Anna Maria Rentals
From $972 per night (USD)VRBO
Heavenly Hideaway, 3-bdrm house 5 min walk to the beach in beautiful Anna Maria
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Heavenly Hideaway, a Newly Renovated, exquisite canal-front vacation home featuring three bedrooms and three ...
From $972 per night (USD)VRBO
From $1139 per night (USD)Expedia
An \"Old Florida\" home, with private, sandy beach and sparkling green\/blue water.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
ENJOY PARADISE AT THIS UNIQUE, OLE FLORIDA HOME, NEWLY RENOVATED TO SHOW OFF ITS FLORIDA CHARM, LOCATED DIRECTLY ON THE ...
From $1139 per night (USD)Expedia
From $1314 per night (USD)VRBO
Pier to Pier Paradise by Beach Boutique Rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
This stunning 4-bedroom home, aptly named Pier to Pier Paradise, offers breathtaking views of the Bay, luxury amenities, ...
From $1314 per night (USD)VRBO
From $1167 per night (USD)Expedia
Deja Blu:1 Block to Beach! Tropical Oasis, Poolside Lounge, Pool & Spa by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Deja Blu by Anna Maria Life Vacation Rentals 208 Palm Ave, Anna Maria, FL 34217 What You'll Love About This Home: Locat ...
From $1167 per night (USD)Expedia
From $634 per night (USD)VRBO
Meant to Be:1 Block to Beach! North End! Pool & Spa,Loaded Game Room by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Meant to Be by Anna Maria Life Vacation Rentals 804 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About This Home ...
From $634 per night (USD)VRBO
From $1036 per night (USD)Expedia
4 Bed \/ 4 Bath with Stunning Views of Bimini Bay !
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You will love Bimini Bay Vue, its breathtaking, unobstructed 180-degree angle views of Bimini Bay are stunning. Complete ...
From $1036 per night (USD)Expedia
From $1651 per night (USD)VRBO
Luxury home with Pool and Spa, Rooftop deck, Water views, Golf cart, and Bikes!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Sweet Caroline by AMI Locals Home in Anna Maria, FL 34216 VR23-000009 Highlights • Private Pool and In-ground Spa • 2-m ...
From $1651 per night (USD)VRBO
From $2620 per night (USD)Expedia
No Tan Lines by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
The ultimate in beach front Florida island living awaits you at No Tan Lines. *Features include* * Ultimate luxury BE ...
From $2620 per night (USD)Expedia
From $664 per night (USD)VRBO
The Hammock House: Bright and modern pool home with outdoor living space
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The Hammock House, located on the North end of Anna Maria is a 3 bedroom, 3.5 bathroom spacious, contemporary home. The ...
From $664 per night (USD)VRBO
From $863 per night (USD)Expedia
H2O 360 by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Water abounds at this awesome 3 bedroom/2 bath Anna Maria Island gem with pool, hot tub and dock! *Features include* ...
From $863 per night (USD)Expedia
From $1081 per night (USD)VRBO
Anna Belle by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Slip into "island time" immediately and surround yourself with elegance and style in this amazing one-level beauty. The ...
From $1081 per night (USD)VRBO
From $1276 per night (USD)Expedia
The TipSea Turtle managed by Beach Retreats FL Anna Maria Island
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Views! Contactless entry Private heated pool & spa 3 hole mini-putt Parking for 4 Electric vehichle charger Fully Eq ...
From $1276 per night (USD)Expedia
From $893 per night (USD)VRBO
Summer Deals! - Putting Green\/Waterfront\/Dock\/\/Pool\/ Hot Tub\/Steps to Beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Check out our Summer Last Minute Deals! June 21 - 28, 2025 now $6,499/wk* plus fees and taxes June 28 - July 5, 2025 no ...
From $893 per night (USD)VRBO
From $971 per night (USD)Expedia
Sandy Beach Retreat - 3 bedroom on the beach with amazing views and private pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to Sandy Beach Retreat! You will fall in love with the beautiful beaches of Anna Maria Island as your backyard i ...
From $971 per night (USD)Expedia
From $1520 per night (USD)VRBO
Bean Point Bliss: Pool Spa Putting Green
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bean Point Bliss by Anna Maria Life Vacation Rentals 820 N Shore, Anna Maria FL 34216 What You'll Love About This Home: ...
From $1520 per night (USD)VRBO
From $508 per night (USD)Expedia
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Anna Maria Island waterfront house newly renovated. The house is located on a large 75 ft wide deep water canal an ...
