Anna Maria Rentals
From $1311 per night (USD)VRBO
Jungalow Beach by Beach Boutique Rentals
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Jungalow Beach, a modern architectural gem perched close to the beach on Anna Maria’s North End where stunnin ...
From $1311 per night (USD)VRBO
From $469 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 $469 per night (USD)Expedia
From $556 per night (USD)VRBO
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Like so many homes on Anna Maria Island, our home was severely flooded. Professional photos are coming, but until t ...
From $556 per night (USD)VRBO
From $508 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 $508 per night (USD)VRBO
From $249 per night (USD)VRBO
\"La Casita\" Beautiful, Elegant Florida Cottage, 1 Minute Walk to the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in beautiful tropical landscaping, this 2 bed, 2 bath beach cottage vacation rental blends simple elegance with ...
From $249 per night (USD)VRBO
From $407 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 $407 per night (USD)VRBO
From $480 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 $480 per night (USD)VRBO
From $922 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 $922 per night (USD)Expedia
From $883 per night (USD)VRBO
Anna Maria Northshore beauty W/ Private Pool. 1 block from Anna Maria Beach!!!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Enjoy The Good Life! In our unforgettable Beach Home. The property was built to standards for guests who demand the very ...
From $883 per night (USD)VRBO
From $475 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 $475 per night (USD)Expedia
From $211 per night (USD)VRBO
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 $211 per night (USD)VRBO
From $1185 per night (USD)VRBO
Summer 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 $1185 per night (USD)VRBO
From $576 per night (USD)VRBO
Bean Point Beach Cottage -North End of Island beautiful white sand and sunsets!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bean Point Beach. Vacation at Anna Maria Island with the most beautiful white sands beach and crystal clear emerald gree ...
From $576 per night (USD)VRBO
From $2326 per night (USD)Expedia
BEACH NEST IS GETTING A RENOVATION! WE WILL BE BACK! CHECK BACK FOR UPDATES! XOX
- Bedrooms:
- 1
- 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 $2326 per night (USD)Expedia
From $1111 per night (USD)VRBO
Casa Amiga managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $1111 per night (USD)VRBO
From $956 per night (USD)Expedia
A Shore Thing – Waterfront w/ Pool, Spa, Rooftop Deck & Dock Near Bean Point
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
<p>Close to sailing, scuba diving, and more, this smoke-free vacation home brings it all within reach. There's convenien ...
From $956 per night (USD)Expedia
From $642 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 $642 per night (USD)VRBO
From $1157 per night (USD)Expedia
Dragonfly - Southern charm on the North end of Anna Maria Island
- Bedrooms:
- 3
- 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 $1157 per night (USD)Expedia
From $787 per night (USD)VRBO
Yellowfin Inn: Luxury canal-front, pool home on Anna Maria Island
- Bedrooms:
- 4
- 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 $787 per night (USD)VRBO
From $476 per night (USD)Expedia
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely restored with all new kitchen and appliances, new flooring and all new furnishings just as cute! Welcome to ...
From $476 per night (USD)Expedia
From $568 per night (USD)VRBO
Bay Bungalow by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $568 per night (USD)VRBO
From $535 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- 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 $535 per night (USD)Expedia
From $670 per night (USD)VRBO
Hook Wine & Sinker by Beach Boutique Rentals
- Bedrooms:
- 2
- 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 $670 per night (USD)VRBO
From $449 per night (USD)Expedia
Canal Front - Going Coastal by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
NEWLY RENOVATED! Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground ...
From $449 per night (USD)Expedia
From $1220 per night (USD)VRBO
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
- Bedrooms:
- 3
- 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 $1220 per night (USD)VRBO
From $624 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 $624 per night (USD)VRBO
From $1234 per night (USD)VRBO
Batemans - Lux 4BR Canal-Front Home w/ Pool & Dock
- Bedrooms:
- 4
- 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 $1234 per night (USD)VRBO
From $486 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 $486 per night (USD)VRBO
From $957 per night (USD)VRBO
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 $957 per night (USD)VRBO
From $966 per night (USD)Expedia
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)Expedia
From $355 per night (USD)VRBO
Dog-friendly house w/ beautiful upstairs deck and grill, steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sandy's Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $355 per night (USD)VRBO
From $400 per night (USD)VRBO
Charming Beach home sits amongst huge Banyan Trees, walk to beach’s & Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Voted a Tropical paradise perched among native banyon trees. Wake to the sound of sea birds in this tropical paradise. P ...
