Anna Maria, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Anna Maria, Florida on RentalSaver.com!

Anna Maria Rentals

From $930 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 $930 per night (USD)
VRBO
From $920 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 $920 per night (USD)
Expedia
From $961 per night (USD)
VRBO
4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
You won't be disappointed with this brand home! This home has 4 bedrooms each with an en-suite washroom, home is located ...
From $961 per night (USD)
VRBO
From $982 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 $982 per night (USD)
Expedia
From $983 per night (USD)
VRBO
Mainsail Beach Inn 3 Bedroom Beach Facing Unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...
From $983 per night (USD)
VRBO
From $843 per night (USD)
Expedia
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 $843 per night (USD)
Expedia
From $919 per night (USD)
VRBO
Mainsail Beach Inn 3 Bedroom Beach Front Unit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...
From $919 per night (USD)
VRBO
From $747 per night (USD)
Expedia
Mainsail Beach Inn 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The stunning newly rennovated interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The ...
From $747 per night (USD)
Expedia
From $983 per night (USD)
VRBO
Mainsail Beach Inn 3 Bedroom Beach Front Unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our spacious three bedroom beachfront retreats offer up to 1,627 square feet of fully furnished living space, perfect fo ...
From $983 per night (USD)
VRBO
From $709 per night (USD)
Expedia
Mainsail Beach Inn 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The stunning interiors in your private Holmes Beach vacation rental are elegant, fresh and bright. The two bedroom, 2 ba ...
From $709 per night (USD)
Expedia
From $941 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 $941 per night (USD)
VRBO
From $880 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 $880 per night (USD)
Expedia
From $376 per night (USD)
VRBO
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 $376 per night (USD)
VRBO
From $638 per night (USD)
Expedia
Stay at Spring Haven a Anna Maria Family Rental with Pool Near Beach & Pine Ave
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spring Haven by AMI Locals Home in Anna Maria, Florida VR18-000154 Experience the perfect family vacation at Spring ...
From $638 per night (USD)
Expedia
From $640 per night (USD)
VRBO
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 $640 per night (USD)
VRBO
From $1219 per night (USD)
Expedia
Luxury Anna Maria Island Home with Pool, Rooftop Deck, and Putting Green! Scenic
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Tahiti Bay by AMI Locals Anna Maria Island Home with Pool, Rooftop Deck, and Scenic Views 215 Magnolia Ave, Anna Maria ...
From $1219 per night (USD)
Expedia
From $278 per night (USD)
VRBO
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 $278 per night (USD)
VRBO
From $546 per night (USD)
Expedia
Pristine Anna Maria Island Beachfront Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Looking to experience Old World Florida charm with a modern twist, "The Sandy Turtle" - Gulf Place Condominium #D15 on A ...
From $546 per night (USD)
Expedia
From $1461 per night (USD)
VRBO
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 $1461 per night (USD)
VRBO
From $494 per night (USD)
Expedia
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Location!!! North end of Anna Maria Island . Steps to the Bean Point Beach and everything you need for your perfect Anna ...
From $494 per night (USD)
Expedia
From $415 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 $415 per night (USD)
VRBO
From $1240 per night (USD)
Expedia
Under the Sun! Rooftop Deck + Pool & Spa!
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Under the Sun by AMI Locals Anna Maria Island Luxury Home with Rooftop Deck and Private Pool VR22-000075 Welcome to ...
From $1240 per night (USD)
Expedia
From $869 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 $869 per night (USD)
VRBO
From $175 per night (USD)
Expedia
Blue Bayou: Dog Friendly Home - 5 Houses to Beach by Anna Maria Life Vacation Rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Blue Bayou by Anna Maria Life Vacation Rentals 201 76th St. West Unit A, Holmes Beach, FL 34217 What You'll Love About ...
From $175 per night (USD)
Expedia
From $341 per night (USD)
VRBO
Beautiful Condo with Beach views! Rest and Relaxation await!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Water’s Edge 205 by AMI Locals 5808 Gulf Drive Unit 205, Holmes Beach, Florida 34217 VRC21-000026 Experience the ultim ...
