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Sarasota Vacation Rentals

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Lana H. VaycayHero Guest

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  • It’ll be hard to miss the style, taste, and indulgence waiting for you at this three story, Holmes Beach vacation home. From the moment you pull into the driveway and spot that distinctive and invigorating coral color we love so much in Florida, you’ll know a week of cushy comfort and relaxation is waiting for you. Even travel between floors is made easier with your private elevator.

    This is a perfect retreat just one and a half short blocks to the Gulf of Mexico offering limited but still lovely peeks of the water. (5) Bedroom, (3.5) Bath, accommodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. This vacation home will allow you to reconnect with family or friends and provide for memories that will last a lifetime.

    As you enter the foyer and go up the first staircase of the home you will find a powder room straight ahead with a full sized washer and dryer hidden behind a pocket door. To the left of the staircase, you will find the spacious living room, kitchen and dining room with a dreamy and sundrenched balcony.

    Coral Reef is perfect for entertaining so we hope you’ll consider it during Thanksgiving and Christmas or any other holiday should be spent with the whole family. Large dining room table comfortably seats eight with room for ten total.

    Through the French doors of the living room and dining room, there is a sweeping balcony that overlooks the pool area. To the right of the staircase you will find your first master suite with a king size bed and a master bathroom with a Jacuzzi tub for you to soak. There is also an elevator for your convenience that leads you from the foyer up to the second living level of the home for help with luggage and visitors that might not be as comfortable on stairs.

    On the second living level, straight ahead you will find a den with queen sleeper sofa which is considered the 5th bedroom for visitors.  To the right of the staircase you will find a second suite with attached bathroom and stand up shower. To the left of that staircase, you will find another full sized bathroom, followed by twin and queen bedrooms.

    Every bedroom and the living room are equipped with a flat screen television. Both master bedroom suites and living room offer high definition viewing with Blu-Ray and DVD. Surround sound is available in the living room, dining room and tiki bar. Did we mention the Playstation 3 that is perfect for the child (or big kid) in your life that couldn’t bear to leave video games back at home. Wireless internet provided as well as free long distance within the continental United States.

    Ample outdoor seating ensures everyone can relax and enjoy the extra-large backyard and pool together. Your personal oasis is equipped with a wet tiki bar and barbecue fror the ultimate dining alfresco experience. The vacation rental also provides a dart board and ping pong table, perfect for a little friendly competition during your vacation.

    Amenities include Wireless Internet Access, Garage, 3 parking spaces, Washer/Dryer, Dishwasher, Elevator, Heated pool, Pet Friendly.

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

    Square Footage: 2690 Square Feet.

    What a sad day when we had to leave "our" beach house. We have been lucky to travel all over and Anna Maria was a perfect spot. The house was truly everything you need in a perfect beach house. We can't wait to return.

    Holmes Beach 16.74 miles
  • 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 17.95 miles
  • 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 17.73 miles
  • 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 17.58 miles
  • BRAND NEW Custom-built Island Home located at 111 81st Street! This fantastic vacation rental home is just a few houses to the white sandy beaches of Anna Maria Island and the Gulf of Mexico. Enjoy the large heated pool that boasts a cascading rock waterfall and hot tub all in a tropical paradise setting! Take the spiral staircase to the roof top deck for great views of the Gulf and enjoy a sunset.

    On the main living level there are 2 full bedrooms both with king beds in an area with double doors that closes off from the living room - great for late sleepers! There is also a den/5th bedroom that has two large chairs that open into twin sleepers. One full bath and a powder room are also on this level. Upstairs are the two master suites, both with king beds. Each has their own large luxurious master bathrooms. This home is a perfect vacation choice for extended family groups.

    Your large outdoor tropical paradise is equipped with ample seating for everyone. There is a dining area, chaise lounge chairs, barbecue, and even a television and luxurious outdoor wet bar with sink and built-in refrigerator! Outdoor speakers with an iPod option will allow you to sunbathe to your own playlist. You will also be able to have fun playing pool during your holiday poolside.

    The large dining room table comfortably seats 8 with an additional 4 at the gorgeous granite counter bar. Every bedroom has both a flat screen television and is equipped with an alarm clock that has an iPod plug in. The living room has a 60 inch LARGE flat screen HD TV with DVD player that also plays CD's. The 5th bedroom/den has a game station to enjoy.

