Anna Maria Rentals
From $1751 per night (USD)VRBO
Newly renovated one-story home with all the amenities and within walking distance to shopping, restaurants and beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Look. No Further! Located in the heart of Anna Maria, this four bedroom, four bath, canal front, single-story renovated ...
From $1751 per night (USD)VRBO
From $969 per night (USD)VRBO
Large Heated Pool, 2 Master Bedroom Suites, Very Close to Gulf Beach.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
'South Cay' is an absolutely beautiful house in "Anna Maria", on Anna Maria Island, Florida. How close to the beach? Th ...
From $969 per night (USD)VRBO
From $1005 per night (USD)VRBO
MAY SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The home has a private be ...
From $1005 per night (USD)VRBO
From $848 per night (USD)VRBO
North end canal front home ,tiki hut, dock, pool, spa, beaches....
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. Thi ...
From $848 per night (USD)VRBO
From $593 per night (USD)VRBO
Waterfront POOL home just Steps to Pine Ave and Beaches in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Anna Maria Beach Vacations brings you this fabulous private pool home in Anna Maria Florida. It boasts, 2 Bedroom and 2 ...
From $593 per night (USD)VRBO
From $386 per night (USD)VRBO
Everything inside is new and beachy! Two blocks to Bean Point Beach!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Our vacation home is two blocks to either the Gulf of Mexico or Tampa Bay…Bean Point Beach! We have remodeled the entire ...
From $386 per night (USD)VRBO
From $427 per night (USD)VRBO
4.9 rated Island rental with exceptional testimonials for over 10 years!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Our highly rated vacation rental home is private, immaculately clean, whimsically decorated, professionally landscaped, ...
From $427 per night (USD)VRBO
From $182 per night (USD)VRBO
Best Location on Island - Read Our Guest Reviews!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Seaside Views - Waterfront, Steps from Beach & Restaurants Best Location on Island - Read Our Guest Reviews! This wate ...
From $182 per night (USD)VRBO
From $1180 per night (USD)VRBO
Spectacular Beachfront House with Pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to 'Sky way view', one of the most exclusive homes on Anna Maria Island. It is located in one of the most specta ...
From $1180 per night (USD)VRBO
From $984 per night (USD)Expedia
Jungalow Bay by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian para ...
From $984 per night (USD)Expedia
From $6292 per night (USD)VRBO
The Rod and Reel Resort
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the new and luxurious Rod and Reel Resort. We are pleased to offer our guests the finest and most inclusive e ...
From $6292 per night (USD)VRBO
From $525 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $525 per night (USD)Expedia
From $809 per night (USD)VRBO
Charming Bungalow with Fabulous Location and Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
***Our home, like so many others on the island, was affected by hurricanes Helene and Milton. It is currently undergoing ...
From $809 per night (USD)VRBO
From $304 per night (USD)Expedia
\"La Casita\" Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in beautiful tropical landscaping, this 2 bed, 2 bath beach cottage vacation rental blends simple elegance with ...
From $304 per night (USD)Expedia
From $500 per night (USD)VRBO
Anna Maria Island Rentals - Beach Front - \"Angels Envy\" -Rod & Reel Pier Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
First, Anna Maria Island is broken up into 3 cities, Anna Maria, Holmes Beach and Bradenton Beach. The City of Anna Mar ...
From $500 per night (USD)VRBO
From $544 per night (USD)VRBO
Private Pool - Seaglass Cottage by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located just a few sandy steps from the turquoise Gulf of Mexico, Seaglass Cottage is the Anna Maria Island beach house ...
From $544 per night (USD)VRBO
From $524 per night (USD)VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING , UNIT B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location! The home located on the very desirable quiet north end of Anna Maria, Florida . This charm ...
From $524 per night (USD)VRBO
From $830 per night (USD)Expedia
Modern Beach House with excellent location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Direct Beach Access, fully renovated beach house. Main floor master suite that walks out to large outdoor living space. ...
From $830 per night (USD)Expedia
Click For PricingVRBO
Anna Maria Northshore beauty W\/ Private Pool. 1 block from Anna Maria Beach!!!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
Enjoy The Good Life! In our unforgettable Beach Home. The property was built to standards for guests who demand the very ...
Click For PricingVRBO
From $544 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING - UNIT A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, Location, Location! The home located on the very desirable quiet north end of Anna Maria, Florida . This charm ...
From $544 per night (USD)Expedia
From $1674 per night (USD)VRBO
Winter Discounts! Steps from the Beach! Walk to Bean Point! Pool\/spa! Golf Cart
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, l ...