From $400 per night (USD)VRBO
From $521 per night (USD)VRBO
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 $521 per night (USD)VRBO
From $290 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 $290 per night (USD)Expedia
From $306 per night (USD)VRBO
Sea Spray 2: *Pet-friendly *Steps to the beach *Close to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Photos Updated April 2025*** The Sea Spray Cottages are an adorable group of 4 Units located in the North End of Anna ...
From $306 per night (USD)VRBO
From $1049 per night (USD)Expedia
Bimini Bay Breeze: Canal Front | Close to Beach and Pine St. | Pool/Spa |
- Bedrooms:
- 3
- 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 $1049 per night (USD)Expedia
From $480 per night (USD)VRBO
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
- Bedrooms:
- 1
- 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 $480 per night (USD)VRBO
From $838 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 $838 per night (USD)VRBO
From $1201 per night (USD)VRBO
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" *Construc ...
From $1201 per night (USD)VRBO
From $510 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 $510 per night (USD)Expedia
From $539 per night (USD)VRBO
September Golf Cart Special
- 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 $539 per night (USD)VRBO
From $428 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 3
- 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 $428 per night (USD)Expedia
From $1680 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 4
- 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 $1680 per night (USD)VRBO
From $570 per night (USD)Expedia
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 $570 per night (USD)Expedia
From $520 per night (USD)VRBO
🏝 LOCAL LANDMARK. The BLUE HOUSE on PINE 🐬Casa Caliente🐬
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly Renovated. 🌀CASA CALIENTE 🌀 A spectacular and truly MAGICAL place to experience.🐬 AMI,fl T ...
From $520 per night (USD)VRBO
From $965 per night (USD)Expedia
Anna Maria Heated Pool Ocean View Hot Tub Short Walk To Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Palm Beach at AMI. This custom built, 5 Bedroom 4.5 Bath, home with Heated Pool and Spa will make you feel re ...
From $965 per night (USD)Expedia
From $1480 per night (USD)VRBO
Spoil yourself! Gulf front, heated pool, hot tub. Front row for sunsets-perfect!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Built on sand, designed for joy, beachfront, modern and ready for you and your crew! Nest on the Beach did not get damag ...
From $1480 per night (USD)VRBO
From $979 per night (USD)VRBO
Beachfront Mango Beach House on Bean Point in Anna Maria Florida
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Mango Beach House is an exceptional beach front paradise. White sugar sand, warm waters of the Gulf of Mexico are out y ...
From $979 per night (USD)VRBO
From $490 per night (USD)VRBO
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 $490 per night (USD)VRBO
From $482 per night (USD)VRBO
Cozy Cottage w private Beach Access, AC&WiFi - NorthEnd AMI. No hurricane damage
- Bedrooms:
- 1
- 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 $663 per night (USD)VRBO
Jacaranda Gem by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $663 per night (USD)VRBO
From $1197 per night (USD)VRBO
North End AMI, Pool,Ocean Views,Tropical Oasis and elevator. No hurricane Damage
- Bedrooms:
- 4
- 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 $1197 per night (USD)VRBO
From $553 per night (USD)VRBO
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 $553 per night (USD)VRBO
From $398 per night (USD)Expedia
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 $398 per night (USD)Expedia
From $386 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. Recently remodeled we are open for guests . Anna Maria Island vacatio ...
From $386 per night (USD)VRBO
From $1108 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 $1108 per night (USD)VRBO
From $421 per night (USD)VRBO
Turtle Cottage - Anna Maria Island
- Bedrooms:
- 1
- 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 $421 per night (USD)VRBO
From $856 per night (USD)Expedia
Reef Romance managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
It's all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, fou ...
