Anna Maria Rentals
From $458 per night (USD)VRBO
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $458 per night (USD)VRBO
From $662 per night (USD)Expedia
Sassy Seagull -Classic beach cottage, moments from the sand, beautiful pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $662 per night (USD)Expedia
From $485 per night (USD)VRBO
Anna Maria Beach Cottage 107A Pool, bikes, beach gear, moments from the sand!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14- OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered duri ...
From $485 per night (USD)VRBO
From $494 per night (USD)Expedia
Charming beach cottage close to the beach with Pool, Bikes, Beach gear and Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $494 per night (USD)Expedia
From $472 per night (USD)VRBO
Anna Maria Updated Studio moments from the sand w/ Pool, Beach Gear & Bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $472 per night (USD)VRBO
From $581 per night (USD)Expedia
Charming Cottage with modern amenities close to beach w/ pool, beach gear, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $581 per night (USD)Expedia
From $835 per night (USD)VRBO
Flirty Flamingo Cottage Updated beach cottage, moments from the sand, w/pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $835 per night (USD)VRBO
From $494 per night (USD)Expedia
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PLEASE NOTE THE POOL WILL BE CLOSED SEPTEMBER 14 - OCTOBER 5, 2026 FOR RESURFACING. Special rates are being offered dur ...
From $494 per night (USD)Expedia
From $8594 per night (USD)VRBO
Charming cottage with heated pool, tropical landscaping in prime location.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Starfish Cottage has been recently renovated while maintaining all the charm of an old Florida Key West style bungal ...
From $8594 per night (USD)VRBO
From $1792 per night (USD)Expedia
Impressive Luxury Home steps to the Beach! Great Pool and Spa! - Grande Haven
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
Grande Haven by AMI Locals VR18-000049 *Grande Haven is currently undergoing major renovations, bringing fresh upgrade ...
From $1792 per night (USD)Expedia
From $311 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 $311 per night (USD)VRBO
From $499 per night (USD)Expedia
Beach Pearl - Private Pool Home - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just a short stroll from Gulf of Mexico beaches, Anna Maria vacation rental “Beach Pearl” offers a luxurious getaway exp ...
From $499 per night (USD)Expedia
From $1316 per night (USD)VRBO
Tern Key - Luxury Canal-Front Home w/ Heated Pool, Spa, Dock & Near Bean Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Tern Key! On Anna Maria Island (Anna Maria, FL) The Space Tern Key is a home that feels both artful and effo ...
From $1316 per night (USD)VRBO
From $1007 per night (USD)Expedia
Modern Beach House with excellent location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Direct Beach Access, fully renovated beach house. Brand new pool renovated in 2026, Main floor master suite that walks o ...
From $1007 per night (USD)Expedia
From $1062 per night (USD)VRBO
Pink Palm: Dog-friendly, 6-bedroom, 3-min walk to beach!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Pink Palm is one of the most impressive vacation rentals on Anna Maria Island! The home is located just a half a block a ...
From $1062 per night (USD)VRBO
From $1424 per night (USD)Expedia
Still Waters Beach House- A north end tropical getaway.
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Still Waters Beach House! Come rest and be refreshed in one of the most family friendly and spacious (3600+ S ...
From $1424 per night (USD)Expedia
From $558 per night (USD)VRBO
BEST LOCATION! NORTH END OF ANNA MARIA, FL , STEPS TO BEACH & DINING , UNIT B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Green Jacaranda Unit B (Upstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach less ...
From $558 per night (USD)VRBO
From $537 per night (USD)Expedia
Fun in the Sun Gulf front, steps to the sand, 4-bed with spectacular views!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Recently Updated Vintage Island Beach Front home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in t ...
From $537 per night (USD)Expedia
From $660 per night (USD)VRBO
Anna Maria Escape! Pool, Spa, and Canal Views - Our Tern
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tern by Anna Maria Island Accommodations VR22-000023 Welcome to Our Tern, a gorgeous canal front vacation home on ...