From $1674 per night (USD)VRBO
From $202 per night (USD)Expedia
Best location on the island. Private dock, steps to Anna Maria Beach and Pier
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
From our private dock you can watch the sunset, drop a fishing line, watch manatees, or launch your paddle board or kaya ...
From $202 per night (USD)Expedia
From $576 per night (USD)VRBO
Bean Point Beach Cottage - Same street as Rod & Reel Pier & beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
(NEW LISTING!) Vacation at Anna Maria Island with the most beautiful white sands beach and emerald green waters in the w ...
From $576 per night (USD)VRBO
From $2337 per night (USD)Expedia
BEACH NEST IS GETTING A RENOVATION! WE WILL BE BACK! CHECK BACK FOR UPDATES! XOX
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Ahhhh-welcome to Beach Nest! We offer free bikes, 2 tandem kayaks, a beach cart, bubbling hot tub, fishing dock plus a h ...
From $2337 per night (USD)Expedia
From $1368 per night (USD)VRBO
Casa Amiga managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
144 Crescent Dr. Anna Maria, FL 34216 You may cancel your reservation up to 60 days before check-in for a full refund mi ...
From $1368 per night (USD)VRBO
From $1545 per night (USD)Expedia
A Shore Thing - Luxury Waterfront Oasis w\/ Pool, Spa, Rooftop Deck & Dock, Near Bean Point
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to A Shore Thing! On Anna Maria Island (Anna Maria, FL) Experience the ultimate island getaway in this waterfro ...
From $1545 per night (USD)Expedia
From $651 per night (USD)VRBO
LOCATION! -Bean Point area w\/pool. PANORAMIC WATER VIEW. Walk to Beach and town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This is our much-loved AMI family home and we want you to have a wonderful visit. PLEASE be sensitive to the fact (and ...
From $651 per night (USD)VRBO
From $1062 per night (USD)Expedia
Yellowfin Inn: Luxury canal-front, pool home on Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Yellowfin Inn. Our new home away from home. This new construction offers an open floor plan and an awesom ...
From $1062 per night (USD)Expedia
From $634 per night (USD)VRBO
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Naut 2 Shabby Cottage! This 1922 Old-Florida-style cottage pool home is the front unit on the property, locat ...
From $634 per night (USD)VRBO
From $806 per night (USD)Expedia
Bay Bungalow by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly situated in the North end of the island, Bay Bungalow is just a short stroll away from the Bay beaches, and fa ...
From $806 per night (USD)Expedia
From $1686 per night (USD)VRBO
Dragonfly - Southern charm on the North end of Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Dragonfly is a private retreat located right across the street from the sugary white sands of famous Bean Point Beach in ...
From $1686 per night (USD)VRBO
From $701 per night (USD)Expedia
Sunset Shores: Stunning sunset views over the beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Dreaming of the perfect beach vacation home? Dreaming of sipping coffee on your choice of decks with views of the Gulf? ...
From $701 per night (USD)Expedia
Click For PricingVRBO
The Oasis at AMI: Walk to beach, heated pool, hot tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Oasis at AMI! This charming 4 Bedroom 3.5 Bath home is the perfect place to escape it all! With no busy s ...
Click For PricingVRBO
From $997 per night (USD)Expedia
Hook Wine & Sinker by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Hook Wine and Sinker, a gorgeous 2000 square foot canal-front home situated in the coveted North end of Anna ...
From $997 per night (USD)Expedia
From $947 per night (USD)VRBO
Anna Maria Island Private Waterfront Oasis on Bimini Bay | IG: AMIBlueHeron
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Imagine your own private oasis overlooking Bimini Bay on a quiet street on Anna Maria Island. Well, imagine no further. ...
From $947 per night (USD)VRBO
From $493 per night (USD)Expedia
Canal Front - Going Coastal by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground level canal fron ...
From $493 per night (USD)Expedia
From $1534 per night (USD)VRBO
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
As seen in Coastal Living Magazine, this is a quintessential, beachfront home on desirable Bean Point with with direct a ...
From $1534 per night (USD)VRBO
From $837 per night (USD)VRBO
Tucked Away in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked Away is a newly renovated custom home with everything you could possibly need for the vacation of a life time. Th ...
From $837 per night (USD)VRBO
From $1329 per night (USD)VRBO
Bateman's - Luxury 4BR Canal-Front Home w\/ Heated Pool, Spa & Dock
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bateman's! On Anna Maria Island (Anna Maria, FL) Discover the ultimate in coastal luxury at Bateman's, a stu ...