    This is a perfect retreat and just a very short stroll to the Gulf of Mexico in Holmes Beach, just a short stroll past a few houses from the beach with no roads to cross. This home will allow you to reconnect with family or friends and should provide for memories that will last a lifetime. Sounds like a fabulous vacation - reserve your holiday now!


    Amenities include wireless internet, 5 parking spaces, Open roof top deck, washer/dryer, heated pool & spa, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King | Bedroom 4: King | Bedroom 5: 2 Twin Sleeper Sofas.

    Square Footage: 3000 Square Feet.

    The TV's and the den furniture are all GREAT. Very comfortable!! The master bedroom bed is very comfortable too, the kitchen was easy to work in and had everything we needed. The pool are was very nice as well!

    Holmes Beach 17.46 miles
  • Enjoy spacious Florida glamour with a week at this three bedroom, three bath vacation townhome. (3) Bedroom, (3) Bath, accomodates to (6) people: 1 King, 2 Queen. Outfitted with lighthearted colors on the wall and designer quality furnishing, you can enjoy all the luxury of hotel living without having to sacrifice any of the intimacy or privacy of home.

    The whole family can get away from it all on the top floor of this condo building located less than two blocks from the Gulf of Mexico beaches. Elevators are ready to help with luggage and guests that might have difficulty with steps. Six people can relax comfortable in the townhome, plus the family pet – dogs are welcome with a deposit to relax by your side for a dream vacation at Villa de la Playa in Holmes Beach.

    Upon your arrival to this elevated vacation home, you might need to take a moment and soak up how the sunshine looks pouring over granite countertops in the kitchen, a rich wooden dining table, and gulf coast inspired graphic print fabrics in the living room. Everything is styled with an eye for taste and luxury. Updated appliances for chefs in the family include a flat top stove, microwave, and dishwasher. Get comfortable and catch up with loved ones over coffee at the breakfast bar or have a movie night in front of the living room’s 42” Plasma flat screen. No matter where you’re comfortable in this townhome’s open great room, you’ll be able to enjoy togetherness and your own territory.

    From your fabulous vacation rental, you’ll be able to spot peeks of the cerulean sea waters and a stunning view of the pool deck downstairs. Kids will love days of playing Marco Polo while grownups will enjoy soaking in the hot tub with a sunset streaking across the sky. The walk to the beach will take less than ten minutes but if you want to explore Anna Maria Island further, another quick jaunt will take you to a stop for the island’s free, air conditioned trolley. It circles daily around Anna Maria, Holmes and Bradenton Beaches; a great way to make friends with some locals who will let you know their favorite spots for dining and shopping on Anna Maria Island.

    This is a multilevel townhome. This property has its own private pool.

    Amenities include elevator, wireless internet, washer/dryer, rooftop terrace, Car garage, heated pool with spa, premium linens, No cats.

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

    Square Footage: 2376 Square Feet.

    I will run out of text before I can completely describe how much we loved this house. Lots of room, pool was great, and location was fantastic -short walk to the beach and short trolley ride to lots of restaurants. Beautiful view of the Gulf from the rooftop patio. Fully stocked with dishes, etc. And extras like a stereo in the house, with speakers by the pool. Very comfortable throughout the house. We are seriously considering renting this house again next year. If you are considering it, you will not be disappointed. And the people at Island Real Estate are fantastic to work with. The whole experience was a 10+

    Holmes Beach 15.5 miles
  • Seabreeze Cottage is coastal living chic at its best! This huge one bedroom, two bath cottage with a detached guest suite is located at 103 Highland Avenue in the historic Bridge Street neighborhood of Bradenton Beach.

    The gorgeous beach is just about 60 yards or so down a quiet street, turn the other way and you are at the fishing pier. Unique shops, great restaurants, trolley and library are right around the corner. The Seabreeze Cottage has undergone a complete makeover during the past year and is just perfect for a getaway to the beach. Every part of this cottage is tastefully decorated.

    It features an upstairs master suite with a separate seating area, with a loveseat sleeper that is perfect for a small child, and a full bath and deck with views of the bay. Downstairs is a beautiful new kitchen, living room with a comfy thick queen futon and full bath with a large covered deck. There is a completely separate guest suite that features two full size futons and a full bath. Evening get together in the private, fenced back yard are a must.