From $341 per night (USD)
VRBO
From $601 per night (USD)
Expedia
Salty C Cottage Spectacular canal front home with pool and hot tub!
Bedrooms:
3
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 $601 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $272 per night (USD)
VRBO
From $475 per night (USD)
VRBO
Cozy 'Day' Side Cottage with Heated Pool Pet Friendly No size restrictions
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
VRC# 19-000218 Cozy 'Day' Side Cottage is located in Holmes Beach on Anna Maria Island. It offers 2 bedrooms and 1 1/ ...
From $475 per night (USD)
VRBO
From $1471 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 $1471 per night (USD)
VRBO
From $1024 per night (USD)
Expedia
1 Block to the Beach - LARGE Private Pool - Newly Renovated 6 Bdrm Luxury House
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Holmes Beach House For Rent - Luxury Vacation Rental on Anna Maria Island, Florida *All New Flooring, New Bathrooms (3 ...
From $1024 per night (USD)
Expedia
From $558 per night (USD)
VRBO
Beach Time AMI! Pet Friendly Home with Pool, Hot Tub and Walk to Beach
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Beach Time AMI by AMI Locals 312 65th St, Holmes Beach, FL VRC19-000030 Welcome to Beach Time AMI, a five bedroom, ...
From $558 per night (USD)
VRBO
From $499 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 $499 per night (USD)
Expedia
From $624 per night (USD)
VRBO
Jungalow Bay by Beach Boutique Rentals
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Jungalow Bay. Your Anna Maria Island adventure awaits you in this unique, modern Bohemian and Polynesian para ...
From $624 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $262 per night (USD)
VRBO
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Palm Oasis Villa East is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This ...
From $262 per night (USD)
VRBO
From $411 per night (USD)
Expedia
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 $411 per night (USD)
Expedia
From $713 per night (USD)
VRBO
Luxury Home with Pool and Dock for Fishing!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Pelican's Nest by AMI Locals Home in Anna Maria, Florida VR20-000006 Experience the ultimate canal front escape at Peli ...
From $713 per night (USD)
VRBO
From $1306 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 $1306 per night (USD)
VRBO
From $386 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 $386 per night (USD)
VRBO
From $378 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 $378 per night (USD)
Expedia
From $212 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 $212 per night (USD)
VRBO
From $820 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 $820 per night (USD)
VRBO
From $343 per night (USD)
VRBO
Spacious 3 bedroom town home on Anna Maria Island, community pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
For your relaxing and family fun, Anna Maria Island vacation, check out this spacious beautiful 3 bedroom, 2.5 bath town ...
From $343 per night (USD)
VRBO
From $1774 per night (USD)
Expedia
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 $1774 per night (USD)
Expedia
From $418 per night (USD)
VRBO
Gulf Place Unit 2 in Holmes Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
**ASK ABOUT LAST MINUTE DEALS! If you like to be close to everything AND have the beach right out your back door, Gulf ...
From $418 per night (USD)
VRBO
From $180 per night (USD)
Expedia
Quiet Nights of Quiet Stars on Anna Maria Island
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Quiet nights of quiet stars, quiet walks by quiet sea, quiet thoughts on quiet location, oh how lovely . . . Great dea ...
From $180 per night (USD)
Expedia
From $726 per night (USD)
VRBO
Everything inside is new and beachy! Two blocks to Bean Point Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our vacation home is two blocks to either the Gulf of Mexico or Tampa Bay…Bean Point Beach! We have remodeled the entire ...
From $726 per night (USD)
VRBO
From $517 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:
4
Island Time by Anna Maria Life Vacation Rentals 426 Spring Ave., Anna Maria, FL 34216 What You'll Love About This Home ...
From $517 per night (USD)
Expedia
$\South Cay\ - Close to Gulf beach, Large Pool$
From $645 per night (USD)
VRBO
\"South Cay\" - Close to Gulf beach, Large Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
<p>LARGE Heated Pool, 2 MB Suites. "South Cay" is very close to Gulf Beach (look us up). Only 11 houses to Gulf beach - ...
