5 BR | 5 BA | Sleeps 14 | Quick View
Distance to beach: 0.1 miles to Bayside Beach
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About this property
Just updated 2020, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...
Property Type
Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
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About this property
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 ...
Property Type
Anna Maria Island House
What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...
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About this property
Come experience Unit 204 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 pool and ...
Property Type
Anna Maria Island Condo
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About this property
Condo-cottage with Old Florida charm..... 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 quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...
Property Type
Anna Maria Island Cottage
We gave this 5 stars but my husband wanted to do 4 1/2. The reason he was disappointed that the dock and pier are set up for fishing, but the staff knew nothing about it. Also, seems like it would be smart ...
6 BR | 5.5 BA | Sleeps 14 | Quick View
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About this property
ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...
Property Type
Anna Maria Island House
Beach house was so nice, clean and beautiful. We had plenty of room for our party of eleven. Very short walk to the beach. Loved the pool area. Would stay at Oceanview again. Weldon checked on us and made ...
5 BR | 2 BA | Sleeps 10 | Quick View
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About this property
One of the highest rated vacation homes on Anna Maria Island with more than 150 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 ...
Property Type
Anna Maria Island House
We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...
3 BR | 3 BA | Sleeps 6 | Quick View
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About this property
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 ...
Property Type
Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Distance to beach: 0.1 miles to 30 seconds to your left
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About this property
This newly redesigned elevated 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 it's stunningly ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Relax with the whole family at this peaceful place to stay.Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach.We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs!Endless ...
Property Type
Anna Maria Island Condo
My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...
5 BR | 4.5 BA | Sleeps 10 | Quick View
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About this property
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 ...
Property Type
Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
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About this property
Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...
Property Type
Anna Maria Island House
Key Amenities
About this property
To Book Directly please visit: /its-miller-time If 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: This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen ...
Property Type
Anna Maria Island House
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About this property
*** SPECIAL *** Book a 14 day stay and ONLY pay for 12Buckeye Haven s situated in one of the sought after community of Playa Encantada! Come enjoy this tropical beach front community on the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as ...
Property Type
Anna Maria Island Condo
Key Amenities
About this property
Pine Avenue HideAway is a secluded Beach Bungalow tucked away on Historic Pine Avenue on Anna Maria's North End. Conveniently located in the heart of it all, and just a short stroll to the beach, restaurants, boutiques, Anna Maria City Pier and a trolley stop to explore Anna Maria the islanders way!. ...
Property Type
Anna Maria Island Bungalow
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
North End Escape is a 2,300 sq. ft. Newly Built 3 bedroom 2 ½ bathroom Custom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool.This spacious home has wide plank hardwood flooring throughout; open concept ...
Property Type
Anna Maria Island House
Key Amenities
About this property
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 ...
Property Type
Anna Maria Island Cottage
So close to the water for someone with gait issues. We always enjoy our stay here. So close to restaurants and beach. Best of both worlds
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to the Rod and Reel Pier, Bay Front Park and the popular white sandy beach of Bean ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Welcome to SURF’S UP! Located one block from the sugary white sand beaches on the desirable north end of the Anna Maria. SURF’S UP is a 2 bedroom, 2 bath cottage that has been completely and lovingly renovated from top to bottom and is gorgeously decorated, meticulously maintained and ready ...
Property Type
Anna Maria Island Cottage
2 BR | 2 BA | Sleeps 4 | Quick View
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About this property
Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach.Inside it has a split plan with a king sized bedroom and a second bedroom ...
Property Type
Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceWe are proud to feature this gorgeous, custom-built, professionally designed, ...
Property Type
Anna Maria Island House
Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.
4 BR | 3.5 BA | Sleeps 8 | Quick View
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About this property
Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a den where the kids can hang out with a TV and sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island vacation! ...
Property Type
Anna Maria Island House
This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk to the beach ...
4 BR | 3 BA | Sleeps 8 | Quick View
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About this property
210 65th Street Holmes Beach, FL 34216 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island Bungalow
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 ...
Key Amenities
About this property
Large 4 bedroom/2 bathroom Ocean view home with screened porches in the front and back. Elevator to the main level. Beach is right across the street. Bikes, Paddle Boards and a golf cart included. We are pet friendly! Pre-approved pet's , a signed pet agreement and pet fee paid in full will be needed. ...
Property Type
Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
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About this property
Manatee Lookout is a charming 3 bedroom/3 bath home with 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 relax ...
Property Type
Anna Maria Island House
We enjoyed our trip to Anna Maria. Very quant, quiet beach. Beautiful clear water and amazing sunsets. Can’t wait to go back!!!
1 BR | 1 BA | Sleeps 4 | Quick View
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About this property
Dans Florida Condos Sea Esta, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...
Property Type
Anna Maria Island Apartment
The location is great, right across street from beach. Trolly stop nearby to ride around the beach and get off at other stops for free. Places to eat within walking distance. Nice pool and tennis courts. ...
5 BR | 3 BA | Sleeps 10 | Quick View
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About this property
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 (around 200 steps) ...
Property Type
Anna Maria Island House
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 ...
6 BR | 6.5 BA | Sleeps 12 | Quick View
Key Amenities
About this property
401 42nd Street Holmes Beach, FL 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island House
We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard ...
4 BR | 3 BA | Sleeps 8 | Quick View
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About this property
VRC 21 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one or two families to stay at. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is ...
Property Type
Anna Maria Island Bungalow
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 ...
Key Amenities
About this property
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 ...
