Anna Maria Rentals
- From $745 per night (USD)
VRBO
Beautiful, well-maintained home w\/ heated private pool - walk to beach & dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sundance Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $745 per night (USD)VRBO
- From $596 per night (USD)
Expedia
High-end home w\/ heated private pool\/spa, courtyard, & floor-to-ceiling windows
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Dream Maker Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $596 per night (USD)Expedia
- From $646 per night (USD)
VRBO
Canalfront Island Gem with Private Heated Pool, Dock, Ping-Pong, & Putting Green
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Mermaid Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $646 per night (USD)VRBO
- From $112 per night (USD)
Expedia
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria's Finest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $112 per night (USD)Expedia
- From $488 per night (USD)
VRBO
Charming gulf-front home right on the beach - stunning views, dogs welcome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Dolphin Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $488 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Waterfront dog-friendly bungalow w\/ bay views - watch for dolphins from deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Grant's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $255 per night (USD)Expedia
- From $688 per night (USD)
VRBO
Incredible, spacious home with a private heated pool - close to the beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Le Paradis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $688 per night (USD)VRBO
- From $617 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 $617 per night (USD)VRBO
- From $333 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 $333 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Canalfront home w\/ WiFi, heated pool, dock & lanai - 2 blocks to the beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Heavenly Holly Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $370 per night (USD)Expedia
- From $820 per night (USD)
VRBO
Breezy canalfront home w\/ heated pool & dock - 3 blocks to Bean Point Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Paradise Pointe Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $820 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Adorable Cottage with Heated Pool - Fantastic Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Buttonwood Cottage by AMI Locals Home in Anna Maria, Florida Full of old Florida charm and recently restored, we welcom ...
From $370 per night (USD)Expedia
- From $1400 per night (USD)
VRBO
Gulf Front Home with Amazing Views!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Happy Ours by AMI Locals Home in Anna Maria, FL Highlights: • Gulf Front • Back porch with grill • Updated kitchen feat ...
From $1400 per night (USD)VRBO
- From $978 per night (USD)
Expedia
Enjoy \"Endless Summer\" at this awesome luxury beach house with your family!
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 14
Endless Summer by Anna Maria Island Locals Home in Anna Maria, FL Just one street over from Pine Ave Highlights: - Bea ...
From $978 per night (USD)Expedia
- From $508 per night (USD)
VRBO
Point's Hideaway - Beautiful Home w\/Stunning Sunset\/Water Views on Bean Point! Pool, Bar, Foosball!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Point's Hideaway! On Anna Maria Island (Anna Maria, FL) HIGHLIGHTS: - Kitchen, Dining, Living w/ TV - 1 King ...
From $508 per night (USD)VRBO
- From $843 per night (USD)
VRBO
Luxury home, close to the beach! Pool and Spa, great for families!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Freckled Fin by AMI Locals Home in Anna Maria, Florida VR19-000006 Welcome to Freckled Fin, a fun and luxurious vacati ...
From $843 per night (USD)VRBO
- From $1081 per night (USD)
VRBO
Serendipity Gulfront- gulf beach front
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell sear ...
From $1081 per night (USD)VRBO
- From $636 per night (USD)
Expedia
Water views- 4 bedroom\/2 bath
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sky by Serendipity is a unique, elevated island home with 4 bedrooms and 2 bathrooms. Conveniently located on the north ...
From $636 per night (USD)Expedia
- From $1696 per night (USD)
VRBO
TripleTail- beachfront 4\/4
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
4 bedroom 4 bath Beach Front Home with Panoramic views of the Ocean and Skyway Bridge. Watch dolphins swim and play in y ...
From $1696 per night (USD)VRBO
- From $720 per night (USD)
Expedia
Canal front home with a pool and boat dock!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Canalfront with dock • 5-minute walk to the beach • Private pool • Putting green • Pool Table and Ping Po ...
From $720 per night (USD)Expedia
- From $925 per night (USD)
VRBO
Historic 1924 Luxury Beach Home with Large Heated Pool 3 Houses to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Sand Castle located just a few steps from the Gulf beaches of Anna Maria Island. Built in 1924, the Castl ...
From $925 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Idyllic Holiday Properties is a small friendly holiday company offering an honest and efficient service for our privatel ...
From $393 per night (USD)Expedia
- From $385 per night (USD)
VRBO
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
OHasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are im ...
From $385 per night (USD)VRBO
- From $534 per night (USD)
Expedia
C-View by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
C-View is the perfect island getaway for your family vacation. Conveniently located within walking distance to Anna Mari ...