From $660 per night (USD)VRBO
From $553 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 $553 per night (USD)VRBO
From $1450 per night (USD)VRBO
Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak, SUPs & MORE
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to the Rum Cove Experience! This magical home is a one-of-a-kind oasis 🌴 on a one-of-a-kind island located ri ...
From $1450 per night (USD)VRBO
From $582 per night (USD)Expedia
Over the Moon - By Island Real Estate Vacations
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
“Over the Moon” located on the North end of Anna Maria is an adorable 3 bedroom, 2 bathroom cottage that spaciously acco ...
From $582 per night (USD)Expedia
From $808 per night (USD)VRBO
Banyan Beach: Steps to Beach, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Banyan Beach by Anna Maria Life Vacation Rentals 104 Beach Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $808 per night (USD)VRBO
From $1499 per night (USD)Expedia
Snook Lookout: Canal Home, Pool, Game Room, Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Snook Lookout by Anna Maria Life Vacation Rentals 211 Oak Ave, Anna Maria, FL 34216 What You'll Love About This Home: L ...
From $1499 per night (USD)Expedia
From $1067 per night (USD)VRBO
Luxury 4-Bedroom Home Near Beach with Pool and Spa at Under The Sea, Anna Maria!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Under The Sea by AMI Locals VR17-000055 Welcome to Under the Sea, a luxurious four bedroom, four and a half bath home ...
From $1067 per night (USD)VRBO
From $1127 per night (USD)Expedia
Stunning 5 Bedroom Luxury Home, Pool and Spa, Beach Views!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Coastal Queen by AMI Locals VR18-000091 Welcome to Coastal Queen, a warm and inviting luxury vacation home nestled on ...
From $1127 per night (USD)Expedia
From $1876 per night (USD)VRBO
Gulfview Estate: Beachfront luxury home with sweeping Gulf views
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Gulfview Estate, your exquisite beachfront retreat where luxury meets tranquility. This stunning 5-bedroom, 4 ...
From $1876 per night (USD)VRBO
From $261 per night (USD)Expedia
\"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 $261 per night (USD)Expedia
From $891 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 $891 per night (USD)VRBO
From $565 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 $565 per night (USD)Expedia
From $463 per night (USD)VRBO
Beach N Bay 206 by Duncan Real Estate
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Beach N Bay 206! A honeymooners delight or a couple’s retreat! Enjoy a romantic getaway! Don't miss your ch ...
From $463 per night (USD)VRBO
From $620 per night (USD)Expedia
The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Only a few steps from the sugar white beaches and crystal waters of the gulf, this long-time island family home is now b ...
From $620 per night (USD)Expedia
From $895 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 $895 per night (USD)VRBO
From $923 per night (USD)Expedia
4 Beds 4.5 Bath with Pool 3 Blocks to Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
You won't be disappointed with this home! This 4 bedroom, 4.5 bathroom home is located in the heart on ANNA MARIA ISLAND ...
From $923 per night (USD)Expedia
From $773 per night (USD)VRBO
4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Seaside Maison - a beautifully appointed 4-bedroom, 4.5-bath island retreat on the north end of Anna Maria Is ...
From $773 per night (USD)VRBO
From $991 per night (USD)Expedia
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 $991 per night (USD)Expedia
From $748 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 $748 per night (USD)VRBO
From $848 per night (USD)Expedia
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 $848 per night (USD)Expedia
From $526 per night (USD)VRBO
Back To Blue: Amazing Bean Point Location, Resort Style Backyard with Pool by Anna Maria Life
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
Back to Blue by Anna Maria Life Vacation Rentals 850 North Shore Drive, Anna Maria, FL 34216 What You'll Love About Thi ...
From $526 per night (USD)VRBO
From $742 per night (USD)Expedia
Dragonfly Harbour: Spectacular Canal Front Home, Pool, Hot Tub Rooftop Deck by Anna Maria Life
- Bedrooms:
- 4
- 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 $742 per night (USD)Expedia
From $384 per night (USD)VRBO
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seeking a private piece of Anna Maria Island charm? This Anna Maria rental is ideal for a small family, a romantic escap ...
