Anna Maria Rentals
- From $573 per night (USD)
VRBO
Sand Dollar Dream - Remodeled Canal Private Pool Home - By Island Real Estate Va
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The perfect spot for your next island getaway, “Sand Dollar Dream” is a gorgeous canal front private pool home with ever ...
From $573 per night (USD)VRBO
- From $268 per night (USD)
Expedia
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Villa in the heart of Anna Maria! Palm Court Villas are located in the heart of Anna Maria Village with a short st ...
From $268 per night (USD)Expedia
- From $537 per night (USD)
VRBO
Dog friendly home with heated pool and balconies! Great location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spring Haven by Anna Maria Island Locals Home in Anna Maria, FL Highlights: - Heated pool surrounded by loungers and lu ...
From $537 per night (USD)VRBO
- From $495 per night (USD)
Expedia
AMI Bay Breeze: Heated pool, outdoor bar, beautifully updated.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to AMI Bay Breeze! This newly renovated, 3 bedroom 2 bathroom home is the perfect escape for your next vacation ...
From $495 per night (USD)Expedia
- From $962 per night (USD)
VRBO
Gorgeous island luxury home just one block to the Beach! Come stay with us!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Tahiti Bay by AMI Locals Home in Anna Maria, FL VR16-000466 Welcome to Tahiti Bay, a stunning vacation rental wi ...
From $962 per night (USD)VRBO
- From $365 per night (USD)
Expedia
Bay-facing condo with amazing views and heated pool - beach across the street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
South Bay Inn 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $365 per night (USD)Expedia
- From $609 per night (USD)
VRBO
Bayside Bliss by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the serene luxury of Bayside Bliss which is a fully remodeled three-bedroom/three-bathroom, ground level cott ...
From $609 per night (USD)VRBO
- From $379 per night (USD)
Expedia
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
The Sea Spray Cottages are an adorable group of Units located in the North End of Anna Maria, West of Gulf Drive and onl ...
From $379 per night (USD)Expedia
- From $907 per night (USD)
VRBO
Golf Cart, Bimini Cove by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show ...
From $907 per night (USD)VRBO
- From $706 per night (USD)
Expedia
Salty C Cottage Spectacular canal front home with pool and hot tub!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous and recently remodeled 4 bedroom, 3 1/2 bath ground level home with amazing designer touches and finishes throu ...
From $706 per night (USD)Expedia
- Click For Pricing
Expedia
Canario Cottage by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Newly Renovated Bathrooms and Fabulous New Flooring and updates throughout the whole property! Welcome to Canario Cotta ...
Click For PricingExpedia
- From $457 per night (USD)
Expedia
Vibrant Island Home w\/ Pool, 1 Block to Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
A tropical paradise awaits when you book this stylish Anna Maria retreat! Ideally situated just 0.1 miles from the gorge ...
From $457 per night (USD)Expedia
- From $530 per night (USD)
VRBO
A Bay From It All: North-end pool home 3 Blocks to Bean Point!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Leave the stress of everyday life and get "A Bay From it All"! This amazing 3 bedroom / 3 full bathroom home on the cove ...
From $530 per night (USD)VRBO
- From $371 per night (USD)
Expedia
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
MI Oasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are i ...
From $371 per night (USD)Expedia
- From $270 per night (USD)
VRBO
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
❗ Flexible check in days for most of the year--with the exception of holidays. Friday arrivals and departures during Pe ...
From $270 per night (USD)VRBO
- From $665 per night (USD)
Expedia
Luxury Home with Pool and Dock for Fishing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Pelican's Nest by AMI Locals Home in Anna Maria, FL Features: • Private Pool • Gorgeous Brand New Construction home • ...
From $665 per night (USD)Expedia
- From $325 per night (USD)
VRBO
Charming 2br \/ 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Built in 1924, Sunset Cottages’ beautifully maintained woodwork coupled with updated amenities delivers an authentic Flo ...
From $325 per night (USD)VRBO
- From $469 per night (USD)
Expedia
Island Time: AMI North End, Pool, Close to City Pier & Pine Ave by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home Location! In the heart of Anna Maria, and withi ...
From $469 per night (USD)Expedia
- From $1905 per night (USD)
VRBO
Incredible luxury canal front home with lazy river style pool! -Winding Waves
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 8
Winding Waves by AMI Locals Home in Anna Maria, Florida VR20-000041 Your luxury beach vacation awaits at Winding Wav ...