From $534 per night (USD)Expedia
- From $1500 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 $1500 per night (USD)VRBO
- From $393 per night (USD)
Expedia
Colorful beach cottage w\/ heated private pool & grill area - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sea's The Day Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $393 per night (USD)Expedia
- From $584 per night (USD)
VRBO
Waterfront home near beaches with private heated pool, spa, and more
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Surrounded By Sea Breezes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $584 per night (USD)VRBO
- From $358 per night (USD)
Expedia
Sunny dog-friendly cottage with spacious patio and grill, steps from the beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Seashell Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $358 per night (USD)Expedia
- From $476 per night (USD)
VRBO
La Cocolia in Anna Maria
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house ...
From $476 per night (USD)VRBO
- From $393 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 $393 per night (USD)VRBO
- From $486 per night (USD)
VRBO
North End of Anna Maria Island with Spectacular Views from the Primary EnSuite
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just ...
From $486 per night (USD)VRBO
- From $293 per night (USD)
Expedia
Seas The Day: North End Canal Front, Fishing Dock & Kayaks by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
522 Bayview Place, Anna Maria, FL 34216 What You'll Love About This Home: Location - North End on a Canal with Private ...
From $293 per night (USD)Expedia
- From $1058 per night (USD)
VRBO
Gulf Shore Retreat managed by Beach Retreats
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the ...
From $1058 per night (USD)VRBO
- From $894 per night (USD)
Expedia
Casa Mariposa - Luxury Butterfly Garden, Steps to Pine Ave, Pool\/Spa, Bikes, 4 Houses to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Mariposa! On Anna Maria Island (Anna Maria, FL) HIGHLIGHTS: - Open layout and spacious Kitchen, Dining ...
From $894 per night (USD)Expedia
- From $793 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 $793 per night (USD)VRBO
- From $1018 per night (USD)
Expedia
My Private Beach: Waterfront Pool Home on the Bay by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
826A South Bay Blvd., Anna Maria, FL 34216 What You'll Love About This Home: Location! Your own private sandy beach on ...
From $1018 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Wake up on the waters of Tampa Bay in a north Anna Maria home.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Two story elevated beach home with gorgeous water views, steps from park and two fishing piers. Enjoy meals in the separ ...
From $250 per night (USD)VRBO
- From $225 per night (USD)
Expedia
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
301 Poinsettia Rd., Anna Maria, FL 34216 What you'll love about this home: Location! On the North End of Anna Maria 2 ...
From $225 per night (USD)Expedia
- From $507 per night (USD)
VRBO
July 5th - 11th Still Available!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
DESCRIPTION: It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the ...
From $507 per night (USD)VRBO
- From $978 per night (USD)
Expedia
Toes in the Water: North End, West of Gulf, Steps to Beach, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
110 Palm Ave, Anna Maria, FL 34216 What You'll Love About This Home: 4 Houses to the Beach! West of Gulf! No Street to ...
From $978 per night (USD)Expedia
- From $600 per night (USD)
VRBO
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly redesigned elevated 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art qua ...
From $600 per night (USD)VRBO
- From $400 per night (USD)
Expedia
Tropical Landscaped Beach Cottage with Heated Jetted Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to SURF’S UP, located one block from the sugary white sand beaches on the desirable north end of the Anna Maria. ...
From $400 per night (USD)Expedia
- From $249 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 $249 per night (USD)VRBO
- From $382 per night (USD)
Expedia
Casa Posada - So Close You Can Hear the Waves! Historic Beach Cottage w\/ Beach Gear
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Posada! On Anna Maria Island (Anna Maria, FL) Managed by Once Upon A Beach Vacation Rentals, a locally o ...
From $382 per night (USD)Expedia
- From $500 per night (USD)
VRBO
La Bella Bungalow Beachfront, nostalgic beach cottage ambiance 🌅
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
❗ Flexible check-in days throughout most of the year. Sundays are not available as check-in days. 🤩 If you love t ...
From $500 per night (USD)VRBO
- From $625 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 $625 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Perfect summer vacation home! Close to Bean Point, great pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Feelin' Salty by AMI Locals Home in Anna Maria, FL Highlights: - Pool - Ping pong table - Open concept layout with ple ...
From $275 per night (USD)VRBO
- From $910 per night (USD)
Expedia
Luxury Home with Pool, Spa, Rooftop, a block from the Beach - Paradise Bound
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Paradise Bound by AMI Locals Home in Anna Maria, Florida VR21-000036 Welcome to Paradise Bound, a four bedroom and four ...