From $856 per night (USD)Expedia
From $494 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 $494 per night (USD)VRBO
From $731 per night (USD)VRBO
The Happy Hibiscus Island Oasis with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $731 per night (USD)VRBO
From $456 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 $456 per night (USD)VRBO
From $366 per night (USD)Expedia
Perfect Anna Maria-20% off Aug/Sep\n 3 blocks to sugar sand beach. Heated pool.
- Bedrooms:
- 2
- 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 $366 per night (USD)Expedia
From $316 per night (USD)VRBO
Blue Heron Cottage - Anna Maria Island
- Bedrooms:
- 1
- 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 $316 per night (USD)VRBO
From $475 per night (USD)VRBO
Sept Deals! - Canal /Hot Tub/Htd Pool/ Dock/ AMIHomeRental
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
September Deals Sept 6 - 13, 2025 now $1,999/wk* plus fees & taxes Sept 13 - 20, 2025 now $1,999/wk* plus fees & taxes S ...
From $475 per night (USD)VRBO
From $665 per night (USD)VRBO
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite ...
From $665 per night (USD)VRBO
From $851 per night (USD)VRBO
Hear The Surf/Feel The Breeze... skip to beach!\nLocated on Anna Maria Island
- Bedrooms:
- 3
- 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 $851 per night (USD)VRBO
From $222 per night (USD)VRBO
Bungalow On The Bayou (Best Location on the Island)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a specta ...
From $222 per night (USD)VRBO
From $366 per night (USD)Expedia
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 $366 per night (USD)Expedia
From $788 per night (USD)VRBO
CabAnna Maria Beach Block 4 Bedroom 4.5 Bath
- Bedrooms:
- 4
- 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 $788 per night (USD)VRBO
From $521 per night (USD)VRBO
Aug 23-30 Deal - Waterfront/HotTub/ Pool/Dock/PuttGreen/Beach by AMIHomeRental
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Check out our Last Minute Summer Deals! - Aug 23 - 30, 2025 now $1,999/wk* plus fees & taxes - Sept 6 - 18, 2025 now $ ...
From $521 per night (USD)VRBO
From $678 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 $678 per night (USD)VRBO
From $282 per night (USD)Expedia
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $282 per night (USD)Expedia
From $443 per night (USD)VRBO
Spacious beach house with a beautiful view of the gulf
- Bedrooms:
- 2
- 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 $443 per night (USD)VRBO
From $208 per night (USD)Expedia
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 $208 per night (USD)Expedia
From $208 per night (USD)VRBO
FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to Cross!
- Bedrooms:
- 1
- 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 $208 per night (USD)VRBO
From $355 per night (USD)Expedia
4 Bed/2.5 Bath Duplex, FREE WiFi & Trolley, ONLY STEPS to Pristine Sandy...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
**ASK ABOUT LAST-MINUTE DEALS! Enjoy a simple, old-fashioned seaside vacation in this adorable duplex west ...
From $355 per night (USD)Expedia
From $525 per night (USD)VRBO
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 $525 per night (USD)VRBO
From $1083 per night (USD)Expedia
Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bikini Bottom by Anna Maria Life Vacation Rentals 302 Spring Ave, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1083 per night (USD)Expedia
From $525 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Beachview Retreat on Anna Maria! This conveniently located cottage is just steps away from white sandy, Gulf ...
From $525 per night (USD)VRBO
From $501 per night (USD)Expedia
Dog-Friendly 4 Mins to the Beach & Pine Ave - A Place in Paradise Unit B
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Place in Paradise Unit B by Anna Maria Island Accommodations Duplex in Anna Maria, Florida 34216 VR16-000529 Welcome ...
From $501 per night (USD)Expedia
From $233 per night (USD)VRBO
Family-Friendly Duplex Near Beaches & Local Shops - A Place In Paradise Unit A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Place In Paradise Unit A by Anna Maria Island Accommodations Duplex in Anna Maria, FL Welcome to A Place in Paradise ...
From $233 per night (USD)VRBO
From $208 per night (USD)Expedia
Pelican's Roost: Serene coastal retreat, in heart of Anna Maria Island life!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Pelican's Roost" – your ultimate coastal retreat on Anna Maria Island! Nestled off the lively Pine Avenue, t ...