From $508 per night (USD)Expedia
From $1313 per night (USD)VRBO
Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
749 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: Location! Bean Point Across the Street! 2 Min Wal ...
From $1313 per night (USD)VRBO
From $636 per night (USD)Expedia
On Point: Across Street from Bean Point Beach, Outdoor Games & Pool by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
811 Jacaranda, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1 Block to Beach & Bean Point! 4 Bedroo ...
From $636 per night (USD)Expedia
From $984 per night (USD)VRBO
The Laguna Beach: 2 Blocks to Beach, Pool, 5 Hole Put Put, Foosball, Cornhole by Anna Maria Life
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Laguna Beach by Anna Maria Life Vacation Rentals 212 Willow Ave, Anna Maria, FL 34216 What You'll Love About This H ...
From $984 per night (USD)VRBO
From $229 per night (USD)Expedia
Endless Summer- On Pine Ave, steps to beach & pier w\/ water view & dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOCATION IS EVERYTHING!! Endless Summer is a waterfront condo with amazing views and a private dock, perfectly located o ...
From $229 per night (USD)Expedia
From $1230 per night (USD)VRBO
Banyan Tree Beach House- Luxury home with private pool
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Banyan Tree Beach House!! If you think the photos are stunning, wait until you see this home in person and wa ...
From $1230 per night (USD)VRBO
From $553 per night (USD)Expedia
Island Breeze: Steps to Beach, Heated Pool & Spa, Huge Verandah by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Breeze by Anna Maria Life Vacation Rentals 119 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $553 per night (USD)Expedia
From $2449 per night (USD)VRBO
Luxury Villa with Rooftop Deck, Putting Green, and Pool\/Spa!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 8
Fine and Sandy by AMI Locals Home in Anna Maria, FL Located in the North End area of Anna Maria Island Highlights: • P ...
From $2449 per night (USD)VRBO
From $266 per night (USD)Expedia
Bayou Breeze | Amazing Waterfront Condo on Pine Ave with Dock and Water Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Amazing Waterfront Condo at the North end of Anna Maria! Tucked away off of Pine Ave just before the Historic Anna Mar ...
From $266 per night (USD)Expedia
From $1375 per night (USD)VRBO
Luxury Home with Private Pool, Putting Green, and Dock!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Yacht Sea by Anna Maria Island Accommodations Home in Anna Maria, FL Highlights • 5-minute walk from Beach • Private Po ...
From $1375 per night (USD)VRBO
From $822 per night (USD)Expedia
Anna Banana: 3 Houses to Beach! North End AMI! Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Banana by Anna Maria Life Vacation Rentals 501 North Shore, Anna Maria, FL 34216 What You'll Love About this Home: ...
From $822 per night (USD)Expedia
From $1658 per night (USD)VRBO
Bay Happy: Luxury Home with View of Tampa Bay!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Bay Happy is the perfect place for your next island getaway! This luxury property boasts breathtaking views of the bay, ...
From $1658 per night (USD)VRBO
From $196 per night (USD)Expedia
Bayou Hideaway: 2 BR, 1 BA Condominium in Anna Maria, Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great Pine Avenue location, across the street from the Anna Maria City Pier, walkable to Bayfront Park with its playgrou ...
From $196 per night (USD)Expedia
From $1293 per night (USD)VRBO
Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria - Hip Nautic
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Hip Nautic by AMI Locals Home in Anna Maria, Florida Welcome to Hip Nautic, the ultimate luxury beach retreat on Anna ...
From $1293 per night (USD)VRBO
From $759 per night (USD)Expedia
Mangrove Mojito: Canal, Pool, Hot Tub, Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous and spacious is this 4 Bedroom/3 Bath Home in a desirable north-end location, just steps to Historic Pine Avenu ...
From $759 per night (USD)Expedia
From $1286 per night (USD)VRBO
All's Well on AMI: Spacious with pool, hot tub, walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
All's Well on AMI is a brand new custom built home just steps from the gulf! This spacious property has an oversized kit ...
From $1286 per night (USD)VRBO
From $738 per night (USD)Expedia
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
New to the Vacation Rental Market and awaiting your Reviews! Only a few steps from the sugar white beaches and crystal ...
From $738 per night (USD)Expedia
From $1227 per night (USD)VRBO
Mahi Mahi:North End, Pool & Spa, Game Room, 1.5 Blocks to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Mahi Mahi by Anna Maria Life Vacation Rentals 213 Elm, Anna Maria, FL 34216 What You'll Love About This Home: Location! ...
