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Welcome to Cheerful Oasis – Your Bay-to-Beach Escape!Discover the ultimate island retreat at Cheerful Oasis, a delightful 2-bedroom, 2-bathroom condo perfectly situated for your next getaway. Nestled just off the walking trail to the Marina, Bridge Street, and Bradenton Beach, this serene haven...
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Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim’s Place restaurant and sports bar. This *ultimate beach...
Featured review
This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back
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110 11th Street South - Bradenton Beach - FL 34217No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...
Featured review
The house was beautiful, lots of space to spread out with a family of 12. Location was perfect, beach on one side and bay on the other. Had everything we needed for cooking, pool, and relaxing. Pool was...
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Unwind in this bright and breezy 2-bedroom, 2-bath condo just steps from the beach. Sip your morning coffee on the private balcony with peekaboo Gulf views, then head straight to the sand, shops, and dining — all just minutes away.Perfect for couples, families, or friends, this coastal retreat...
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Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside...
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WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants...
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Lazy Days at Runaway Bay is the perfect place to take time out and relax at your home away from home. This ground floor beach condo has been updated and features a lovely open-floor plan, 2 bedrooms/2 bathrooms, as well as a sheltered lanai with views out to the lush tropical garden and is only steps...
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The condo and communications was perfect. NEVER had one issue. Would highly recommend. Clean pool and community activities.
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Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your...
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Location is where it's at! Close to everything, yet on a quiet street. We had a great time celebrating 5 years post cancer! Loved the Island and everyone on it. We didn't want to leave! Loved the way...
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Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool. Upon entry, you will find the open...
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Our stay at Blue Lagoon was perfect. The condo was very clean and had absolutely had everything you needed. The beds were very comfortable. The private home pool was so relaxing and inviting.
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Charming 1-Bedroom Condo in Runaway Bay – Anna Maria IslandPrime Location – Steps to the Beach: - Located in the highly sought-after Runaway Bay community on Anna Maria Island - Just across the street from white sand beaches and crystal-clear waters - Walkable to shops, restaurants,...
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VRC16-000137 Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida.This ground level beach house offers 4 bedrooms,...
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This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing....
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Footprints in the Sand 114 48th Street Holmes Beach FL 34217 VRC19-000156 Welcome to FootPrints in the Sand, a stunning vacation home located just a short walk from the crystal clear waters of Anna Maria Island. This beautifully designed 4-bedroom, 3-bathroom retreat offers a perfect blend of comfort...
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NEWLY RENOVATED! Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground level canal front home has everything you need to make this your best Anna Maria Island vacation ever. This home offers a private heated pool overlooking the mangroves and canal, private...
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Conch-Out Beach House 303 68th St, Holmes Beach, FL 34217 VRC19-000273 | 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool + Spa | Pet-Friendly Completely Renovated February 2025! Welcome to Conch-Out Beach House, a beautifully renovated one-level bungalow that blends classic Florida charm with...
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This is a great house in a fantastic location. The close beach access is very convenient. There are 6 complimentary high quality beach chairs that came in very handy. There is even a handy beach wagon...
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Beach Bliss by Beach Retreats Vacation Rentals 320 64th Street, Holmes Beach, FL 34217 3 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Walk to Beach | Pet-Friendly Fully Renovated February 2025 Welcome to Beach Bliss, a beautifully updated 3-bedroom, 3-bathroom bungalow just...
Featured review
Outside patio was perfect! The pool and hot tub were great. Living room area was small but comfortable.
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VRC24-000077 Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated...
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VRC25-000069 Welcome to "Gulf Breeze" – Your Island Retreat in Holmes BeachLooking for your perfect island escape? "Gulf Breeze" is a bright and breezy 2-bedroom, 2-bathroom second-floor condo (Unit 208) located in the quiet and friendly Cayman Cay community in Holmes Beach...
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Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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Kai Blue is located in Holmes Beach, just steps from the beautiful AMI beaches. This 4 bedroom/2.5 bathroom with an elevator also has a private backyard with a pool. Kai Blue gives you the dreamy coastal vibe and it's close to restaurants, Island stores and right next to the free trolley stop.Pull...
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Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .​​​​​​Welcome to this beautifully renovated 2-bedroom, 2-bath condo...
Featured review
We stayed a week at Runaway Bay. We were very happy with our condo and the pool area. Good communication with Sea Breeze rental co. Very responsive via text We enjoyed our condo backing up to the intercostal...
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Walk in and be wowed — the Gulf of Mexico and sugar-white beaches are right in front of you! The view of the Gulf is across the street, where you'll see some of the best sunsets you'll ever see! It's truly breath-taking, and the best part? You get to experience it all, every day of...
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Very few beachfront vacation homes will get you as close to the sand as Hidden Cove #1— a beautiful 2-bedroom condominium with exquisite views and unlimited access to the aquamarine Gulf of Mexico. Located within a charming coastal community that also offers a crystal-clear swimming pool, your family...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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210 65th Street Holmes Beach, FL 34216 VRC17-000007 No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...
Featured review
Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed...
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When you arrive at the property you will notice ample parking for your whole party. When you enter the property, head up the stairs in the front of the home and enter your code.Once you enter you will see where the property gets its name, Crazy Mermaid! When you enter you will see off to the...
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Looking for a prime location to vacation? Seagrass Flats Unit 2 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops; vinyl plank flooring...
Featured review
I want to start by saying the accommodations were nice and the location is excellent. We would stay here again. The rest of my comments or for the rental company, owner and future renters. The check in...
