair and has its own private ensuite with shower. There is a flat screen TV, and for the kids -or the kid in you- a PlayStation 2 is already hooked up and ready to play games (provided) or DVDs . Lush tropical landscaping surrounds this exquisite home.

    Outdoors you will enjoy island lifestyle around the private pool with state of art salt water conditioning which is easier on your skin and bathing suits! Once you try a non-chlorinated pool you will never go back!

    There is an umbrella table with chairs and lounging chairs surrounding the pool and of course a gas barbeque for dinners outdoors. Walking Tour: As you enter the home, turn to the left in the open glass hallway, past the mermaid and enter the open concept living room/kitchen/dining room overlooking the front of the house.

    Walking through this area to the opposite side and turning right, will take you to the powder room and then taking a few steps more, into the second bedroom with a queen sized bed. Going back the way you came to the mermaid, the next door on your left takes you into the third bedroom with the twin beds.

    Continuing down this hallway, you enter the spacious master suite which takes up the whole end of the house overlooking the pool. There is a winding staircase in this room that takes you to a separate inside garage entrance and out to the pool area. It also serves as a secondary emergency exit.

    Amenities include wireless internet access, 2 car garage + driveway, washer/dryer, heated salt pool, dishwasher, glass enclosure lanai.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Queen | Bedroom 3: 2 Twins.

    Square Footage: 2100 Square Feet.

    This Home is absolutely stunning! The vaulted ceilings and dream kitchen were beyond our expectations. The photos don't do the home justice, since you have to be there to experience the comfort, ease, and luxury that is found at 619 Rose St. It's a short walk to Anna Maria's most beautiful beach and the Rod and Reel restaurant. the lush vegetation and beautiful pool add to the relaxing vacation feel that this home offers. Just sublime!

    Anna Maria
  • Located at the prestigious north end of Anna Maria, Blue Waters is a beautiful private resort-style villa, just minutes away from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops, restaurants and bars of Pine Avenue.

    Situated on a peaceful residential street, Blue Waters offers a lovely canal water view, private dock with brand new boat lift and easy access to the intra-coastal waterway. An oversized heated pool featuring a shallow water lounge and heated spa is perfect for relaxing as you admire your surroundings.

    Offering the best of both outdoor and indoor contemporary living, the landscaped back yard has a poolside lanai and terrace with upscale loungers and umbrellas, a giant-sized hammock, dining table with eight chairs and a large flat screen TV. Cook out on the Weber gas grill/barbecue or relax on the swinging seat which hangs in the shady branches of the magnificent Rosewood tree.

    The poolside office will allow you to catch up on any pressing business matters, before enjoying the rest of your day by the pool. Extending the entire length of the back of the home is a fabulous second floor terrace equipped with rocking chairs, sofas and tables, ideal for breakfast or an evening glass of wine while watching the sunset and local wildlife.

    Blue Waters light and airy interiors will also delight you.  The owner's attention to detail has created a spacious, superbly appointed home away from home. For those who love to cook, the fully equipped chef's kitchen includes KichenAid professional grade appliances and a six burner cooktop inlaid in a large granite island with wine fridge. A convenient Laundry room houses the full size Maytag washing machine and Maytag drier. An abundance of French doors throughout the home, with every bedroom having its own entry to the outdoors, makes each suite feel like a private oasis.

    Two extra large living areas provide plenty of room for the whole family to enjoy themselves. These boast top of the range furnishings, including large flat screen TVs, DVD players, a music and speaker system allowing listening throughout the house and there is even a full size billiards table. High-speed internet, cable TV and flat screen televisions in every bedroom complete the entertainment experience for guests.

    Superbly located and meticulously maintained, Blue Waters sleeps eight in the comfort and privacy of their own bedroom suites.  It has a two vehicle garage, plenty of guest parking and bringing your own boat is easy with the private dock and lift.

    Amenities include wireless internet access, 2 car parking spaces, driveway parking, washer/dryer, open patio, car garage, heated pool & spa, boat dock & lift.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Queen | Bedroom 3: Queen | Bedroom 4: 2 Twins.

    Square Footage: 3234 Square Feet.

    We have just enjoyed a wonderful vacation at Blue Waters. This is a lovely, stylish and spacious house, which we found extremely comfortable, well equipped & with excellent support from Island Real Estate. We have rented vacation homes in various parts of Florida over the past 20 years and this is easily the best. We really enjoyed the lovely pool and hot tub and the great canal-side setting. The master suite is lovely, with a gorgeous bathroom and spacious dressing room and the bedroom opens onto a nice balcony to enjoy our morning coffee. Anna Maria is a lovely island and the North end, where Blue Waters is located, really has a village feel to it. It's just a short stroll to the beach, to the Pier and to the great shops, cafés and restaurants of the Pine Avenue area. We hired bikes for a week, easy cycling and we really enjoyed exploring all the back lanes & spotting the abundant bird life. We certainly hope to return soon!

    Anna Maria

See Our Other Locations

See All Locations
Or
View Your Password By signing up, I agree to VaycayHero's Terms of Service & agree to join our mailing list for special offers and travel tips.
×
Or
×

Forgot Password?

×

Our concierge specialist is standing by to help you with your booking.
Call 888-733-2964 .

×
Filter