From $1329 per night (USD)VRBO
From $451 per night (USD)Expedia
Dog-friendly house w\/ beautiful upstairs deck and grill, steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sandy's Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $451 per night (USD)Expedia
From $487 per night (USD)VRBO
Anna Maria North End Retreat, Private Pool, 250 feet from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The North Shore House is a clean and peaceful cottage, located in the desirable north end of Anna Maria Island, just 250 ...
From $487 per night (USD)VRBO
From $1439 per night (USD)Expedia
Vitamin Sea managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
146 Crescent Dr, Anna Maria FL 34216 VITAMIN SEA is a home that features 5 bedrooms and 5 bathrooms and a fantastic loca ...
From $1439 per night (USD)Expedia
From $966 per night (USD)VRBO
Dog-friendly house w\/ private heated pool & entertainment - walk to the beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Au Soleil Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $966 per night (USD)VRBO
From $848 per night (USD)Expedia
Pete's Blue Heaven: Steps to beach w\/heated pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Plan your next island vacation at this exception 4 bedroom, 2 bath home located at the north end of Anna Maria! Enjoy th ...
From $848 per night (USD)Expedia
From $1012 per night (USD)VRBO
Black Pearl: 4 BR, 3 BA House in Anna Maria, Sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
With 4 bedrooms and 3 full bathrooms, Black Pearl, with it's art deco décor has as much space as it does charm. In addit ...
From $1012 per night (USD)VRBO
From $436 per night (USD)Expedia
Canary Cottage Perfect modern cottage, quiet street, short walk to the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Canary Cottage has 2 bedrooms and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- Thi ...
From $436 per night (USD)Expedia
From $287 per night (USD)VRBO
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna Maria, West of Gulf Drive and o ...
From $287 per night (USD)VRBO
From $190 per night (USD)Expedia
☀️🌊🐟❤️Love Shack on the Water (Most Desirable Location on AMI)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Located on Pine Ave just steps from shops, the General Store, restaurants, the pier, beach, pier fishing, and the trolle ...
From $190 per night (USD)Expedia
From $1536 per night (USD)VRBO
Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool\/Spa |
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bimini Bay Breeze is a gorgeous canal front home with an expansive outdoor living area and is conveniently located close ...
From $1536 per night (USD)VRBO
From $492 per night (USD)Expedia
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CAST AWAY your stress and worries at this adorable piece of old Florida near BEAN POINT. Charming vintage cottage with L ...
From $492 per night (USD)Expedia
From $565 per night (USD)VRBO
Steps to Beach Access, Bean Point\n3-4 Bdr Mother-in-law Site Option Downstairs\n
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Coco-Nut's of Anna Maria Island is the upstairs of a beautiful 3 bedroom, 2 bath home steps from the pristine white sand ...
From $565 per night (USD)VRBO
From $732 per night (USD)VRBO
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach chic meets casual elegance in this brand new ground level cottage only steps away from the best beach on Anna Mari ...
From $732 per night (USD)VRBO
From $1859 per night (USD)VRBO
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" *Construc ...
From $1859 per night (USD)VRBO
From $694 per night (USD)Expedia
Bliss by the Beach by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy beachside bliss in this luxury home on the secluded and desirable North end of Anna Maria near Bean Point! *Featu ...
From $694 per night (USD)Expedia
From $669 per night (USD)VRBO
Anna Marie Hideaway!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
2013 is the first year we have rented our family beach house on Anna Maria Island. Our kids are in school and it is hard ...
From $669 per night (USD)VRBO
From $1979 per night (USD)Expedia
Felicity: Luxury Bayfront Home, Heated Pool, Hot tub and more!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Beachfront Felicity in Anna Maria Welcome to Felicity (formerly known as Bay Breeze)! This is one of the most exclusive ...
From $1979 per night (USD)Expedia
From $815 per night (USD)VRBO
Tides Inn- Family home with tropical pool area.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself to the relaxing getaway your family has been daydreaming about! The Tide’s Inn is a pet friendly vacation ...
From $815 per night (USD)VRBO
From $568 per night (USD)Expedia
Sorgenfrei South: Charming beach getaway across from the Gulf!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Sorgenfrei South has everything you need for a perfect beach getaway. This stunning 3 bedroom, 3.5 bath home is located ...
From $568 per night (USD)Expedia
From $658 per night (USD)VRBO
Private Salt Water Pool & Spa, WALK TO BEACH, near Bean Point, GROUND LEVEL.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This family friendly beach house features cool tile floors, a 60" flat screen TV, complimentary WiFi and YouTubeTV and ...
From $658 per night (USD)VRBO
From $570 per night (USD)Expedia
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Calienta🐬
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Renovated. 🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl T ...