From $645 per night (USD)
VRBO
From $1032 per night (USD)
Expedia
SEPT,-OCT. 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 $1032 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $1058 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 Home in Anna Maria, Florida Welcome to Hip Nautic, the ultimate luxury beach retreat on Anna ...
From $1058 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Coccoloba by Duncan Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Coccoloba! This beautiful single-family home is located across from the sugar sand beaches in Holmes Beach. Y ...
From $461 per night (USD)
VRBO
From $559 per night (USD)
Expedia
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 $559 per night (USD)
Expedia
From $269 per night (USD)
VRBO
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 $269 per night (USD)
VRBO
From $2680 per night (USD)
Expedia
Luxury Canalfront Retreat with Dock, Pool, Spa and Game Room
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Yacht Sea by Anna Maria Island Accommodations 50 N Shore Dr Anna Maria, FL 34216 VR21-000021 Welcome to Yacht Sea ...
From $2680 per night (USD)
Expedia
From $824 per night (USD)
VRBO
OCT DEAL Waterfront/Dock/Pool/ Hot Tub/Putting/ Beach by AMIHomeRental
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
Last Minute Deal Oct 24 - Nov 1, 2025 now $2,599/wk* plus fees and taxes Recently Added in 2025 - outdoor cabana over d ...
From $824 per night (USD)
VRBO
From $612 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 $612 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 $641 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 $641 per night (USD)
Expedia
From $667 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 $667 per night (USD)
VRBO
From $936 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 $936 per night (USD)
Expedia
From $687 per night (USD)
VRBO
Anna Maria Gem! Pool, Canal Views & 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 Maria ...
From $687 per night (USD)
VRBO
From $954 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, spa and ...
From $954 per night (USD)
Expedia
From $492 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 $492 per night (USD)
VRBO
From $845 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 $845 per night (USD)
Expedia
From $581 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 $581 per night (USD)
VRBO
From $388 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 $388 per night (USD)
Expedia
From $951 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 $951 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 $1139 per night (USD)
VRBO
Banyan Tree Beach House- Luxury home with private pool
Bedrooms:
4
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 $1139 per night (USD)
VRBO
From $1837 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 Home in Anna Maria, FL Located in the North End area of Anna Maria Island Highlights: • P ...
From $1837 per night (USD)
Expedia
From $422 per night (USD)
VRBO
Pool, Hot Tub and Pet-Friendly Near Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Mangoes on Magnolia by Anna Maria Island Accommodations 313 Magnolia Ave, Anna Maria, FL Welcome to Mangoes on Magnol ...
From $422 per night (USD)
VRBO
From $1253 per night (USD)
Expedia
AcquaLuxe – AMI Luxury Canal-Front w/ Pool, Spa & Dock Near Beaches
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to AcquaLuxe! On Anna Maria Island (Anna Maria, FL) Escape To AcquaLuxe, A Luxury AMI Canal-Front Retreat With ...
From $1253 per night (USD)
Expedia
From $505 per night (USD)
VRBO
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 $505 per night (USD)
VRBO
From $745 per night (USD)
Expedia
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 $745 per night (USD)
Expedia
From $1298 per night (USD)
VRBO
Bikini Bottom: One Block to Pine,3 Blocks to Beach, Dog Friendly, Pool, by Anna Maria Life
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bikini Bottom by Anna Maria Life Vacation Rentals 302 Spring Ave, Anna Maria, FL 34216 What You'll Love About This Home ...
From $1298 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Maritime Memories by Duncan Real Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the newly 2025 renovated and updated Maritime Memories! This north-end 3 bedroom plus den multi level home is ...
From $528 per night (USD)
Expedia
From $774 per night (USD)
VRBO
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 $774 per night (USD)
VRBO
From $796 per night (USD)
Expedia
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 $796 per night (USD)
Expedia
From $738 per night (USD)
VRBO
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 $738 per night (USD)
VRBO
From $639 per night (USD)
Expedia
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 $639 per night (USD)
Expedia
From $245 per night (USD)
VRBO
Dog-Friendly 4 Mins to the Beach & Pine Ave - A Place in Paradise Unit B
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Place in Paradise Unit B by Anna Maria Island Accommodations Duplex in Anna Maria, Florida 34216 VR16-000529 Welcome ...