From $384 per night (USD)VRBO
From $814 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 $814 per night (USD)Expedia
From $812 per night (USD)VRBO
Luxury AMI Home with Pool, Rooftop Deck, and Putting Green! 2 Blocks to Beach!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Tahiti Bay by AMI Locals VR16-000466 Welcome to Tahiti Bay, a luxury beach vacation home just a short walk from Anna M ...
From $812 per night (USD)VRBO
From $1381 per night (USD)Expedia
The Willow Inn: Huge Pool, Game Room, One Block to Beach by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- 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 $1381 per night (USD)Expedia
From $629 per night (USD)VRBO
Bayside Bliss by Duncan Real Estate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Bayside Bliss which is a fully remodeled three-bedroom/three-bathroom, ground level cottage north of Pine Ave ...
From $629 per night (USD)VRBO
From $564 per night (USD)Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Purple Alamanda Unit A (Downstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach les ...
From $564 per night (USD)Expedia
From $432 per night (USD)VRBO
Sea Spray 5: *Heated Pool *Steps to beach *Close to shops and dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
**Photos Updated April 2025** The Sea Spray Cottages are an adorable group of Units located in the North End of Anna Mar ...
From $432 per night (USD)VRBO
From $791 per night (USD)Expedia
Under the Sun! Rooftop Deck, Pool and Spa!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Under the Sun by AMI Locals VR22-000075 Welcome to Under the Sun! This five bedroom, four and a half bath Anna Maria ...
From $791 per night (USD)Expedia
From $1102 per night (USD)VRBO
Golf Cart, Bimini Cove by SeaBreeze Vacation
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid ...
From $1102 per night (USD)VRBO
From $489 per night (USD)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 ...
From $489 per night (USD)Expedia
From $1572 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 $1572 per night (USD)VRBO
From $814 per night (USD)Expedia
A Bay From It All: Private backyard oasis, steps to Bay, Bean Point
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
***Photos updated May 2025*** Leave the stress of everyday life and get "A Bay From it All"! This amazing 3 bedroom / 3 ...
From $814 per night (USD)Expedia
From $666 per night (USD)VRBO
Jungalow Bay by Beach Boutique Rentals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian para ...
From $666 per night (USD)VRBO
From $435 per night (USD)Expedia
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Open for business in 2025! We are ready to host you and your family!!MI Oasis Getaway is a true oasis on both the outsi ...
From $435 per night (USD)Expedia
From $5726 per night (USD)VRBO
The Rod and Reel Resort
- Bedrooms:
- 8
- Bathrooms:
- 11
- Sleeps:
- 30
Welcome to the new and luxurious Rod and Reel Resort. We are pleased to offer our guests the finest and most inclusive e ...
From $5726 per night (USD)VRBO
From $328 per night (USD)Expedia
Ideal Location, Stunning Villa! Close to beach, beach gear provided!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seeking a private piece of Anna Maria Island charm? This Anna Maria rental is ideal for a small family, a romantic escap ...
From $328 per night (USD)Expedia
From $734 per night (USD)VRBO
Luxury Home with Pool and Dock for Fishing!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Pelican’s Nest by AMI Locals VR20-000006 Welcome to Pelican’s Nest, a breathtaking three bedroom, three bath canal-fr ...
From $734 per night (USD)VRBO
From $1297 per night (USD)VRBO
Spectacular Beachfront House with Pool
- Bedrooms:
- 4
- 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 $1297 per night (USD)VRBO
From $409 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 $409 per night (USD)VRBO
From $684 per night (USD)Expedia
Mykonos: Beautifully updated with heated pool, moments to the Gulf
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come join us at Mykonos on Anna Maria Island! This beautifully decorate, two bedroom, two bathroom home has the perfect ...