From $208 per night (USD)Expedia
From $383 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea grape trees, hibiscus bushes and palm trees surround this pretty white-roofed daffodil-colored cottage that is just ...
From $383 per night (USD)VRBO
From $481 per night (USD)Expedia
September Golf Cart Special
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Sea Jay is a newly refreshed, canal front pool home located in the heart of Anna Maria! Enter the home through the kitch ...
From $481 per night (USD)Expedia
From $632 per night (USD)VRBO
September Golf Cart Special
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Blue Palm, your next vibrant home-away-from-home here in Anna Maria. Constructed in 2016 by luxury builders M ...
From $632 per night (USD)VRBO
From $344 per night (USD)Expedia
Coquina Cottage B by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Coquina Cottage B! Coquina Cottage B is exceptionally located at the northern end of Anna Maria Island, just ...
From $344 per night (USD)Expedia
From $1141 per night (USD)VRBO
Brand-new luxury Home with Pool and Spa, Bikes, just a 2-min walk to the beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Meet Me at Sunset by Anna Maria Island Accommodations Home in Anna Maria, Florida Highlights • Brand-new construction h ...
From $1141 per night (USD)VRBO
From $1013 per night (USD)Expedia
Anna Maria Beach House (AMIA)
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Highlights • Brand new home • Private pool and In-ground spa • Game room • Less than a 15-minute walk to the beach • Roo ...
From $1013 per night (USD)Expedia
From $1537 per night (USD)VRBO
Rooftop Deck - Anna Maria Beach House by SeaBreeze Vacation
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 8
Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat ...
From $1537 per night (USD)VRBO
From $1677 per night (USD)Expedia
Canal Front - From Dusk 'Til Dune by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one bl ...
From $1677 per night (USD)Expedia
From $574 per night (USD)VRBO
Becker's Beach Bungalow by A Shore Thing Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream getaway at Anna Maria Island! Nestled just one block away from the pristine shores of the beach, t ...
From $574 per night (USD)VRBO
From $681 per night (USD)Expedia
Water's Edge: Dog Friendly, Canal Front, Dock & Pool & Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Water's Edge by Anna Maria Life Vacation Rentals 221 Oak, Anna Maria, FL 34216 What You'll Love About This Home: Locati ...
From $681 per night (USD)Expedia
From $357 per night (USD)VRBO
Barefoot Mermaid 3, greatAMI location steps to the beach/fun on Pine Ave
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Barefoot Mermaid 3 a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Isl ...
From $357 per night (USD)VRBO
From $339 per night (USD)Expedia
Sunny home near the water with patio, streaming, washer/dryer, grill, fast WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
29 Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $339 per night (USD)Expedia
From $931 per night (USD)VRBO
Jersey Girl by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to this unique 5 bedroom Island Paradise! Jersey Girl features a main house with 3 bedrooms and 2 baths al ...
From $931 per night (USD)VRBO
From $1150 per night (USD)Expedia
Island Time on Cedar: 3 Houses to Beach! Dog Friendly! Pool by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Island Time on Cedar by Anna Maria Life Vacation Rentals 110 Cedar Ave, Anna Maria, FL 34216 What You'll Love About Thi ...
From $1150 per night (USD)Expedia
From $1439 per night (USD)VRBO
Brand-new luxury home with sparkling Pool, Bikes, 2-minute walk to the beach!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Moondance by AMI Locals Home in Anna Maria, Florida Highlights • Located on the Beach Block with Stunning Gulf Views ...
From $1439 per night (USD)VRBO
From $1274 per night (USD)Expedia
Brand New Luxury Home, Incredible Rooftop Deck and Pool - Total Package
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Total Package by AMI Locals Home in Anna Maria 34216 Welcome to Total Package! This elegant brand-new vacation home f ...
From $1274 per night (USD)Expedia
From $1053 per night (USD)VRBO
Rooftop Deck, Private Pool and Game room! Perfect for Families!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 8
Boundless Waves by Anna Maria Island Accommodations Anna Maria, Florida Welcome to Boundless Waves, an incredible vac ...
From $1053 per night (USD)VRBO
From $501 per night (USD)Expedia
Bimini Bay: 3 Blocks to Beach! Private Pool! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 $501 per night (USD)Expedia