From $570 per night (USD)Expedia
From $2300 per night (USD)VRBO
Spoil yourselves! Gulf front, heated pool & hot tub. NO DAMAGE! GUESTS WELCOME!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
ANNA MARIA IS OPEN: OUR BEACHES, SHOPS AND RESTAURANTS. JOIN OUR GUESTS DRIVING GOLF CARTS, COLLECTING SHELLS AND RIDING ...
From $2300 per night (USD)VRBO
From $524 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $524 per night (USD)Expedia
From $482 per night (USD)VRBO
Cozy Cottage w private Beach Access, AC&WiFi - NorthEnd AMI. No hurricane damage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
No hurricane damages! We have replanted the damaged landscape and fence. Sea Garden Cottage is a true island gem and e ...
From $482 per night (USD)VRBO
From $986 per night (USD)Expedia
Jacaranda Gem by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Take a break from the hustle and bustle, and relax in the calm and serene atmosphere of this spotless vacation home. Jac ...
From $986 per night (USD)Expedia
From $1208 per night (USD)VRBO
North End AMI, Pool,Ocean Views,Tropical Oasis and elevator. No hurricane Damage
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
No hurricane damages to the house. This home is a showcase stunner! Sea Breeze was has been remodeled and professional ...
From $1208 per night (USD)VRBO
From $567 per night (USD)Expedia
Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in ...
From $567 per night (USD)Expedia
From $374 per night (USD)VRBO
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We only rent thru VRBO! Your safety is our priority. We are writing here as the owners of this lovely cottage. If you ...
From $374 per night (USD)VRBO
From $1453 per night (USD)VRBO
Stunning new 4 bedroom 4.5 bath home with heated pool\/spa and views of Tampa Bay
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
THANK YOU TO ALL OUR PAST, FUTURE AND POTENTIAL GUESTS WHO HAVE REACHED OUT TO US IN THE LAST FEW WEEKS TO INQUIRE ABOUT ...
From $1453 per night (USD)VRBO
From $444 per night (USD)VRBO
Northshore Beach House near Pine Ave, north end of Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pine Ave and Northshore Drive adorable beach home. Fully restored and remodeled post Hurricane Helene. We are open for g ...
From $444 per night (USD)VRBO
From $999 per night (USD)VRBO
Hear The Surf\/Feel The Breeze... skip to beach!\nLocated on Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Just 5 houses from the white sandy beach of the Gulf. Located in the city of Anna Maria sits this spacious home with ...
From $999 per night (USD)VRBO
From $450 per night (USD)VRBO
Turtle Cottage - Anna Maria Island
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Great 1 bedroom, 1 bathroom cottage on the quiet north end of island. The house is conveniently located and within walki ...
From $450 per night (USD)VRBO
From $1790 per night (USD)Expedia
Reef Romance managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, fou ...
From $1790 per night (USD)Expedia
From $481 per night (USD)VRBO
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Barefoot Gypsy is an enchanted cottage tucked in the north end of Anna Maria Island in the City of Anna Maria, .Flor ...
From $481 per night (USD)VRBO
From $935 per night (USD)VRBO
The Happy Hibiscus Island Oasis with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to The Happy Hibiscus! We are located in a perfect location where we can catch the sunrise and sunset, less than ...
From $935 per night (USD)VRBO
From $522 per night (USD)VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - UPPER UNIT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $522 per night (USD)VRBO
From $463 per night (USD)VRBO
Perfect Anna Maria-20% off Aug\/Sep\n 3 blocks to sugar sand beach. Heated pool.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
3 short blocks to the sugar sand beaches of the Gulf of Mexico and 5 blocks to Tampa Bay. This traditional Florida home ...
From $463 per night (USD)VRBO
From $320 per night (USD)VRBO
Blue Heron Cottage - Anna Maria Island
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 4
Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within wal ...
From $320 per night (USD)VRBO
From $968 per night (USD)VRBO
May Deal! - Canal \/Hot Tub\/Htd Pool\/ Dock\/Backyard Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Last Minute Deal May 3 - 10, 2025 now $2,799* plus fees & taxes Sirenia Cove is ready to receive you. Pool is heated an ...
From $968 per night (USD)VRBO
From $242 per night (USD)VRBO
Bungalow On The Bayou (Best Location on the Island)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a specta ...
From $242 per night (USD)VRBO
From $710 per night (USD)VRBO
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite ...
From $710 per night (USD)VRBO
From $723 per night (USD)VRBO
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Sea Waves, our newly renovated home with 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natur ...
From $723 per night (USD)VRBO
From $440 per night (USD)Expedia
Spacious beach house with a beautiful view of the gulf
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The fully air-conditioned house is in a quiet, exclusive residential area at the tip of the island. Miles of white sandy ...