From $245 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Family-Friendly Duplex Near Beaches & Local Shops - A Place In Paradise Unit A
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Place In Paradise Unit A by Anna Maria Island Accommodations Duplex in Anna Maria, FL Welcome to A Place in Paradise ...
From $299 per night (USD)
Expedia
From $499 per night (USD)
VRBO
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 $499 per night (USD)
VRBO
From $2091 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 $2091 per night (USD)
Expedia
From $573 per night (USD)
VRBO
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 $573 per night (USD)
VRBO
From $850 per night (USD)
Expedia
Blue Palm: Luxury home, heated pool, hot tub, close to beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to Blue Palm, your next vibrant home-away-from-home here in Anna Maria. Constructed in 2016 by luxury builders M ...
From $850 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Coquina Cottage B by Duncan Real Estate
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Coquina Cottage B! Coquina Cottage B is exceptionally located at the northern end of Anna Maria Island, just ...
From $344 per night (USD)
VRBO
From $1252 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 $1252 per night (USD)
Expedia
From $1356 per night (USD)
VRBO
Luxury home with Pool and Spa, Rooftop deck, Water views, Golf cart, and Bikes!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sweet Caroline by AMI Locals Home in Anna Maria, FL 34216 VR23-000009 A modern beach house with a rooftop deck with be ...
From $1356 per night (USD)
VRBO
From $910 per night (USD)
Expedia
Pier to Pier Paradise by Beach Boutique Rentals
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
This stunning 4-bedroom home, aptly named Pier to Pier Paradise, offers breathtaking views of the Bay, luxury amenities, ...
From $910 per night (USD)
Expedia
From $855 per night (USD)
VRBO
Deja Blu:1 Block to Beach! Tropical Oasis, Poolside Lounge, Pool & Spa by Anna Maria Life
Bedrooms:
2
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 $855 per night (USD)
VRBO
From $583 per night (USD)
Expedia
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 $583 per night (USD)
Expedia
From $552 per night (USD)
VRBO
Mon Ami: Pine Ave Location! Pool! 3 Blocks to Gulf or Bay by Anna Maria Life Vacation Rentals
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
311 Pine Ave, Anna Maria, FL 34216 What You'll Love About This Home: Location! On Pine Ave! 2 Blocks to Beach! 3 Blocks ...
From $552 per night (USD)
VRBO
From $870 per night (USD)
Expedia
Sea Creatures Cottage: Steps to beach! Putting Green, Rooftop Deck, Pool by Anna Maria Life
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Sea Creatures Cottage by Anna Maria Life Vacation Rentals 112 Mangrove Ave, Anna Maria, FL 34216 What You'll Love About ...
From $870 per night (USD)
Expedia
From $1319 per night (USD)
VRBO
Coastal home near the shopping district and Gulf beaches
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
Cloud Nine on Pine 303 Pine Ave. Anna Maria FL 34216 Welcome to Cloud Nine on Pine, an incredible newly constructed coa ...
From $1319 per night (USD)
VRBO
From $603 per night (USD)
Expedia
Bay 2 Bay: Bay Across Street! Amazing Views of Bay & Canal, Pool & Lounge by Anna Maria Life
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bay 2 Bay by Anna Maria Life Vacation Rentals 803 S. Bay Drive, Anna Maria, FL 34216 What You'll Love About This home: ...
From $603 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Anna Maria Island Direct Beachfront Condo- Awesome View and Amazing Sunsets
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
View dolphins, terns, gulls, sandpipers, and other shorebirds from your 22 foot wide screened lanai. Walk directly out ...
From $426 per night (USD)
VRBO
From $699 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 $699 per night (USD)
Expedia

Search Your Destination Now!

Anna Maria Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 1,000 Rentals