From $1227 per night (USD)VRBO
From $632 per night (USD)Expedia
8 Palms: Gorgeous heated pool and lounge area, with putt-putt!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
8 palms is a beautiful 3 bedroom 2 bath home on the North end of Anna Maria Island. The property is newly renovated and ...
From $632 per night (USD)Expedia
From $1207 per night (USD)VRBO
Dragonfly Harbour: Spectacular Canal Front Home, Pool, Hot Tub Rooftop Deck by Anna Maria Life
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Dragonfly Harbor by Anna Maria Life Vacation Rentals 511 Loquat Dr, Anna Maria, FL 34216 What You'll Love About This Ho ...
From $1207 per night (USD)VRBO
From $1858 per night (USD)Expedia
The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The Willow Inn by Anna Maria Life Vacation Rentals 201 Willow Ave, Anna Maria, FL 34216 What You'll Love About This Hom ...
From $1858 per night (USD)Expedia
From $1641 per night (USD)VRBO
Perfect Location! Backyard Oasis with Heated Pool, Rooftop Deck - Under the Sun
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Under the Sun by AMI Locals Home in Anna Maria, FL VR22-000075 Escape to Under the Sun, a premier five-bedroom, four- ...
From $1641 per night (USD)VRBO
From $422 per night (USD)Expedia
Mykonos: Beautifully updated with heated pool, moments to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come join us at Mykonos on Anna Maria Island! This beautifully decorate, two bedroom, two bathroom home has the perfect ...
From $422 per night (USD)Expedia
From $449 per night (USD)VRBO
Eclectic North end AMI home with Private pool on Canal!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Right on the water with canal access in the back yard. Private swimming pool overlooks the water.and Ample Parking for y ...
From $449 per night (USD)VRBO
From $502 per night (USD)Expedia
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Getaway on Gladiolus Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $502 per night (USD)Expedia
From $310 per night (USD)VRBO
Coconut Bayou by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Bayou 5C! With a prime location the north side of Pine Avenue on Anna Maria Island. The Bayou 5C is the ...
From $310 per night (USD)VRBO
From $556 per night (USD)Expedia
Wave n Sea - Close to the Beach with Pool - Anna Maria Island - By Island Real E
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Wave N’Sea” is a premiere vacation home located in the city of Anna Maria on Anna Maria Island. Here you’ll find a perf ...
From $556 per night (USD)Expedia
From $892 per night (USD)VRBO
Family-Friendly Home with Pool Near Amazing Anna Maria Island Attractions!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Blue-tiful Horizons by AMI Locals Home in Anna Maria, Florida VR22-000026 Escape to Blue-tiful Horizons, a beautiful ...
From $892 per night (USD)VRBO
From $1052 per night (USD)Expedia
North Shore Beach House: Tranquil 4BR Retreat with Pool, Spa, & Walk to Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to North Shore Beach House, your serene sanctuary on the North End of Anna Maria Island. This stunning 4-bedroom, ...
From $1052 per night (USD)Expedia
From $2677 per night (USD)VRBO
Luxury Beachfront on the Sand of Gulf of Mexico
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Photos Updated January 2025! Elevator is currently not in working order. We are waiting on repairs to finish. Sunnysid ...
From $2677 per night (USD)VRBO
From $1509 per night (USD)Expedia
BeachFront 4\/3\/ Amazing Views plus hot tub
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Beach front Bliss… Enjoy Swimming or relaxing in this 4 bedroom home on the North End of Anna Maria Island. Captivating ...
From $1509 per night (USD)Expedia
From $971 per night (USD)VRBO
Mia Bella walk to beach on canal 2 king suites AMI private dock\/pool villa
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Create unforgettable memories at Mia Bella located on Hammock Road, just north of Pine Avenue, in a *premier deep water ...
From $971 per night (USD)VRBO
From $3319 per night (USD)Expedia
Luxury Home with Pathway to the Beach! Secluded Pool and Spa!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Coastal Couture by AMI Locals Home in Anna Maria, Florida VR21-000085 Welcome to Coastal Couture! This luxurious mul ...
From $3319 per night (USD)Expedia
From $510 per night (USD)VRBO
Hav'Anna Holiday: 2 Blocks to Beach! North End! Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Hav'Anna Holiday by Anna Maria Life Vacation Rentals 211 Periwinkle, Anna Maria, FL 34217 What You'll Love About This H ...