From $1905 per night (USD)VRBO
- From $800 per night (USD)
Expedia
Bean Point Beachfront- Beachfront 4 bedroom private home with pool\/spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
At A Glance Gulf-Front, Beach side Home Spacious Backyard Deck with Covered Dining Area, TV & Gas BBQ Grill NEW Private ...
From $800 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Sunset Point- Beachfront 4 bedroom with private pool with views
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Point 765 North Shore Drive, Anna Maria What you will love about this property: • Direct Gulf Front • Beach is ...
From $500 per night (USD)VRBO
- From $1363 per night (USD)
Expedia
Spacious home with heated pool, jacuzzi, and rooftop deck
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
From Dusk 'Til Dune by AMI Locals Home in Anna Maria, FL 34216 Welcome to From Dusk 'Til Dune, a canal front home wit ...
From $1363 per night (USD)Expedia
- From $417 per night (USD)
VRBO
Golf Cart, Stonehenge by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN 11/18/23 - 08/03/24 and 4/26/25 - 12/31 ...
From $417 per night (USD)VRBO
- From $450 per night (USD)
Expedia
*NEW LISTING* Boutique Spanish-Style Villa - perfect for family\/couple getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This unique, beautifully appointed Boutique Spanish Style Villa on the North End of Anna Maria Island is a perfect getaw ...
From $450 per night (USD)Expedia
- Click For Pricing
Expedia
Waterfront duplex with lagoon views & private patio - walk to beach\/bars\/dining
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Manatee Retreat - A Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
Click For PricingExpedia
- From $81 per night (USD)
Expedia
2nd-floor condo across the street from the beach with heated pool, balcony, W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
South Bay Inn 4 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $81 per night (USD)Expedia
- From $922 per night (USD)
VRBO
Island Therapy: Pool, Canal, Dock, Outdoor Fun & Games!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
103 Gull Drive, Anna Maria, FL 34216 What You'll Love About This Home: Location! North End, On Canal! 4 Bedroom / 3 Bath ...
From $922 per night (USD)VRBO
- From $573 per night (USD)
Expedia
Tinas Piece of Paradise - 4BR private pool home - Anna Maria Island - By Island
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Pi ...
From $573 per night (USD)Expedia
- From $669 per night (USD)
VRBO
Reel Deal: Water Views, Elevator, Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Reel Deal by Anna Maria Life Vacation Rentals 505 S Bay, Anna Maria, FL 34216 What You'll Love About This Home: Locatio ...
From $669 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Pirates Lookout by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Pirates Lookout, a slice of island paradise. This eclectic, surfer-chic carriage house is nestled on Anna Mar ...
From $400 per night (USD)Expedia
- From $1180 per night (USD)
VRBO
Pirates Bounty by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
The ultimate 5 bedroom beachfront retreat on the secluded and desirable North end of Anna Maria. Only steps to the Rod a ...
From $1180 per night (USD)VRBO
- From $832 per night (USD)
Expedia
Pirates Bay by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beachfront pool home on the secluded and desirable North end of Anna Maria just steps to the Rod and Reel Pier! *Featur ...
From $832 per night (USD)Expedia
- From $268 per night (USD)
VRBO
Manatee Retreat Unit B by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Drive through the gated driveway with a manatee on it and you'll enter Manatee Retreat. This duplex is a private getaway ...
From $268 per night (USD)VRBO
- From $800 per night (USD)
Expedia
4 Bed 4 Ba 4 Homes to Beach! New home\/heated pool\/spa\/SUP\/kayaks\/bikes\/much more
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Completely remodeled 4 bedroom, 4 bathroom relaxing original beach home. Two king sized bedrooms upstairs each with lux ...
From $800 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Blue Waters~Anna Maria, Private Home, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Are you looking for Peace and Quiet and a place you can bring your dog too? Look no further than "Blue Waters." This lo ...
From $175 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Anna Maria Beach House Steps to Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The perfect beach getaway, centrally located on the island. Situated one short block from the most beautiful part of the ...
From $275 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Dave's Treasure Condo with Private Dock boat in AMI
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Dave's Treasure Condo, a cozy retreat located on the first floor of building number six with a great water vi ...