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Brimming with historic character, this charming ground level 1 bedroom/1 bath cottage has a bright modern, organic feel–and is merely steps from the white sandy beaches. With dramatic vaulted ceilings and secluded garden settings, The Cozzi Cottage offers everything you'd want in a beach vacation....
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Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of Anna Maria Island. This home has everything you need for the perfect vacation and is only a short walk to the white sandy beaches. Upon entry, you have the living room where you can...
Featured review
We enjoyed our trip to Anna Maria. Very quant, quiet beach. Beautiful clear water and amazing sunsets. Can’t wait to go back!!!
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Wave From It All by Beach Retreats Vacation Rentals Holmes Beach, Anna Maria Island VRC23-000056 3 Bedroom | 2 Bath | Sleeps 6 Welcome to Wave From It All, your perfect island escape just steps from the sugar-white sands of Anna Maria Island. Whether you're sipping morning coffee on the porch...
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Welcome to Pink Pearl, your dream coastal retreat! This stylishly renovated one-story home combines tropical charm with modern comfort—perfect for families or groups looking to relax, entertain, and explore beautiful Anna Maria Island.The Space: - Spacious, single-story home with 4 bedrooms...
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Welcome to West O’ Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than ever! If you are ready for a relaxing stay on beautiful Anna Maria Island, then this is the beach house for you! This exceptional custom-built 4 Bedroom 3-bathroom house makes it easy...
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Island Escape by Beach Retreats Vacation Rentals 307 65th St, Holmes Beach, FL 34217 VRC18-000047 Your dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions....
Featured review
We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly...
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VRC22-000083 Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home...
Featured review
Everything was Perfect. The only thing I would change is to Stay Longer! Everything was wonderful. Location was perfect, the Beach, the Pool and the Restaurants.
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306 Clark drive (B) Holmes Beach, FL 34217 VRC17-000009 Dog Friendly! Beautiful open concept home. 3 king bedrooms with en suites and a den with 2 single bunk beds make this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the...
Featured review
Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.
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Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations,...
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Welcome to “Pineapple Cottage” – a beautifully updated ground-level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants, and fun on Pine Avenue. This charming cottage has been completely restored after hurricanes Helene and Milton. This...
Featured review
This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay...
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Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Featured review
Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.
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VRC17-000063 Welcome to “Coastal Breeze” on beautiful Anna Maria Island. This vibrant four-bedroom, three-bathroom island retreat is your perfect vacation escape on AMI. The backyard is a true highlight, featuring a private heated pool with spa, cozy and colorful seating areas, and a one-of-a-kind...
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Come relax and enjoy this stunning 2 bedroom/2 bathroom second level, recently updated condo at Runaway Bay. Runaway Bay is a bayfront complex that is less than a 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated...
Featured review
We really enjoyed our stay at Runaway Bay. The outside of the complex looks pretty dated but the condo was freshly renovated. We had everything we needed to enjoy our stay. We appreciated all the beach...
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Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers...
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Heated salt water pool. Baby and beach equipment, BikesStay, Explore, Relax! We've got you covered! This listing, A Lazy River Day and Night includes Both sides of duplex home.Cleaning fee includes Professional Linen Service for all towels and bedding!A leisurely stroll (less than three...
Featured review
Where do I start? This is a beautifully decorated with amazing location beach home where it is obvious that the owners care about their rental property. Decorated in beachy vibe, lots of bathrooms, super...
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Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it...
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Beach Bellini is a 3 bedroom/3 bathroom private home in Holmes Beach. Just an 8 minute walk to the beach, pull into the paver driveway with a one-car garage and enter this light and airy home with wood floors and wood plank ceilings. The fully-stocked kitchen has stainless steel appliances, granite counters,...
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35 Steps to the Beach at Runaway Bay 104 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen...
Featured review
We had a great time on the island. The condo seemed to be completely remodeled. It was comfortable and convenient to the beach, grocery store and restaurants. We like the bottom floor and ready access...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS!Welcome to your home-away-from-home! This 4-bedroom, 4 full bath, 2 half bath pet-friendly, canal-front retreat is made for making memories — whether you're here with family, friends, or your fishing crew. From sunrise to sunset, the views,...
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Just a 2 minute walk across the street to the beautiful beaches of Anna Maria Island. This updated coastal beach condo is all you need for a stay in paradise, so slow down and enjoy the Beach life at 3 on Avenue Sea. Bradenton beach is centrally located just south of Anna Maria and Holmes Beach, just...
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Recently renovated and beautifully updated, My Way is a stunning 2-bedroom, 2-bathroom condo located just steps from the soft sands and sparkling waters of Bradenton Beach. Perfectly positioned right across the street from the beach, this stylish retreat combines comfort, convenience, and coastal charm....
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VRC19-000071 Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful Anna Maria Island. This 2-bedroom, 2-bathroom condominium offers all the charm and comforts you will come to expect from a Salty Mermaid Vacation Rental....
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Bougie Bay, a beautiful renovated ground-floor condo located in the sought-after Runaway Bay community. This unit is just steps across the street from the breathtaking Gulf beaches of Anna Maria Island. This bright and stylish 2-bedroom, 2-bathroom unit has been completely updated with modern furnishings,...
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5608 GULF DR UNIT 111 SUN PLAZA WEST, HOLMES BEACH, FL 34217 VRC19-000241 Book with confidence: NO CANCELATION FEES Cancellation Policy $500 deposit due at time of booking; balance due 60 days prior to arrival For reservations 21+ nights or $20,000+ → 10% deposit due at time of booking. Cancel...
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