From $440 per night (USD)Expedia
From $1232 per night (USD)VRBO
CabAnna Maria Beach Block 4 Bedroom 4.5 Bath
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
CabAnna Maria is a newly renovated 4 bedroom, 4.5 bath house, that sleeps 8 (max) comfortably, a quick 450 ft to the pri ...
From $1232 per night (USD)VRBO
From $1130 per night (USD)VRBO
April Deals! - Waterfront\/HotTub\/ Pool\/Dock\/PuttGreen\/Backyard Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Last Minute Deals April 19 - 26, 2025 now $3,999* plus fees & taxes April 26 - May 3, 2025 now $2,999* plus fees & taxes ...
From $1130 per night (USD)VRBO
From $929 per night (USD)VRBO
Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK <br>
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This large home was constructed in 2009. It is a decorator furnished, pool home and considered top of the line in vacat ...
From $929 per night (USD)VRBO
From $260 per night (USD)Expedia
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Ballyhoo is a ground floor cottage located on Bean Point at the very tip of Anna Maria Island. Around the corner, (2 ...
From $260 per night (USD)Expedia
From $233 per night (USD)VRBO
Adorable Cottage ONLY STEPS to Anna Maria Beach, No Roads to Cross! FREE WiFi...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
**ASK ABOUT LAST MINUTE DEALS! Enjoy a simple, old fashioned seaside vacation in this adorable duplex west ...
From $233 per night (USD)VRBO
From $282 per night (USD)Expedia
FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to Cross!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
**ASK ABOUT LAST MINUTE DEALS! Island fun is easy in this 2 unit charming cottage located two houses from t ...
From $282 per night (USD)Expedia
From $449 per night (USD)VRBO
4 Bed\/2.5 Bath Duplex, FREE WiFi & Trolley, ONLY STEPS to Pristine Sandy...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a simple, old-fashioned seaside vacation in this adorable duplex west ...
From $449 per night (USD)VRBO
From $712 per night (USD)Expedia
Gladiolus on the Water by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation get ...
From $712 per night (USD)Expedia
From $824 per night (USD)VRBO
Welcome to Acquaviva!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Acquaviva by Anna Maria Island Accommodations Canal front home in Anna Maria, Florida Welcome to Acquaviva, a spectacul ...
From $824 per night (USD)VRBO
From $1335 per night (USD)Expedia
Waves- steps from the beach with a water view
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Waves - Your Perfect Anna Maria Island Getaway! Experience the ultimate beach retreat at Waves, a luxurious ...
From $1335 per night (USD)Expedia
Click For PricingVRBO
Welcome to The Beach House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Beach House by Anna Maria Vacations 9308 Gulf Drive Anna Maria, Fl. 34216 VR16-000455 This modern 3 bedroom 2.5 ba ...
Click For PricingVRBO
From $1756 per night (USD)Expedia
Rooftop Deck, Private Pool and Game room! Perfect for Families!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 8
Boundless Waves by Anna Maria Island Accommodations Anna Maria, Florida Welcome to Boundless Waves, an incredible vac ...
From $1756 per night (USD)Expedia
From $939 per night (USD)VRBO
Bimini Bay: 3 Blocks to Beach! Private Pool! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Bimini Bay by Anna Maria Life Vacation Rentals 312 Hardin Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $939 per night (USD)VRBO
From $720 per night (USD)Expedia
The Poop Deck: *Pet-friendly *Canalfront *Heated Pool *Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Escape to The Poop Deck, an enchanting 4-bedroom, 3.5-bathroom A-frame haven on Anna Maria Island. Its charming design a ...
From $720 per night (USD)Expedia
From $1143 per night (USD)VRBO
West O' Gulf, amazing location, steps to beach and fun on AMI
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to West O' Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than eve ...
From $1143 per night (USD)VRBO
From $887 per night (USD)Expedia
Canal Place: Boat Dock, Pool & Spa, On Canal by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
238 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! 2 Blocks to Gulf Beach! On a Canal! 3 ...
From $887 per night (USD)Expedia
From $788 per night (USD)VRBO
Idyll Tides by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the ultimate island retreat you've been dreaming of ~ Idyll Tides ~ a stunning vacation home nestled on the nor ...
From $788 per night (USD)VRBO
From $1003 per night (USD)Expedia
Canal-Front Oasis with Private Dock, Pool, Near Beach & Shops - Aqua Cove
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Aqua Cove by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000429 Welcome to Aqua Cove, a dream retreat for fa ...
From $1003 per night (USD)Expedia