From $510 per night (USD)VRBO
From $1377 per night (USD)Expedia
Park n Chill: North End, Steps to Beach, West of Gulf, Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Park n Chill by Anna Maria Life Vacation Rentals 117 Park Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1377 per night (USD)Expedia
From $1224 per night (USD)VRBO
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
322 Tarpon Ave, Anna Maria FL, 34216 What You'll Love About This Home: Location! On a Canal. 4 Blocks to the Beach! 2 B ...
From $1224 per night (USD)VRBO
From $1258 per night (USD)Expedia
150 Feet to the Beach! Large Beach Home with Heated Pool! - Sunset Paradise
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Sunset Paradise by Anna Maria Vacations 109 Pine Avenue Anna Maria, FL 34216 Get ready to live your dream beach vacatio ...
From $1258 per night (USD)Expedia
From $1079 per night (USD)VRBO
Beach a la Mode | Luxury Canal Front Home on AMI w\/ Private Pool & Spa
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 8
Welcome to your dream vacation home on Anna Maria Island - a luxurious 5-bedroom, 4.5-bathroom canal front retreat that ...
From $1079 per night (USD)VRBO
From $1567 per night (USD)Expedia
Salty Sister: Stunning Beachfront Vacation Home with Heated Pool, Steps from Anna Maria Island Beach
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Salty Sister, the pinnacle of coastal luxury on Anna Maria Island, where the crystal-clear waters of the Gulf ...
From $1567 per night (USD)Expedia
From $584 per night (USD)VRBO
Heated Pool, Gas Grill, 1 Minute Walk to Beach! Updated Throughout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sugar Plum Beach West by Anna Maria Vacations Home in Anna Maria, FL 34216 VRC18-000058 Welcome to Sugar Plum Beach Wes ...
From $584 per night (USD)VRBO
From $359 per night (USD)Expedia
Short stays available! Located on North End of Island.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #4 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #4, a ...
From $359 per night (USD)Expedia
From $971 per night (USD)VRBO
Canal Front Home with Private Dock, Saltwater Pool, Kayaks - Magnolia Breeze
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Magnolia Breeze by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000454 Escape to the serenity of Magnolia ...
From $971 per night (USD)VRBO
From $479 per night (USD)Expedia
Dog friendly and located in the heart of Anna Maria! Near the beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Hideaway by Anna Maria Island Locals Home in Anna Maria, FL Highlights - Nestled in the heart of Anna Maria Island ...
From $479 per night (USD)Expedia
From $1509 per night (USD)VRBO
Large Private Beach Home. Private Pool and Spa, Outdoor Lighting
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Southern Exposure by Anna Maria Vacations Home in Anna Maria, FL VRC16-000065 Highlights • Less than a 10-minute walk ...
From $1509 per night (USD)VRBO
From $644 per night (USD)Expedia
Charming cottage located close to beach - private heated pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Tree Top Bungalow by Anna Maria Vacations Home in Anna Maria, Fl. 34216 VR16-000079 Tree Top Bungalow combines the best ...
From $644 per night (USD)Expedia
From $766 per night (USD)VRBO
Close to the Beach with Pool n Ping Pong Table! Pelican Villa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Pelican Villa by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000467 Welcome to Pelican Villa, an elevated th ...
From $766 per night (USD)VRBO
From $861 per night (USD)Expedia
Single Level Beach Home, 5 Minutes to the Sand! Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sunshine Reef by Anna Maria Vacations Home in Anna Maria, Fl 34216 VR16-000425 Experience the perfect family getaway at ...
From $861 per night (USD)Expedia
From $1233 per night (USD)VRBO
Elevated Beach Home, 3 Minutes to the Sand! Private Heated Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Las Palmas by Anna Maria Vacations Anna Maria, Fl. 34216 VR16-000470 Welcome to Las Palmas, an exquisite vacation home ...
From $1233 per night (USD)VRBO
From $1160 per night (USD)Expedia
Canal Front Home with Dock, Saltwater Pool, Ping Pong - Ama Maria
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ama Maria by Anna Maria Vacations Home in Anna Maria, FL VR16-000113 Welcome to Ama Maria! This three-bedroom and two ...
From $1160 per night (USD)Expedia
From $383 per night (USD)VRBO
Short stays available! 5-7 Minute Walk to the Gulf Beaches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southern Breeze #1 by Anna Maria Vacations Duplex in Anna Maria, FL 34216 VR16-000199 Welcome to Southern Breeze #1, a ...