From $910 per night (USD)Expedia
- From $459 per night (USD)
VRBO
Sea Whisper in north-end Anna Maria with private dock and pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Sea Whisper, our brand new renovated home with 3 bedrooms / 3 bathrooms, private dock, swimming pool, and spa ...
From $459 per night (USD)VRBO
- From $360 per night (USD)
Expedia
Charming house with private heated pool, lanai. Great location to beach & shops
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Quaint Northshore Cottage a few blocks from the village of Anna Maria and the Gulf of Mexico beaches. Sapphire Surf is ...
From $360 per night (USD)Expedia
- From $376 per night (USD)
VRBO
BEAUTIFUL DIRECT BAY FRONT, Steps to Village, FREE WiFi\/Trolley, Dog*(See...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
**ASK ABOUT LAST-MINUTE DEALS! Avoca...a Gaelic word that means "the meeting of the waters," and the perfe ...
From $376 per night (USD)VRBO
- From $370 per night (USD)
Expedia
Beautifully remodeled 3 bedroom luxury home, just steps to BEACH! Brand-new Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Deckhouse by AMI Locals Home in Anna Maria, FL Highlights: • Brand new pool with spa • Multiple decks • Keurig cof ...
From $370 per night (USD)Expedia
- From $1061 per night (USD)
VRBO
Luxurious Private Canal Front Home with Resort Style Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Banyan Manor by AMI Accommodations Private home in Anna Maria, FL 1.5 Blocks to Beach Highlights: • Brand new canal f ...
From $1061 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Beautiful North-End Home! Pool with In-ground Spa, Shuffleboard!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Carefree Cay by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000412 Welcome to Carefree Cay, a ...
From $439 per night (USD)Expedia
- From $750 per night (USD)
Expedia
Private Canal Home with Spacious Pool and Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Fancy Flamingo (formerly The Little Mermaid) 319 Hardin Ave Anna Maria VR20-000005 3 Blocks to the Beach Welcome to th ...
From $750 per night (USD)Expedia
- Click For Pricing
Expedia
Ground Level Cottage with Pool and Hot Tub, 1 Block to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Mermaid's Treasure by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000363 Welcome to Mermaid's T ...
Click For PricingExpedia
- From $1009 per night (USD)
VRBO
Luxury Home with Heated Pool, Hot Tub, and Entertainment Area!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Less than a 5-minute walk to the beach • Private pool and hot tub • Game area • Multiple balconies ...
From $1009 per night (USD)VRBO
- From $721 per night (USD)
Expedia
Beautiful Canal Front Home with Putt-Putt Green, Only 5 Blocks to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lavender Lagoon by Anna Maria Island Accommodations Home in Anna Maria, FL 34217 VR22-000006 Welcome to Lavender Lagoo ...
From $721 per night (USD)Expedia
- From $443 per night (USD)
VRBO
Tropical Oasis with Private Pool and Game Room, 3 Blocks to Beach or Bay!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 10-minute walk to the beach or bay • Private Pool • Ping Pong Table • Washer and Dryer Pel ...
From $443 per night (USD)VRBO
- From $972 per night (USD)
Expedia
Spacious Home Perfect for Family Vacation with Pool and Putting Green
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Private Pool and Hot Tub • Less than a 5-minute walk to the beach • Elevator • Putting Green • Pool Ta ...
From $972 per night (USD)Expedia
- From $479 per night (USD)
VRBO
Home with Pool and Outdoor Amenities near the Bay and Beach - North End Chic
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
North End Chic by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000361 Welcome to North End Chi ...
From $479 per night (USD)VRBO
- From $275 per night (USD)
Expedia
Spacious Home with Private Pool, Just 1 Block to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Starfish Beach by AMI Accommodations Home in Anna Maria, FL 1 Block to Beach Highlights: - Private pool surrounded by ...
From $275 per night (USD)Expedia
- From $607 per night (USD)
VRBO
Canal Front Home With Dock Just 4 Blocks to Beach! - Blue Turtle
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue Turtle by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000118 Welcome to Blue Turtle, a ...
From $607 per night (USD)VRBO
- From $505 per night (USD)
Expedia
Private Home with Heated Pool, Only 3 Blocks to Bean Point
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Azure by AMI Accommodations Private home in Anna Maria, FL 3 Blocks to Bean Point Highlights: • Sea inspired hues of ...
From $505 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Island Home with Private Pool, Oversized Front Porch, and Poolside Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 10-minute walk to the beach • Private pool • Ping pong table • Outdoor shower • Washer an ...