    The kitchen is fully equipped with everything to cook up that special sunset dinner. Compact washer and dryer included, as well as off-street parking. There is a 39” television in the living room and a 14” television with a DVD player in the guest suite. Wireless high speed internet with expanded cable and free domestic long distance calling is provided. Extras include a BBQ grill, bikes, coolers, beach chairs and fishing poles.

    Amenities include BBQ grill, internet access, dishwasher, patio or deck, washer and dryer in unit.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: 2 Full Size Futons | Living Room: Queen Futon

    Excellent location! Close to beach, pier, restaurants , Bridge street. Etc. Very clean and beautifully decorated house! I would definitely book again here and would recommend this rental for anyone looking for this area! Thank you so much for a memorable vacation!!!

    Bradenton Beach 13.61 miles
  • There’s as much to love inside the vacation condo as there is inside. Hidden Cove #6 has two bedrooms, two and half bathrooms with room for up to four guests – all outfitted in premium, hotel quality sheets. Little touches of luxury can be found throughout from the updated, stainless steel appliances in the kitchen to the master king bed’s whimsical canopy. Free wireless internet is provided.

    Be sure to get home in time for the sunset, you’re going to have one of the best seats in the house! Not only does your personal wooden deck provide easy access to our flour soft sands, you’ll be front row center for the nightly show that is sunset. You haven’t really arrived in Florida until you watch the sun melt below the horizon and the sky burst into a kaleidoscope of gold, red, and magenta. The living postcard panorama extend to the master bedroom as well – open sliding glass doors at night so you can wake up to the song of seagulls in the morning.

    Amenities include wireless internet access, 2 parking spaces, assigned parking, washer/dryer, dishwasher, open deck, pool.

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

    Square Footage: 1456 Square Feet.

    We enjoyed our stay very much and will deginately be back!

    Holmes Beach 16.53 miles
  • Know what it really means to have the world as your oyster by spending your next holiday at Island Pearl on Anna Maria Island. Eight guests can spend a week in this luxury vacation rental with everything you’ve wanted and more.

    Wander through the ground level home and you’ll find touches of extra pampering.  Feel the sheets, bath and beach towels – those are professionally laundered and premium quality linens! You also might notice that four bedrooms and bathrooms means minimal sharing. An extravagance that many of us never get to indulge in back home.

    Exuberant coral, sea foam, and burnt sugar brown walls will put you into the Florida frame of mind from day one in your luxury vacation rental. Watch sunlight pour through the windows and over vaulted ceilings, hardwood floors and a spacious, open floor plan.  Everyone will have room to spread throughout the property, while enjoying quality time together.

    The living room will be taken over by techno buffs to enjoy a wall mounted flat screen with DVD player and a Sony PlayStation. Family chefs will enjoy a well-stocked, updated kitchen with stainless steel appliances. Before you know it, everyone will belly up to the breakfast bar for a taste of home cooking on vacation.

    Also provided at the vacation rental are beach toys, chairs and an umbrella. This comes in handy considering how close you are to the Gulf of Mexico. A short walk across Gulf Dr. takes you to those soft, glittering sands you’ve been daydreaming at work about.

    If you decide you want to stay close to home for the day, there is plenty of relaxation to be found in your own backyard. Take a few laps around the shimmering, heated pool (don't forget about the spa, too!) and then settle into a cloth hammock. Just be careful - with a good coastal breeze swaying you and the palm trees overhead, a quick nap could last all afternoon and you’ll be burnt to a crisp. Wake up in time to reapply your sunscreen and enjoy a cookout on the poolside propane grill.

    Amenities include wireless internet, 2 parking spaces & driveway parking, washer/dryer, heated pool & spa, premium linens.

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

    Square Footage: 2300 Square Feet.

    We just returned from a wonderful holiday with our kids and their new baby, staying at Island Pearl. What a wonderful week it was! The house is so beautiful - inside and out - and no detail has been spared to make it comfortable and inviting. The decor is so lovely and 'beachy' in a very upmarket way. We've rented several homes on the island over the years and liked certain things about them. But this house was our favourite - it had it all. The well laid out bedroom design allowed for privacy. So many beautiful bathrooms! We loved the backyard and used the pool, hot tub and hammock every evening. This home is a real gem. We'd love to visit again!

