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Distance to beach: 45 feet to Gulf of Mexico
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Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead and you are on North Bay Boulevard Beach. Walk 4 more lots to the left and you are on Bean Point! Or walk 5 lots further left and you are on the Gulf of Mexico. Perfectly situated next...
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Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
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Welcome to Mermaid Manor — a tranquil retreat on beautiful Anna Maria Island. This inviting duplex home is the ideal spot for couples, families, or friends looking to enjoy the island’s sun-soaked charm and relaxed pace.Each level of the duplex are full floor units (lower and upper level...
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This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...
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Turtle's Bay by Beach Retreats Vacation Rentals 306 Clark Dr Unit B, Holmes Beach, Anna Maria Island VRC17-000006 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsDog...
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 Hidden Treasure Unit B! VRC25-000106 .1 Miles to Holmes Beach Shared Heated Pool Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals High-speed Wi-Fi included Smart lock for Self Check-in...
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306 67th Street Unit B Holmes Beach, FL 34217 VRC Caribbean Surf by Beach Retreats Vacation RentalsHolmes Beach, Anna Maria Island 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-FriendlyYour Anna Maria Island Bungalow Retreat Welcome to Caribbean Surf, a bright and inviting...
Featured review
The home has recently been redone, very comfortable and accomodating with a nice sitting deck and new pool. We had a short walk to a beach access and the location allowed us to visit the north island area...
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My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the...
Featured review
Very comfortable cottage. Close to Walgreens, Publix, and small shopping stores. Beds were comfortable and really enjoyed the step down sun room. Back porch was great for watching sunsets. Very short distance...
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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...
Distance to beach: 0.1 miles to 30 seconds to your left
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This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and...
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Crosswind Cottage 312 A 61st Street, Holmes Beach, FL 34217 VRC19-000277 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighborsWelcome to Crosswind Cottage, a spacious island retreat...
Distance to beach: 0.1 miles to Bayside Beach
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Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms and 3 Bathrooms...
Featured review
Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...
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Vitamin Sea by Beach Retreats Vacation Rentals 146 Crescent Dr, Anna Maria, FL 34216Welcome to Vitamin Sea, a stunning 5-bedroom, 5-bath luxury retreat located on the coveted north end of Anna Maria Island, just a 10-minute stroll to Bean Point Beach. With a private dock, heated saltwater pool and...
Featured review
Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming,...
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This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and...
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I try to work with your budget!- please inquire!!! If our cottage is booked, I help people with other cottages- you will love it!Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find...
Featured review
Location, location! Perfect for daily visits to the beach and surrounding areas. The resort was clean, and the staff went above and beyond to ensure our vacation was perfect!
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One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...
Featured review
We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...
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Welcome to Mermaid Sunset! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Pool Heat included with rental Welcome to Mermaid...
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Discover Your Perfect Beach Retreat at Bimini Breeze!Pack your bags (and some sunscreen) because you’re about to dive into an unforgettable getaway at Bimini Breeze! This stunning elevated home is just steps away from the pristine beaches of Anna Maria Island. With four bedrooms and three and...
Featured review
What a great home to visit on your Anna Maria Island vacation! Everything was exceptional and we made tons of great family memories together here. Highly recommend!
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This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...
Featured review
We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It...
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Welcome to Mermaid Sunrise! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in *Pool heat is unavailable as of 4/7/2026 and will...
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Steps to Beach + Heated Pool + Putting Green + Golf Cart | WavesWelcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape.Perfectly positioned just across...
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Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...
Featured review
The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally...
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Just Beachy – Your Luxury Island Retreat on Anna Maria Island 128 49th Street Holmes Beach FL 34217 VRC21-000019 4 Bedrooms + nanny suite | 6 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub | This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighborsEscape...
Featured review
We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its...
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Welcome to Hidden Treasure Unit A! VRC18-000124.1 Miles to Holmes Beach Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals Shared Heated Pool High-speed Wi-Fi included Smart lock for Self Check-in...
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Welcome to Sailfish Nest, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax in...
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Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect...
Featured review
Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....
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This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...
Featured review
Loved this rental. Close to beach and has a pool. Pet friendly too. Roomy and well stocked with kitchen items as well as towels.
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Please reach out for a quote or if you have any questions, we respond quickly. Welcome to Sol Y Mar! This bright, newly refreshed 3 Bedroom beach house oasis features the perfect mix of modern decor mixed with touches of mid-century inspired furnishings and original terrazzo floors. Guest will love the...
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VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:“You are vacationing in...
Featured review
We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days...
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This charming unit with a PRIVATE entrance is part of a cozy three-unit complex, sharing only the pool and grill, with pool-front views and easy-access parking. This spring, enjoy blooming island beauty and warm coastal breezes just steps from sparkling beaches, local restaurants, and unique boutiques,...