From $450 per night (USD)VRBO
- From $500 per night (USD)
Expedia
Beautiful Guest House Near the Beach with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 5-minute walk to the beach • Pool Anna Maria Guest House 212 by Anna Marie Accommodations ...
From $500 per night (USD)Expedia
- From $351 per night (USD)
VRBO
Private Bungalow with Pool, Perfect for Family Vacations! - Hav'Anna Daydreamin
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hav'Anna Daydreamin by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000403 Welcome to Hav'Ann ...
From $351 per night (USD)VRBO
- From $359 per night (USD)
Expedia
Guest House in the Business District with Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Anna Maria Guest House 317 by Anna Maria Accommodations Home in Anna Maria, FL 34216 Welcome to Anna Maria Guest House ...
From $359 per night (USD)Expedia
- From $727 per night (USD)
VRBO
Canal Home With Private Pool and Dock, 2 Blocks to Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Canal Front with Dock • 5-minute walk from Beach • Private Pool and Hot Tub • Outdoor Shower Beach Hou ...
From $727 per night (USD)VRBO
- From $871 per night (USD)
Expedia
Canal Front Home with 60ft Dock and Heated Pool\/Spa!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights * 6 NEW KING SIZE BEDS, INCLUDING A FUN TRIPLE KING BUNK BED! NEW BEDDING * SONOS MUSIC SYSTEM WITHIN HOME ...
From $871 per night (USD)Expedia
- From $495 per night (USD)
VRBO
Canal Home with Private Dock and Pool with Outside Dining!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • Canal-front • Private Pool • Less than a mile from the beach • Washer and dryer • Ping pong table H ...
From $495 per night (USD)VRBO
- Click For Pricing
Expedia
Private Home with Tropical Landscaping and Heated Pool, Just 2 Blocks To Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • 7-minute walk from Beach • Private Pool • Outdoor Shower Bimini Bay by Anna Maria Island Accommodation ...
Click For PricingExpedia
- From $475 per night (USD)
VRBO
Private Home with Pool and Hot Tub, just 5 Houses to the Water!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beach Baby by Anna Maria Island Accommodations Private home in Anna Maria, Florida 5 Houses to Beach! Highlights: • J ...
From $475 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Cottage with Private Pool, Tropical Landscaped Backyard, Near Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Highlights • 7-minute walk to the beach • Private Pool • 1-minute walk to Pine Ave • Outdoor shower Covey Cottage 418 ...
From $450 per night (USD)Expedia
- From $323 per night (USD)
VRBO
Beautiful Ground Level Home with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Rest-A-Shore by Anna Maria Island Accommodations Home in Anna Maria, FL 1.5 Block to Bean Point Beautiful, Quiet, Gro ...
From $323 per night (USD)VRBO
- From $323 per night (USD)
Expedia
Private Home with Pool and Hot Tub, 2 Blocks to Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Highlights • 3-minute walk to the beach • Private pool and hot tub • Outdoor shower • Washer and dryer Little Pink Hou ...
From $323 per night (USD)Expedia
- Click For Pricing
VRBO
Quiet North End Home, One Block to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 10-minute walk to the beach • Private pool and hot tub • Outdoor shower Island Memories b ...
Click For PricingVRBO
- From $655 per night (USD)
Expedia
Canal Front Home with Private Pool and Spa, 2 Blocks to Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Triple Play by AMI Accommodations Home in Anna Maria, FL 2 Blocks to Beach Highlights: - Canal front - 4 1/2 minute ...
From $655 per night (USD)Expedia
- From $382 per night (USD)
VRBO
Ground Level Home with Saltwater Pool, 2 Blocks to Beach! - Pink Palm Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Pink Palm Bungalow by Anna Maria Island Accommodations Home in Anna Maria, FL 34217 VR16-000353 Welcome to Pink Palm ...
From $382 per night (USD)VRBO
- From $601 per night (USD)
Expedia
Canal View Home with Heated Pool, Across Street From Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Canal front with a dock that can accommodate a craft up to 25ft • Private Pool • Washer and dryer Liv ...
From $601 per night (USD)Expedia
- From $748 per night (USD)
VRBO
Private Home with Pool and Game Room, 1 Block to Beach! - Dolphin Pointe
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Dolphin Pointe by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000318 Welcome to Dolphin Poi ...
From $748 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Beautiful Condo on Pine Ave, 2 Blocks to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
High Tide Haven by Anna Maria Island Accommodations 306 Pine Ave Anna Maria, FL 34216 Welcome to High Tide Haven where ...