From $214 per night (USD)VRBO
- From $529 per night (USD)
Expedia
White Palms by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Introducing White Palms, an exquisite coastal retreat nestled in the coveted north end of Anna Maria Island. * Private ...
From $529 per night (USD)Expedia
- From $537 per night (USD)
VRBO
Casa Cay by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Casa Cay! This Bay front pool home on Anna Maria Island sounds like an absolute paradise! With ...
From $537 per night (USD)VRBO
- From $212 per night (USD)
Expedia
Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you're longing to take a step back in time when Florida was about lazy beach days and ocean breeze evenings then look ...
From $212 per night (USD)Expedia
- From $3099 per night (USD)
VRBO
Lap of Luxury by Duncan Real Estate
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lap of Luxury! This home is new as of 2022 and has been meticulously built and designed to create a spa ...
From $3099 per night (USD)VRBO
- From $371 per night (USD)
Expedia
Heated Pool & Spa FREE WiFi & Trolley Close to Beach Dock your Boat!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
What a splendid retreat! This canal-front home in Anna Maria offers everything you could dream of for a relaxing and mem ...
From $371 per night (USD)Expedia
- From $337 per night (USD)
VRBO
New List: Great Location water\/canal side near Bean Point for long-term stay.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
New Listing-Location, location! North end, single level canal home ready for seasonal longer stay guests (30 day min bu ...
From $337 per night (USD)VRBO
- From $699 per night (USD)
Expedia
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 $699 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Beachfront Paradise w\/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The home has a private be ...
From $350 per night (USD)VRBO
- From $619 per night (USD)
VRBO
North end canal front home ,tiki hut, dock, heated pool, spa,beaches....
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. Thi ...
From $619 per night (USD)VRBO
- From $507 per night (USD)
VRBO
Waterfront POOL home just Steps to Pine Ave and Beaches in Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Anna Maria Beach Vacations brings you this fabulous private pool home in Anna Maria Florida. It boasts, 2 Bedroom and 2 ...
From $507 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Island Living, refreshing outdoor shower and pool , pet friendly if approved
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Our vacation home is 1 1/2 blocks to either the Gulf of Mexico or Tampa Bay. We have remodeled the kitchen and added a ...
From $315 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Top Rated Anna Maria Florida Vacation Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Our Sassy Seahorse has been rated as one of the top 15 out of 260 vacation rentals by Island Real Estate. Our 5-Star r ...
From $339 per night (USD)VRBO
- From $150 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 $150 per night (USD)VRBO
- From $1200 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 $1200 per night (USD)VRBO
- From $5110 per night (USD)
Expedia
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 $5110 per night (USD)Expedia
- From $618 per night (USD)
VRBO
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 $618 per night (USD)VRBO
- From $335 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 $335 per night (USD)VRBO
- From $365 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 $365 per night (USD)VRBO
- From $415 per night (USD)
VRBO
Minutes Walk to Bean Point and Rod & Reel Pier!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sweet vintage 1950's bungalow/cottage with all the charm of the island! Beautifully decorated and located on the island' ...
From $415 per night (USD)VRBO
- From $178 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 $178 per night (USD)VRBO
- From $464 per night (USD)
VRBO
Anna Maria Island Rentals - Beach Front - \"Angels Envy\"
- 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 $464 per night (USD)VRBO
- From $331 per night (USD)
VRBO
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 $331 per night (USD)VRBO
- From $1400 per night (USD)
VRBO
New Home 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 $1400 per night (USD)VRBO
- From $733 per night (USD)
VRBO
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 $733 per night (USD)VRBO
- From $1087 per night (USD)
Expedia
Anna Maria Northshore beauty !\" Come for the sun, stay for the fun!\"
- 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 $1087 per night (USD)Expedia
- From $375 per night (USD)
VRBO
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 $375 per night (USD)VRBO
- From $499 per night (USD)
VRBO
Bean Point Beach Cottage - Same street as Rod & Reel Pier & beach! New Listing
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
(NEW LISTING!) Vacation at Anna Maria Island with the most beautiful white sands beach and emerald green waters in the w ...
From $499 per night (USD)VRBO
- From $160 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 $160 per night (USD)VRBO
- From $925 per night (USD)
VRBO
BEACH NEST! Free bikes+2 tandem kayaks+beach cart+hot tub+dock+heated pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Ahhhh-welcome to Beach Nest! We look forward to welcoming you and yours! Ready to satisfy that oh-my-gosh-we-need-a-vac ...