From $684 per night (USD)Expedia
From $274 per night (USD)VRBO
Pine Ave Best Location on Island! Steps from the water & island favorites.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Steps from the Beach & Pine Avenue Dining Experience the best of Anna Maria Island from this beautifully furnished grou ...
From $274 per night (USD)VRBO
From $1290 per night (USD)VRBO
North end canal front home ,tiki hut, dock, pool, spa, beaches....
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Single family quiet vacation home on Lake La Vista has it all... Incredible view with Roser Church across the canal. Thi ...
From $1290 per night (USD)VRBO
From $2097 per night (USD)VRBO
Bay Happy: Luxury Home with View of Tampa Bay!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bay Happy is the perfect place for your next island getaway! This luxury property boasts breathtaking views of the bay, ...
From $2097 per night (USD)VRBO
From $560 per night (USD)Expedia
Everything inside is new and beachy! 2 blocks to Bean Point Beach! DOGS ALLOWED
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Cozy Coastal Cottage – 2 Blocks to Bean Point | Heated Pool | DOG-Friendly - ( 2 Dogs MAX up to 50 lbs ) Inside, y ...
From $560 per night (USD)Expedia
From $695 per night (USD)VRBO
Island Time: AMI North End, Pool, Close to City Pier & Pine Ave by Anna Maria Life Vacation Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Island Time by Anna Maria Life Vacation Rentals 426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $695 per night (USD)VRBO
From $803 per night (USD)VRBO
SOUTH CAY, 3-Min Walk to Gulf Beach, Large Pool, 2 Master BR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
LARGE Heated Pool, 2 MB Suites. "South Cay" is very close to Gulf Beach (look us up). Only 11 houses to Gulf beach - clo ...
From $803 per night (USD)VRBO
From $777 per night (USD)VRBO
LABOR DAY SPECIALS ,BEACHFRONT, 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 $777 per night (USD)VRBO
From $990 per night (USD)Expedia
Luxury Beach Retreat with Rooftop Deck and Pool in Anna Maria! - Hip Nautic
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Hip Nautic by AMI Locals VR22-000090 Welcome to Hip Nautic, a luxury four bedroom, four and a half bath beach retreat ...
From $990 per night (USD)Expedia
From $636 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 $636 per night (USD)VRBO
From $229 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 $229 per night (USD)Expedia
From $962 per night (USD)VRBO
Sirenia By The Sea -Waterfront/Dock/Pool/ Hot Tub/Putting/ Beach AMIHomeRental
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Recently Added in 2025 - outdoor cabana over dining table - outdoor kitchen with bbq grill and wine fridge - new front y ...
From $962 per night (USD)VRBO
From $370 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 $370 per night (USD)Expedia
From $1388 per night (USD)VRBO
La Grande Maison - 4 Bed / 4 Bath Luxury Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Make your next vacation one you will never forget by booking La Grande Maison. With plenty of room for the entire family ...
From $1388 per night (USD)VRBO
From $756 per night (USD)Expedia
H2O Bungalow by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
H2O Bungalow is a 3 bed, 3 bath stunning vacation home that is unique and unlike any others. *Features include* * Pr ...
From $756 per night (USD)Expedia
From $512 per night (USD)VRBO
My Mistress by Beach Boutique Rentals
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 3 bedroom/3 bath ground level canal home in Anna Maria is a hidden gem and walkable to all the best spots in Anna M ...
From $512 per night (USD)VRBO
From $1103 per night (USD)Expedia
Willow Walk: 3 Homes to Beach! West of Gulf Dr, Pool, Poolside Lounge Area by Anna Maria Life
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Willow Walk by Anna Maria Life Vacation Rentals 110 Willow Ave, Anna Maria, FL 34216 What You'll Love About This Home: ...
From $1103 per night (USD)Expedia
From $741 per night (USD)VRBO
Anna Maria Gem! Pool, Canal Views and Style!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Surf Side by AMI Locals VR22-000089 Welcome to Surf Side, a vibrant island retreat located in the heart of Anna Mar ...