    Holmes Beach 17.33 miles
  • “Sandy Pants” is a chic multilevel Anna Maria vacation rental home with coastal flair and everything you need for the perfect Island vacation! Accommodating up to 5 guests “Sandy Pants” offers 2 bedrooms and 1.5 bathrooms with 1 king bed, 1 double bed, 1 twin bed and 1 sleeper sofa making it ideal for families as there’s something for every  age, style and sensibility.

    When you arrive at “Sandy Pants” the first thing you’ll notice is the distinct sense of style. The chic beach decor is tasteful, fun and perfect for the island atmosphere. Animal print rugs sweep out across the living room floor which is equipped with a large wall mounted flat screen, well stocked bookshelves, and wireless internet throughout. A mural of gently rolling sand dunes will inspire you to lay back in the plush oversized chair big enough to nap, meditate or read in the sun room. On rainy days enjoy the game room complete with game consoles!

    Whip yourself up a snack or whole meal in the updated, sparkling white kitchen. A flat top stove, dishwasher, well stocked shelves and drawers provide everything you need. Take meal time outdoors, and utilize the propane grill and al fresco dining area.

    This Anna Maria Island vacation rental home boasts an amazing private pool paradise complete with heated pool, lush green landscaping, babbling waterfall, hammock swing, enclosed outdoor shower, comfortable furnishings and plenty of room for everyone to relax.

    “Sandy Pants” is located West of Gulf Drive with no roads to cross for the Gulf of Mexico’s calm, azure waters. Just grab your towel, load up the water bottles and snacks, apply sunscreen early and take a short stroll down White Avenue with no busy roads to cross.

    Amenities include in wireless internet access, 2 parking spaces, washer/dryer, heated pool, premium linens.

    Bed Configuration: Bedroom 1: King | Bedroom 2: Twin & Double.

    Square Footage: 1708 Square Feet.

    We're looking forward to our next stay.

    Holmes Beach 17.54 miles
  • The fully equipped outdoor barbecue kitchen with a built-in refrigerator and dining area offers plenty of space for a family get together. The outdoor sound system with an iPod and iPhone option will allow you to sunbathe on one of the many chaise lounge chairs while listening to your own playlist. An outdoor TV allows you to watch your favorite TV show or sports event while relaxing in the hot tub or pool. Right next to the pool you will also be able to play a fun game of giant chess with your family.

    In front of the house our large circular driveway offers enough space for at least six cars. There is enough room for you to bring a trailer with your personal sporting equipment or your own jet ski or boat. Public boat ramps are available in short distance from the house and ready for you to make your ultimate boating experience on the Gulf of Mexico.

    The ground level house with its wide doors and barrier free showers makes it easy for all ages to enjoy.  The newly remodeled home is fully insulated and not only fulfills all the ecological standards, but provides a beautifully quiet atmosphere. Inside, the open floor plan flows from the large kitchen and dining area to enormous seating in the living zone-great room. The kitchen is furnished with modern appliances that allow you to prepare either a small snack or a large family dinner. Use our high quality WMF pots, pans and cutlery to prepare a delicious meal. For special occasions you can set the table with our exclusive Villeroy & Boch China and cutlery. You will find QR-Codes on every technical appliance that lead directly to the online instructions. The cooking island with a ceramic glass cooktop offers the opportunity to talk with your guests while cooking. The open design invites everyone to get involved.

    In the evenings you can spend time on the large couch having a chat with your family and friends, listening to CD‘s or watching TV or DVDs on a huge 80 inch full HD flatscreen TV. Enjoy the power of a full Dolby Surround System. From the living area you have a perfect view of the kids playing in the den. Through a glass door you can have an eye on them while enjoying the quietness of the area.

    The den offers plenty of space for your kids to play. They can lounge in a Fatboy bean bag or relax on the sleeper sofa while having a game with their friends or siblings, having fun with our Playstation 4 or watching TV on the flatscreen.

    Grant yourself this wonderful retreat just a few steps from the Gulf of Mexico on Anna Maria Island. This home will allow you to reconnect with family or friends and should provide for memories that will last a lifetime.