From $383 per night (USD)VRBO
From $590 per night (USD)Expedia
Private Home with Pool, Outdoor Dining Area with BBQ - Whispering Whale Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Whispering Whale Retreat by Anna Maria Vacations Home in Anna Maria, Fl 34216 VR16-000195 Welcome to Whispering Whale ...
From $590 per night (USD)Expedia
From $1054 per night (USD)VRBO
Private Home with Private Pool, Outdoor Spa, Game Room, Private Grill, and More!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Antigua Bay by Anna Maria Vacations Home in Anna Maria, FL 34216 VR16-000450 Antigua Bay is a beautiful dog-friendly ho ...
From $1054 per night (USD)VRBO
From $631 per night (USD)Expedia
Coconut Cove: *Canalfront *Pet-friendly *Putt-putt *Pool *Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Photos Updated March 2025! Escape to the secluded paradise of Coconut Cove on Anna Maria Island, a 3-bedroom, 3-bathroo ...
From $631 per night (USD)Expedia
From $1107 per night (USD)VRBO
Elevated North-End Home Near the Beach!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunshine State of Mind by AMI Locals Home in Anna Maria, FL Experience panoramic sunset views, gulf breezes, and the sm ...
From $1107 per night (USD)VRBO
From $945 per night (USD)Expedia
Ocean Minded by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your dream beach retreat - Ocean Minded - where barefoot luxury meets effortless island living. *Features in ...
From $945 per night (USD)Expedia
From $723 per night (USD)VRBO
Limelight by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Limelight, a stunning 3 bedroom vacation home perfectly situated on the picturesque north end of Anna Maria, ju ...
From $723 per night (USD)VRBO
From $1376 per night (USD)Expedia
Manatee Lookout: Canal Front, Pool, Spa, Dock, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Manatee Lookout by Anna Maria Life Vacation Rentals 214 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1376 per night (USD)Expedia
From $1103 per night (USD)VRBO
Coconut Hut: Pool & Spa, Pool Table, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Coconut Hut by Anna Maria Life Vacation Rentals 213 Coconut Ave, Anna Maria, FL 34217 What You'll Love About This Home: ...
From $1103 per night (USD)VRBO
From $242 per night (USD)Expedia
Gone Coastal: *3 mins to beach *Pet-Friendly *Budget-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Gone Coastal, a budget-friendly retreat perfect for your vacation. This affordable, 2-bedroom, 2-bathroom hom ...
From $242 per night (USD)Expedia
From $1215 per night (USD)VRBO
Sentimental Sunset: Pool & Spa, Near Bean Point & Pine! by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Sentimental Sunset by Anna Maria Life Vacation Rentals 755 Jacaranda Rd, Anna Maria, FL 34216 What You'll Love About Th ...
From $1215 per night (USD)VRBO
From $890 per night (USD)Expedia
Ready to host after the storms! Private Home. Large Heated Pool. Steps to beach.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Anna Maria Chateau is a well appointed coastal home located just a quick walk from the beach/Bean Point. Walk to the loc ...
From $890 per night (USD)Expedia
From $522 per night (USD)VRBO
Dock Holiday: On Canal, Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Dock Holiday by Anna Maria Life Vacation Rentals 235 Chilson Ave, Anna Maria, FL 34216 What You'll Love About This Home ...
From $522 per night (USD)VRBO
From $1466 per night (USD)Expedia
Tropical gem near beach with amazing Gulf view, pool, spa, game room & roof deck
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Tropical Gulf View Estate Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $1466 per night (USD)Expedia
From $791 per night (USD)VRBO
Periwinkle Getaway: 2 Blocks to the Beach, Private Pool by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
207 Periwinkle Plaza, Anna Maria, FL 34216 What You'll Love About This Home: Location! 1.5 Blocks to the Beach! 3 Bedroo ...
From $791 per night (USD)VRBO
From $624 per night (USD)Expedia
Coral Cove: Walk to the Beach! Heated pool! Prime North End!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
*Features include* * Prime north end location! Bean Point! * Walk to the beach! * Private, saltwater heated pool * Larg ...
From $624 per night (USD)Expedia
From $1204 per night (USD)VRBO
Canal front with Dock and Pool -Honeywood House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Honeywood House by Anna Maria Island Accommodations Home in Anna Maria, Florida Relaxation and adventure await you at ...
From $1204 per night (USD)VRBO
From $665 per night (USD)Expedia
Welcome to Gulf Shore Cottage!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gulf Shore Cottage by Anna Maria Island Accommodations Cottage in Anna Maria, Florida VR16-000101 Your dream beach vac ...