From $741 per night (USD)VRBO
From $654 per night (USD)Expedia
Sand Trap by Beach Boutique Rentals
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool and mini ...
From $654 per night (USD)Expedia
From $551 per night (USD)VRBO
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 $551 per night (USD)VRBO
From $507 per night (USD)Expedia
Beachology: 1 Block to Bean Point Beach, Pool, Game Room by Anna Maria Life Vacation Rentals
- Bedrooms:
- 3
- 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 $507 per night (USD)Expedia
From $533 per night (USD)VRBO
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 $533 per night (USD)VRBO
From $311 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 $311 per night (USD)Expedia
From $385 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 $385 per night (USD)VRBO
From $232 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 $232 per night (USD)Expedia
From $1103 per night (USD)VRBO
Banyan Tree Beach House- Luxury home with private pool, spa and rooftop
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Banyan Tree Beach House 108 Park Ave, Anna Maria, FL 34216 What you will love about this property: • 3rd house from the ...
From $1103 per night (USD)VRBO
From $1746 per night (USD)Expedia
Luxury Villa with Rooftop Deck, Putting Green, and Pool/Spa!
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 8
Fine and Sandy by AMI Locals VR22-000094 Welcome to Fine and Sandy, a grand seven-bedroom, seven-bath luxury beach ho ...
From $1746 per night (USD)Expedia
From $495 per night (USD)VRBO
Pet-Friendly Retreat with Pool and Hot Tub Near the Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Mangoes on Magnolia by Anna Maria Island Accommodations VR16-000100 Welcome to Mangoes on Magnolia, a three-bedroom, t ...
From $495 per night (USD)VRBO
From $706 per night (USD)Expedia
Shady Mango by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Shady Mango! An inviting ground-level vacation home just three blocks from the beach! With two bedrooms and t ...
From $706 per night (USD)Expedia
From $714 per night (USD)VRBO
Sandy Beach Retreat - 3 bedroom on the beach with amazing views and private pool
- Bedrooms:
- 2
- 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 $714 per night (USD)VRBO
From $1554 per night (USD)Expedia
Bikini Bottom: 5 Hole Mini Golft, Games,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 $1554 per night (USD)Expedia
From $745 per night (USD)VRBO
Maritime Memories by Duncan Real Estate
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the newly renovated and updated Maritime Memories! This north-end 3 bedroom plus den, 2 bath pool home is wa ...
From $745 per night (USD)VRBO
From $1090 per night (USD)Expedia
Bean Point Bliss: Pool Spa Putting Green by Anna Maria Life Vacation Rentals
- Bedrooms:
- 4
- 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 $1090 per night (USD)Expedia
From $1073 per night (USD)VRBO
The Hammock House: Bright and modern pool home with outdoor living space
- Bedrooms:
- 3
- 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 $1073 per night (USD)VRBO
From $492 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, whirlpool spa and dock! *Features incl ...
From $492 per night (USD)Expedia
From $857 per night (USD)VRBO
Beachview Retreat: Steps to the beach, Gulf views!
- 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 $857 per night (USD)VRBO
From $301 per night (USD)Expedia
Dog-Friendly 4 Mins to the Beach and 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 VR16-000529 Welcome to A ...
From $301 per night (USD)Expedia
From $597 per night (USD)VRBO
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Place in Paradise Unit A by Anna Maria Island Accommodations Duplex in Anna Maria, Florida VR16-000529 Welcome to A ...
From $597 per night (USD)VRBO
From $701 per night (USD)Expedia
Perfect Island Location! Heated pool and plenty of room for the entire family
- 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 $701 per night (USD)Expedia
From $1922 per night (USD)VRBO
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 beachfron ...
From $1922 per night (USD)VRBO
From $766 per night (USD)Expedia
Sea Jay: Canal front with dock, heated pool, lanai w/outdoor kitchen
- 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 $766 per night (USD)Expedia