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

    Square Footage: 3000 Square Feet.

    Perfect The house was perfect. We had a family reunion and the house was perfect for us. Even though the weather did not cooperate (too cold) we had a great time, We enjoyed the jacuzzi and the patio are very much. I will definitively recommend this house for a family gathering

    Holmes Beach 16.15 miles
  • You'll be close to all the favorite things to do on Anna Maria Island while spending a week's holiday at this well-appointed vacation home! Private heated pool, free wireless, sorry no pets allowed, less than two blocks from the beach.Boat dock slip available just a short stroll to nearby Marina. Dock slip #8 has water,power and will hold up to a 27' boat.

    Wonderfully appointed island home vacation rental three bedroom and two bath single family home in a perfect Holmes Beach location close to the pristine beaches, choice restaurants and fabulous shopping experiences. All new furniture with a designer flare will make you want to come year after year. Well equipped kitchen with new granite countertops.

    Lush tropical landscaping makes you feel like Anna Maria Island is your own private island. Make our little island paradise your home away from home. So much better than hotel living in this vacation home.

    Amenities include wireless internet access, 2 space car garage, stackable washer/dryer, boat access on marina, heated pool, premium linens.

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

    Square Footage: 1650 Square Feet.

    The house was absolutely beautiful! The location was great just a quick walk to the beach and shopping. The pool was amazing. We had a perfect vacation. We had 4 adults and 2 children with us and there was more then enough room for all of us. The house felt like a home not a rental so much detail was put into every inch of the house. The pool and beach toys/chairs/umbrellas were great to have, there was even a wagon to pull all of the gear to the beach. WE would definitely rent here again.

    Holmes Beach 16.36 miles
  • 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 18.38 miles
  • Welcome to Coastal Sands! It time to slow down and drag your feet in the sugar sand beaches on the Gulf of Mexico which is just a short stoll away. This is especially true of a Florida vacation and a week at Coastal Sands on Anna Maria Island can show you just how sweet island life is. This vacation cottage has everything to offer with (3) Bathroom, (2) Bath, accommodates up to (8) people, an updated kitchen, and stylish fixtures and furnishing.

    Each bedroom and family room has a flat screen television and up to eight vacationers can fit comfortably at at this ground level single family vacation rental. The decor is tasteful, fun and perfect for the luxurious island atmosphere. The screened in lanai is a dreamy spot to enjoy your morning coffee or a balmy board game at night. Stay in the shade and air conditioning of a private sunroom and access the free wireless internet to work and play on your laptop; this room makes one heck of a sundrenched makeshift office.

    The easy beach walk requires just a coat of sunscreen, grabbing your towel, favorite beach gear and then a short stroll down to the Gulf of Mexico and those flour soft sugar sands people come from all over the world to see. Take an even easier walk to the oasis waiting for you right outside in the caged pool deck and backyard. Let the kids tucker themselves in heated waters while you stretch out by a palm tree, lounge chair, and beach book. Dinner cooked out on the propane grill will be even more delicious under one of those world famous Anna Maria Island sunsets.

    Anything else you need or want to reach is accessible by hopping on the free Island Trolley which loops around the entire area in a leisurely but air conditioned pace. What’s your relaxation destination? Boutique shopping and historical fishing sites such as the Rod N Reel in Anna Maria City? Stay in Holmes Beach to get buffed and polished as a pearl at day spas like Aqua Aveda Salon and Spa? Or maybe you want to put on those boogies shoes for a night of dining and dancing on Bradenton Beach’s Bridge Street.

    It’s completely up to you but however you want to unwind, the trolley can get you there. A marina is also nearby and if you’re interested in renting a boat, let us know. Island Real Estate has a few strings to pull for discounts available exclusively to our guests! There are so many things to do on Anna Maria Island you might need to extend your stay – it happens all the time once people experience the phenomenon that is love at first sunset. Once you take your holiday here you will never want to go back to hotel living!

    Amenities include Wireless Internet Access, Carport, 2 parking spaces, Washer/Dryer, Dishwasher, Heated caged pool area, Premium Linens.

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

    Square Footage: 1500 Square Feet.

    Very nice place. Great fishing and beach.

    Holmes Beach 17.02 miles
  • 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 18.7 miles

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