Holmes Beach Vacation Rentals
View Top Destination Searches
Rental Type
Search Radius
Surrounding Areas

Click the pins to select or deselect an area.

Condo Complex
Apply Filter ×

Holmes Beach 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

1157 rentals are available

  • 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
  • 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
  • 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
  • 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
  • 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
  • “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
  • 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
  • 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
  • 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
  • All of the Palm Isle Villages are a good choice for family vacations.  But PIV 3206 is particularly perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa.

    Being part of our Premium Linens Programs means PIV3206 is stocked with hotel quality towels and sheets. A week here with the people you love most is guaranteed to offer memories that last a lifetime.

    Each vacation cottage has its own courtyard with plenty of privacy from tall fences. In PIV 3206, you will find a propane grill, sun loungers, and an outdoor dining set to enjoy dining alfresco. Don’t worry about stocking up on propane – should your tank run out, Island Real Estate will provide a replacement. Just give us a call at the office.  Access to the courtyard is available through each of the bedrooms so if you can’t sleep away from home, just head outside and listen to distant crashing waves.

    Amenities include wireless internet access, assigned parking, washer/dryer, large private patio, heated pool, premium linens.

    Bed Configuration: Bedroom 1: Queen | Bedroom 2: Short Bunks | Living Room: Sleeper Sofa.

    Square Footage: 687 Square Feet.

    This property is very versatile for both a family vacation or a romantic getaway. The unit is super clean and tastefully decorated. To have access to the pool and the beach within walking distance was priceless for the kids. Guest services was also very responsive to all our needs.....Definitely coming back next year!

    Holmes Beach
  • DIRECT GULF FRONT cottage in Holmes Beach! When we say that Sea la vie is right on the beach, we mean one step off the back porch! Open the windows and fall asleep to crashing waves. Sea gulls and sunlight will be your alarm clock – that’s just how island time works, nd that’s exactly what time you’re on during a holiday at Sea La Vie.

    Sea La Vie is also located near some of the best loved restaurants on Anna Maria Island, but there will be days when you just can’t leave the cottage. The water will shimmer, you’ll get comfortable under the umbrella with a good book and before you know it, the sky is once again turning into a kaleidoscope sunset over the Gulf of Mexico, and when that happens, there is a charcoal grill and updated kitchen available for you to enjoy home cooking on your beach holiday. No need to go hungry just because you fell under the spell of island life.

    While you might feel a thousand miles from reality in this vacation rental, the real world does still exist out there and wireless internet will keep you connected to it, or escape from it even further by cuddling up with a movie on the living room’s flat screen.

    But there are some can’t miss spots on the island that are not within walking distance of Sea La Vie. A stop for the island’s free, air conditioned trolley is though! Ride it down to the north end of the island for boutique shopping on Pine Ave or fishing off the Rod and Reel Pier. Learn fun trivia about the area from your tour guide. Do you know which famous cookie was invented right here on Anna Maria Island? You will by the end of your ride around on the trolley.

    The real charm of Sea La Vie is its simplicity. Good company, plenty of sunscreen, and an iced drink for the patio are all you’ll need for a dream beach vacation. Come spend a week here and find out what it really means to get away from it all.

    Amenities include Wireless Internet Access, 2 parking spaces, shared Washer/Dryer, Open lanai.

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

    Square Footage: 600 Square Feet.

    This was our 2nd time at this rental. Hope to stay here again next time!

    Holmes Beach
  • Fantastic new private vacation rental home with outstanding Gulf Views from four balconies and large heated pool equipped with Tiki hut in tropical paradise setting. Ample seating will ensure everyone can relax and enjoy the extra large back yard and pool. Your outdoor paradise is equipped with a wet tiki bar, a swimup tiki hut and barbecue.

    Indoors you will find a ground level storage room equipped with a foosball table and ping pong table perfect for a little friendly competition during your holiday. This will be the ideal home for an intimate wedding or family reunion. This home is perfect for entertaining.

    Large dining room table comfortably seats 8 with 10 optional. Almost every bedroom and the living room is equipped with a flat screen television. To satisfy the high tech enthusiast the 2 master bedroom suites and living room offer high definition viewing.