From $925 per night (USD)VRBO
- From $1259 per night (USD)
VRBO
Casa Amiga managed by Beach Retreats
- Bedrooms:
- 5
- 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 $1259 per night (USD)VRBO
- From $1126 per night (USD)
VRBO
A Shore Thing - Second To None Spacious Waterfront Luxury! Dock, Pool, Spa, Rooftop Water Views!
- Bedrooms:
- 7
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to A Shore Thing! On Anna Maria Island (Anna Maria, FL) A waterfront luxury home just a few blocks from the pri ...
From $1126 per night (USD)VRBO
- From $502 per night (USD)
VRBO
LOCATION! -Bean Point area w\/pool. PANORAMIC WATER VIEW. Walk to Beach and town!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome! This home is booked WEEKLY from Sat-Sat.....usually. Please take note of maximum occupancy. We are registered ...
From $502 per night (USD)VRBO
- From $1039 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 $1039 per night (USD)Expedia
- From $393 per night (USD)
VRBO
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $393 per night (USD)VRBO
- From $1200 per night (USD)
VRBO
Dragonfly - Southern charm on the North end of Anna Maria Island
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Extensively renovated in 2016, Dragonfly is a private retreat located right across the street from the sugary white sand ...
From $1200 per night (USD)VRBO
- From $474 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 Rod and Reel Pier, ...
From $474 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Sunset Shores: 3 BR, 2.5 BA House in Anna Maria, Sleeps 6
- 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 $453 per night (USD)Expedia
- From $792 per night (USD)
VRBO
The Oasis at AMI: 4 BR, 3.5 BA House in Anna Maria, Sleeps 8
- 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 ...
From $792 per night (USD)VRBO
- From $747 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 $747 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Going Coastal by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $288 per night (USD)VRBO
- From $691 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 $691 per night (USD)Expedia
- From $1186 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 $1186 per night (USD)VRBO
- From $450 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 $450 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Secluded Bungalow on Anna Maria`s North End!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Pine Avenue HideAway is a secluded Beach Bungalow tucked away on Historic Pine Avenue on Anna Maria's North End. Conveni ...
From $250 per night (USD)VRBO
- From $781 per night (USD)
VRBO
Bateman's - Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Bateman's! On Anna Maria Island (Anna Maria, FL) 2543 sq. ft. HIGHLIGHTS: - Open layout and spacious Kitche ...
From $781 per night (USD)VRBO
- From $308 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 $308 per night (USD)VRBO
- From $390 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 $390 per night (USD)VRBO
- From $1006 per night (USD)
VRBO
Vitamin Sea managed by Beach Retreats
- 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 $1006 per night (USD)VRBO
- From $385 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 $385 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Dog-friendly beach bungalow with WiFi, private heated pool, balcony, and lanai
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Holly Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $339 per night (USD)VRBO
- From $353 per night (USD)
VRBO
Charming Beach house sits amongst huge Banyan Trees, walk to beach & Pine Ave.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
****UP TO 8 PEOPLE WITH ADDITONAL PRIVATE SUITE, ASK OWNER FOR AVAILABILITY**** Voted a Tropical paradise, feels like y ...
From $353 per night (USD)VRBO
- From $460 per night (USD)
VRBO
Pete's Blue Heaven: 4 BR, 2 BA House in Anna Maria, Sleeps 8
- 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 $460 per night (USD)VRBO
- From $1114 per night (USD)
Expedia
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 $1114 per night (USD)Expedia
- From $271 per night (USD)
VRBO
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 $271 per night (USD)VRBO
- From $199 per night (USD)
Expedia
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 $199 per night (USD)Expedia
- From $143 per night (USD)
VRBO
☀️🌊🐟❤️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 $143 per night (USD)VRBO
- From $1298 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 $1298 per night (USD)VRBO
- From $388 per night (USD)
VRBO
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 $388 per night (USD)VRBO
- From $503 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 $503 per night (USD)Expedia
- From $470 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 $470 per night (USD)VRBO
- From $600 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 $600 per night (USD)VRBO
- From $930 per night (USD)
VRBO
⚓Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool!⚓⛳🏖🌅
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" *Construc ...
From $930 per night (USD)VRBO
- From $550 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 $550 per night (USD)VRBO