From $665 per night (USD)Expedia
From $1243 per night (USD)VRBO
Salty Sunsets, full gulf views from rooftop deck, gorgeous pool\/spa
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Salty Sunsets on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy ...
From $1243 per night (USD)VRBO
From $1311 per night (USD)Expedia
La Hacienda: Dock on Canal, Full Game Room, Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
La Hacienda by Anna Maria Life Vacation Rentals 103 Los Cedros, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1311 per night (USD)Expedia
From $515 per night (USD)VRBO
Duplex for multiple groups and pool - Hang 12
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Hang 12 by Anna Maria Island Accommodations Whole Duplex in Holmes Beach, Florida Hang out with your family and frien ...
From $515 per night (USD)VRBO
From $471 per night (USD)Expedia
The Wee Cottage | House in Anna Maria
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
The Wee Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $471 per night (USD)Expedia
From $548 per night (USD)VRBO
Anna Maria Aloha – Beach Block Cottage, Steps to Gulf, Outdoor Living, Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Anna Maria Aloha! On Anna Maria Island (Anna Maria, Florida) After sustaining hurricane damage, this charmin ...
From $548 per night (USD)VRBO
From $401 per night (USD)Expedia
WE ARE BACK! Pictures to come. Charming canal cottage, 4 minute stroll to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Javea is completely redone from damage from Hurricane Helene. We will update the pictures soon. We are a ground l ...
From $401 per night (USD)Expedia
From $515 per night (USD)VRBO
Steps to Beach - Bean Point Residence Unit A by SeaBreeze Vacation
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers conv ...
From $515 per night (USD)VRBO
From $458 per night (USD)Expedia
Steps to Beach - Bean Point Residence Unit B by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
For our beachgoer guests, the beach entrance to Anna Maria's sandy, white beaches are approximately 40 steps away. Bean ...
From $458 per night (USD)Expedia
From $1081 per night (USD)VRBO
Newly Renovated Canal Front Home. Just Steps to Bay!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Highlights • Canal front with dock • 9-minute walk to the beach • Private pool and hot tub • Putting green • Game room ...
From $1081 per night (USD)VRBO
From $1025 per night (USD)Expedia
Perfect Family Waterfront Home! Stunning Views! Near Local Attractions - Seaside
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Seaside by Anna Maria Vacations VR16-000432 Welcome to Seaside! This three-bedroom and two-and-a-half bath waterfront h ...
From $1025 per night (USD)Expedia
From $1173 per night (USD)VRBO
Fancy Flamingo: Canal Front, Dock, Heated Pool & Spa by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Fancy Flamingo by Anna Maria Life Vacation Rentals 319 Hardin, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1173 per night (USD)VRBO
From $456 per night (USD)Expedia
Bay Breeze Bungalow: Canalfront family home with dock and pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to Bay Breeze Bungalow – your idyllic getaway nestled in the heart of Anna Maria Island! This charming 3-bedroom ...
From $456 per night (USD)Expedia
From $628 per night (USD)VRBO
AMI Outpost - 3 Bed 2 Bath Elevated Home - by Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming elevated villa in the heart of Anna Maria with private heated pool and fenced yard. Short walk to City Pier and ...
From $628 per night (USD)VRBO
Click For PricingExpedia
Island Memories by SeaBreeze Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is where you will make Island Memories! Situated less than a 2 minute walk to the white, sandy beaches of Anna Mari ...
Click For PricingExpedia
From $928 per night (USD)VRBO
Sea Star by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ideally located just steps from the beach, Sea Star offers a unique 3 bedroom vacation home with carriage house for a pe ...
From $928 per night (USD)VRBO
From $768 per night (USD)Expedia
EV Charger, Coastal Serenity by SeaBreeze Vacation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Coastal Serenity has a rooftop deck, private pool and spa, a ping pong table, and an EV Charger! This single family home ...
From $768 per night (USD)Expedia
From $2112 per night (USD)VRBO
Brand New home with Incredible Rooftop Deck and Pool! - Just Breathe
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Just Breathe by AMI Locals Home in Anna Maria, FL 34216 Welcome to Just Breathe, a brand-new construction right across ...
From $2112 per night (USD)VRBO
From $1320 per night (USD)Expedia
Canal Walk: Tiki Bar, Mini Golf, Pool & Spa On Canal by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Canal Walk by Anna Maria Life Vacation Rentals 223 Oak Ave, Anna Maria FL, 34216 What You'll Love About This Home: Loca ...
From $1320 per night (USD)Expedia