    The living area also contains BlueRay DVD viewing. Surround sound is available in the living room, dining room and tiki bar. Did we mention the Wii Console (Playstation 3 may be coming soon!) that is perfect for the child (or adult) in your life that cannot live without video games which also doubles as the BlueRay player. Wireless internet provided for your convenience.

    This is a perfect retreat just half a block to the Gulf of Mexico in Holmes Beach. 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! Detailed layout: As you enter Almost Gulf through the foyer, there is a door to your right that will lead you to the garage, through the game room and to the gorgeous pool area.

    The garage provides guests with beach chairs, and a couple beach umbrellas. The game room is lots of fun providing a foosball table and a ping pong table! The pool area is very tropical and relaxing with an outdoor kitchen and a swim up tiki bar in the pool! Up the stairs to the first living level, directly in front is a powder room with a full washer and dryer beyond a pocket door. To the left of the stairway is a large living room, kitchen and dining room. Through the French doors off the living room and dining room there is a large balcony over looking the pool. To the right of the stairs, you will see two king bedrooms with a connecting master bathroom and a walk-in shower.

    Up the stairs to the second living level, straight ahead you will find a den with a trundle bed (two twins) that could also be used as an additional bedroom. To the right, you will see a master suite with king bed and a master bathroom and walk in shower and a balcony beyond the French doors. To the left of the stairs, as you are walking down the hall, you will see a shared full bathroom with a tub/shower combo. Beyond the bathroom, you will find two more bedrooms; one is a full size bed and the other is a second master with king size bed and a master bathroom with walk in shower.

    Amenities include heated pool with spa & tiki, 4 balconies & patio, washer/dryer, 4 parking spaces, wireless internet access.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: King | Bedroom 4: King | Bedroom 5: Queen | Bedroom 6: 2 Twins | Living Room: 2 Sleeper Sofas.

    Square Footage: 2546 Square Feet.

    We had a wonderful time !

    Holmes Beach
  • This home is a restoration of an original vacation home to fully updated Florida codes and standards in all respects.  This 3 bedroom 2 bathroom ground level vacation rental single family home awaits the vacationer in you. The new salt water heated pool and spa has a baby sundeck with umbrella and plenty of outdoor seating. The large grass lawn area will let you play pitch and catch and soak up the Florida sun.

    It is an authentic Mid-Century AMI vacation home constructed in 1953 and was occupied by the original owner’s family up until 2013. The renovation was professionally designed and detailed inside and outside to provide a unified and period appropriate charm.

    This home is located on a quiet street and it has a European flair with its exposed wood post and framing to its design. This island home is just picture perfect inside and out and entirely done with top of the line furnishing. Just a short stroll to the sugar sand beaches on the Gulf of Mexico. You don't want to miss a sunset!

    Amenities include wireless internet access, driveway, washer/dryer, heated pool & spa salts, premium linens.

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

    Square Footage: 1200 Square Feet.

    Very nice house. Love work with Vaycayhero team.

    Holmes Beach
  • Enjoy this new elevated vacation rental home with private lagoon style pool with lush tropical plants about two blocks to the beach in Holmes Beach. Fashionably yet comfortably decorated living room offers big comfy furniture centered around a new 50" flat screen TV with Blue Ray/DVD player where you can enjoy a game or movie.

    The large open kitchen with granite counter tops, breakfast bar and dining area offer plenty of space for family gatherings to enjoy a special meal together. The private master bedroom is furnished with a king sized bed, large closet and master bath with jacuzzi style tub and walk-in shower.

    Two other guest bedrooms offer both a king or a queen sized bed and the fourth bedroom offers 4 twin/bunk beds. Each bedroom is equipped with flat screen TV's and DVD players. Located directly off the living area is a private wash room with washer/dryer laundry facilities.

    This vacation rental also offers an elevator which is handy for bringing up luggage or groceries. Sit outside around the beautiful pool with brand new patio furniture. You can watch your family swimming, enjoy a meal after cooking on the new gas grill or curl up with a good book and enjoy the Florida sea breezes.