Property Type
Anna Maria Island Condo
Really enjoyed our stay at 35 steps to the beach. Best equipped kitchen for eating in of any condo I’ve stayed in (doesn’t include anything perishable). Clean and comfortable and extremely convenient ...
3 BR | 2.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
411 79th Street Holmes Beach, Fl 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island House
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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About this property
320 64th Street - Holmes Beach - FL - 34217 VRC Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard Oasis BOOK WITH CONFIDENCE Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations ...
Property Type
Anna Maria Island Townhome
Perfect place to stay , no problems at all !! Backyard with heated pool and heated jacuzzi was a perfect place to relax !!
3 BR | 2 BA | Sleeps 6 | Quick View
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About this property
302 60th Street Holmes Beach, FL 34217 VRC At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for your next Anna Maria Island getaway! Two short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish ...
Property Type
Anna Maria Island Townhome
My husband and I had the best time at the home we rented on Anna Maria Island. It was spacious and we had far more room than we needed for just the two of us. When we arrived, everything was clean and easy ...
5 BR | 5 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den North End of Anna Maria Island. Professionally decorated and finished with all King Beds and En-Suite Bathrooms. Chef's Kitchen with a 48inch gas range. Wine Cooler on two levels and a private covered porch to enjoy the sunsets on the upper levels. ...
Property Type
Anna Maria Island House
Key Amenities
About this property
VRC19 5th Ave Holmes Beach, FL 34217 Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total. We do our ...
Property Type
Anna Maria Island House
House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.
4 BR | 3 BA | Sleeps 8 | Quick View
Key Amenities
About this property
202 81 st Street - Holmes Beach - Fl 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...
Property Type
Anna Maria Island Townhome
We enjoyed our stay. The access to the beach and other amenities was perfect for our family. The rental was very clean and well kept. Most everything you needed for the stay was available. The pool was ...
Key Amenities
About this property
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 ...
Property Type
Anna Maria Island Condo
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. ...
4 BR | 4 BA | Sleeps 8 | Quick View
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About this property
Mintfish is a tropical hideaway that blends high-end decor with natural beauty. This 4 bedroom, 4 bath ground-level luxury vacation home has recently been remodeled to combine natural and sustainable materials with decadent living. The single-floor layout makes the home easily accessible to people of ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Dans Florida Condos Sea Dream, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...
Property Type
Anna Maria Island Apartment
This is the first time we stayed at Dans Florida Condos. The condos were right across the street from the private beach access, and I could not have asked for a cleaner unit. Pictures tell the whole story. ...
2 BR | 2 BA | Sleeps 4 | Quick View
Key Amenities
About this property
VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total. 7106 Marina Dr - Holmes ...
Property Type
Anna Maria Island House
Key Amenities
About this property
LimeFish is a luxurious newly remodeled 3 bedroom (1 king-sized, 1 queen-sized, and a bunk room)/3 bathroom single level home right on the sands of Anna Maria Island. Additional sleeping accommodations can be added with the sleeper sofa in the living room. It is a perfect destination for a trip with family ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
In the heart of Holmes Beach on Anna Maria Island rests this charming 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 showcases island artwork, creating a welcoming and calming environment. ...
Property Type
Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
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About this property
Welcome to WAVES, your ultimate beach view retreat located across the street from the Beach. This stunning 4 bedroom home is eagerly awaiting your arrival after undergoing a full remodel ensuring a luxurious and comfortable stay for all guests.As soon as you step inside you'll be greeted by the ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Luxury 2BR/2BA apartment with beautiful oceanfront views. Just steps from the sand, this modern seaside retreat features a fully equipped kitchen and a relaxing patio to watch the beautiful beach sunsets. The area offers dining, a gym, and beach rentals.Aesthetic Grass Wall Cozy Turf Grass Lined ...
Property Type
Anna Maria Island Apartment
Key Amenities
About this property
Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...
Property Type
Anna Maria Island House
5 BR | 3.5 BA | Sleeps 12 | Quick View
Distance to beach: 0.2 miles to bradenton beach
Key Amenities
About this property
You will fall in love with this peaceful retreat. This home comes with (2) 6 person golf cart. You will love zooming around the island on the golf carts, window shopping at all of the gorgeous real estate. This unit is within walking distance to the beach, you will love being able to walk back and forth ...
Property Type
Anna Maria Island House
This house was perfect for us. It had everything we needed and then some. The fact that it’s a duplex worked out great for us too. The pool was used daily, and the backyard was a perfect place for ...
4 BR | 4 BA | Sleeps 8 | Quick View
Key Amenities
About this property
Escape to Your Exclusive Tropical Retreat!Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience, ...
Property Type
Anna Maria Island House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Key Amenities
About this property
306 (A) Clark St - Holmes Beach - FL 34217VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...
Property Type
Anna Maria Island Townhome
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 ...
Key Amenities
About this property
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Located on the North End of Anna Maria Island. Gas BBQ on the lower deck. TV are located in all bedrooms. Plenty of space ...
Property Type
Anna Maria Island House
Key Amenities
About this property
Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you to ...
Property Type
Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Key Amenities
About this property
Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath duplex is located on the north end of desirable Holmes Beach. This home offers all the comforts of home and is just steps to the beautiful white sandy beach. The kitchen is fully equipped ...
Property Type
Anna Maria Island House
Great location in middle of Ana Marie Island; close to beach, not to far to shopping and restaurants.Rum Dog is a clean two bedroom pet friendly unit with wonderful deck for eating and socializingRental ...