From $315 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Adorable Cottage with Covered Balconies and Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Social Nest by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 Welcome to Social Nest, a second-level ho ...
From $300 per night (USD)VRBO
- From $501 per night (USD)
Expedia
Perfectly Located Near Bay Beaches and Pine Ave!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 5-minute drive to the beach • Private pool and outdoor shower • Less than a 5-minute walk to ...
From $501 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Spacious Canal Home Perfect For Family Vacations!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Canal Front • 1-mile from the Beach • Private Pool and Hot Tub • Ping pong table Gypsy Sol by ...
From $435 per night (USD)VRBO
- From $859 per night (USD)
Expedia
Private Home with Rooftop Deck, Pool, and Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • 2-minute walk from the Beach • Private Pool and Hot Tub • Roof Top Deck Called In Sic by Anna Maria Isl ...
From $859 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Shared Pool, Private Patio, Only 2 Houses to the Beach - Sand and Sea 113 B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand and Sea 113 B by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000423 Welcome to Sand and Se ...
From $313 per night (USD)VRBO
- From $467 per night (USD)
Expedia
Home with Private Pool Just 1 Block from the Beach! - Hav'Anna Hideaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Hav'Anna Hideaway by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000402 Welcome to Hav'Anna Hide ...
From $467 per night (USD)Expedia
- From $1399 per night (USD)
VRBO
Beautiful North-End Home with Heated Pool and Hot Tub, 100 Steps to the Beach!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Water Colors by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 100 Steps to Beach Highlights: -Situated ...
From $1399 per night (USD)VRBO
- Click For Pricing
Expedia
3 Houses From the Beach! Heated Pool, Game Room, and Amazing Gulf Views!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Time by Anna Maria Island Accommodations Home in Anna Maria, FL 34216 VR16-000389 Welcome to Island Time! 3 Ho ...
Click For PricingExpedia
- From $450 per night (USD)
VRBO
Private Home 1 Block to Beach with Pool and Hot Tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 3-minute walk from Beach • Private pool and hot Tub • Outdoor shower • Washer and dryer Beach You To I ...
From $450 per night (USD)VRBO
- From $867 per night (USD)
Expedia
Newly Built Home with Private Pool, 1\/2 Block to Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 2-minute walk to the beach • Private pool and hot tub • Game room • Elevator • Washer and dryer Coral K ...
From $867 per night (USD)Expedia
- From $657 per night (USD)
VRBO
Private pool, 1 Block to beach, Putting Green - Lady from the Sea
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 10-minute walk from the beach • Private pool • Putting Green • Outdoor living space • Nea ...
From $657 per night (USD)VRBO
- From $440 per night (USD)
Expedia
Private Home with Caged Pool, 1 Block to Beach, Great for Family!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • Less than a 5-minute walk to the beach • Private pool • Separate guest suite • Hammock • Washer and d ...
From $440 per night (USD)Expedia
- Click For Pricing
Expedia
Family home with Tiki-hut, Pool, Spa, and Waterslide-Day Dream
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Day Dream by Anna Maria Island Accommodations Home in Holmes Beach, FL 34217 VRC16-000155 Welcome to Day Dream, an invi ...
Click For PricingExpedia
- From $1160 per night (USD)
Expedia
Luxury family vacation home with rooftop deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Poseidons Palace Home in Holmes Beach, FL Less than 1 Block to the beach Welcome to the ultimate in Large Family luxu ...
From $1160 per night (USD)Expedia
- From $989 per night (USD)
VRBO
Gorgeous single-family home, just 300 steps from the Gulf sands!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Octopus Cottage 209 69th St Holmes Beach, FL 34217 Less than 300 steps to the beach! Welcome to Octopus Cottage! This ...
From $989 per night (USD)VRBO
- From $265 per night (USD)
Expedia
Beach Condo with Shared Pool, Only 2 Houses to the Beach - Sand And Sea 113 A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Sand And Sea 113 A by Anna Maria Island Accommodations Condo in Anna Maria, FL 34216 VR16-000423 Welcome to Sand and Se ...
From $265 per night (USD)Expedia
- From $546 per night (USD)
VRBO
Home with Private Pool, Just Over a Block to Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Highlights • 5-minute walk to the beach • Private pool • Outdoor shower • Washer and dryer Casa Allegria 209 Archer W ...
From $546 per night (USD)VRBO
- From $330 per night (USD)
Expedia
Adorable home in the best location! Saltwater pool and hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Highlights • 3-minute walk to the beach • Private pool and hot tub • 2 Outdoor showers • Near free island trolley stop ...
From $330 per night (USD)Expedia