    This lovely home is just a short stroll to many restaurants, shops and the free trolley stop. It is a wonderful spot to spend some quality time with your family, friends or just that special someone in your life for a perfect island get-away.

    Come and spend your holiday here on Anna Maria Island, and you may never want to leave. Walking Tour: As you enter the home through the spacious foyer, you will see a staircase straight ahead that leads you up to the first living level. On the first living level, you will walk right up to the half bathroom with a pocket door that opens up to a full size washer and dryer laundry room.

    To the right of the stairs, you will find the lovely spacious floor plan, including the kitchen, living room and dining room. Off of the living room, there are French doors leading you to a large open-air balcony that over looks the beautiful pool area. Down stairs in the pool area you have a table and chairs that are pool side and lounge chairs to lay out and soak up the island sun.

    The pool is set in a tropical setting with lush landscaping. To the left of the staircase, you will find a master suite with a connected master bathroom with Jacuzzi tub. Up the second staircase, you will find a comfortable seating area which is also a sleeper sofa for additional sleeping. You will also find the three additional bedrooms.

    You have another king master bedroom suite with a large master bathroom including a Jacuzzi tub and a walk in shower, a queen bedroom and the fourth bedroom has two sets of bunk beds which are twin sized. There is also a full bathroom off of the hallway for main use. This property comes equipped with an elevator for your convenience.

    Amenities include elevator, wireless internet access, 2 car garage, washer/dryer, open porches, heated pool, dishwasher, elevator.

    Bed Configuration: Bedroom 1: King | Bedroom 2: King | Bedroom 3: Queen | Bedroom 4: 4 Twin Bunks | Living Room: Sleeper Sofa.

    Square Footage: 2600 Square Feet.

    Almost new-great realtor booking experience!

    Holmes Beach
  • Refreshing and tropical are the perfect ways to describe this vacation rental home Mango Breeze at 141 50th Street! Spend a week here in Holmes Beach and get the taste of island life on your tongue.

    Spend a beach holiday on Anna Maria Island in 2,500 feet of style and luxury. There’s room for the whole family and this does include Fido. Eight guests and dogs up to 25lbs can fit comfortably in the property. Wooden floors spread out across four bedrooms, all of which have beds made up in premium linens. Every room has that little extra touch of class – from granite countertops in the kitchen to sunken tubs in the bathrooms.

    Some vacation rental homes have it all and some, like Mango Breeze, have more than that. Flat screen TVs, wireless internet, and updated appliances keep you plugged into modern times but there’s plenty of old fashion ways to distract you from reality. Paradise can be found in a good book and glass of wine on your patio. There’s even a family game room with ping pong tables and four bikes available to use during your stay! Just call us at the Island Real Estate office for details.

    The backyard is an oasis all its own for the days when you just want to stay poolside with loved ones. Whip up some pina coladas in the thatched roof bar. Watch how the sun soaks over lush bromeliads and palm trees. Get comfy on one of several lounge chairs and you can join them. The pool is also heated so no matter what time of year you visit, you’ll be able to dive into indulgent island living.
    Being west of Gulf Drive means you won’t have any busy roads to cross. Just slip on your flips flops and wander towards the beach whenever you like. Our sand glitters with quartz and the waves are calm, gentle lulls. But the best part is, staying in a vacation rental home this close to the Gulf of Mexico means you never have to miss a sunset. For anything not within walking distance, hop on the local free trolley. It will take you wherever you need to go in air conditioned comfort.

    There are too many fabulous features to mention - you will just need to try them out for yourself during a holiday. Stay for a while in Mango Breeze and take a bite out of life on Anna Maria Island. Book with Island Real Estate today!

    Amenities include wireless internet, car garage, washer/dryer, open porches, heated pool, premium linens, pet friendly - 25lbs(no cats).

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

    Square Footage: 2040 Square Feet.

    Enjoyed our time immensely great house for a family reunion such as we had!

    Holmes Beach

See Our Other Locations

See All Locations
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.

Forgot Password?


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