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Salt + Sol | Canal-Front Oasis + NEW Heated Pool + Golf Cart | North End RetreatWelcome to Salt + Sol, your serene canal-front escape on the coveted north end of Anna Maria Island. This bright and breezy 4-bedroom home blends relaxed coastal elegance with modern comfort — all just minutes from...
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KEY FEATURES:Everything You Need for a Perfect Beach Day Chairs, toys, cooler, wagon, umbrella—you’re covered! Just bring your swimsuit.3 Plush Bedrooms with Smart TVs King, queen, and a twin-over-full bunk room—all with luxe mattresses and streaming-ready TVs.Just a...
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Welcome spring at the Suites, where sunshine, blooming flowers, and coastal breezes set the tone for a perfect getaway. Just steps from the beach, enjoy morning coffee or evening sunsets on the spacious screened porch. Stroll to shops, dining, and island attractions, or hop on the free ferry to explore...
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Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...
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Retreat this spring to the warmth and laid-back charm of Anna Maria Island, where blooms and gentle breezes fill the air. This unit features a PRIVATE entrance in a cozy three-unit complex, sharing only the heated pool and grill area. Just steps from sandy beaches, enjoy sunsets, dining, and shops. Hop...
Featured review
We loved the location and it was perfect for just the two of us and our dog. A quick walk to the beach What more can you want.
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Steps to Beach + Heated Pool + Golf Cart & Bikes | North End RetreatThis beautifully remodeled 4-bedroom, 4-bath Anna Maria Island vacation home is perfectly situated on the coveted north end — just steps from the Gulf of Mexico. With a convenient beach access path directly across the street,...
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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 This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Completely Renovated February 2025! Welcome to Conch-Out Beach...
Featured review
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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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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Sandcastle – Beachside Escape with Heated Pool, Golf Cart & Island Adventure Gear3 Bedrooms | 2.5 Bathrooms | Heated Pool | Golf Cart | Bikes | Paddle Boards | Kayaks | Steps to the BeachWelcome to Sandcastle, your perfect Anna Maria Island beach retreat. Ideally located just across...
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When it's time to run away— to escape to a tropical island oasis where the bright sun is shining and the gentle sea breezes are endless— then it's time to book a stay at Runaway Bay 117. This cozy coastal hideaway is tucked within one of the most exclusive Anna Maria Island communities...
Featured review
We've been on Ana Maria Island before; it's a lovely area. This was a great location for us and the management was very prompt and considerate whenever we contacted them. Thank you so much!
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In the heart of Holmes Beach on Anna Maria Island rests this charming recently renovated, pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior creates a welcoming and calming environment....
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to Beachy Keen, your dream getaway on beautiful Anna Maria Island! This bright and spacious 5-bedroom, 4-bathroom home comfortably sleeps up to 12 guests and offers everything you need for a relaxing and memorable beach vacation.Step inside...
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Starfish Isle by Beach Retreats Vacation Rentals 5803 Holmes Blvd Holmes Beach, FL 34217 VRC 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighborsAt 4 bedrooms and 3 full bathrooms,...
Featured review
The home was absolutely wonderful with everything we needed to make our weeklong vacation a success! Everything was clean and well kept. The beds were comfortable and the best part was the pool and pool...
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Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk...
Featured review
Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first...
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Welcome to your island retreat in the heart of Holmes Beach, Florida. This pet-friendly property offers a light-filled, thoughtfully laid-out interior that blends coastal charm with everyday comfort, perfect for your vacation getaway.The main living space features an open-concept design with warm...
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Kickback Cabana 411 79th Street Holmes Beach FL 34217 VRC19-000189 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool & Hot Tub | Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation fees! Cancel 60+ days before arrival →...
Featured review
We really enjoyed this vacation rental home. Excellent location with close proximity to the beach and restaurants. Also, house located on a quiet street. Amenities were great including the pool and the...
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35 Steps to the Sea at Runaway Bay 112 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
This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people....
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Emerald Bay Beach House 306A Clark Street, Holmes Beach, FL 34217 VRC17-000006 | 3 Bedrooms Plus Bonus Bunk Room | 3.5 Bathrooms | Sleeps 6 | Heated Pool & Spa Welcome to Emerald Bay Beach House, your ultimate escape on Anna Maria Island! Our dreamy amenities ensure that guests enjoy a perfect...
Featured review
This was our perfect getaway. The house is beautifully decorated inspired by the blue glistening water and white sandy beaches of Ana Maria Island. The kitchen was fully equipped with everything we needed...
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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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Welcome to Stillpoint, a beautifully designed single-level home just one block from the beach in the heart of Holmes Beach, where island ease meets modern comfort. Thoughtfully laid out and ideal for families or multiple guests, this 3-bedroom, 2-bath getaway is pet-friendly (1 dog allowed) and perfectly...
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