Top 50 Anna Maria Island Vacation Rentals

Condos (2,480)
Houses (2,225)
Cottages (294)
Golf rental (3,751)
Beachfront (1,668)
Beach view (1,336)

Explore a selection of Anna Maria Island vacation rentals

Beautiful 2 BR/2 BA condo only steps to the Beach!
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$126 avg/night
2 beds
2 Bathrooms
Guests 4
19 reviews
DRAGONFLY - Southern Charm on Anna Maria's Famous North Shore
Guests10
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$535 avg/night
5 beds
3 Bathrooms
Guests 10
25 reviews
Luxury Suite Near The Beach with Private Pool
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$114 avg/night
2 beds
2 Bathrooms
Guests 4
69 reviews
Stunning,quick walk to beach,amazing heated pool/spa,5 bdrm,12 in...
Guests12
Bedrooms5
Bathrooms5
Wonderful 5 / 5
$421 avg/night
5 beds
5 Bathrooms
Guests 12
18 reviews
Amazing Coastal House on Holmes Beach!! AUG 13TH-19TH DISCOUNT!!
Guests14
Bedrooms5
Bathrooms6
Wonderful 4.9 / 5
$650 avg/night
5 beds
6 Bathrooms
Guests 14
14 reviews
Gorgeous Sunsets From This Beachfront Home! BIG DISCOUNTS FOR...
Guests26
Bedrooms10
Bathrooms9
Wonderful 5 / 5
$1,071 avg/night
10 beds
9 Bathrooms
Guests 26
9 reviews
Come to Anna Maria Island! Enjoy Your own Private Heated Pool!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$114 avg/night
2 beds
1 Bathroom
Guests 4
32 reviews
INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$112 avg/night
1 bed
1 Bathroom
Guests 4
41 reviews
Beautiful, Ocean-Front Home with Golf Cart & Bikes--Halcyon House
Guests8
Bedrooms3
Bathrooms3
Wonderful 5 / 5
$700 avg/night
3 beds
3 Bathrooms
Guests 8
52 reviews
Cozy Cabana West - Private Heated Pool - 4 Minute Walk to the Beach
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$150 avg/night
2 beds
2 Bathrooms
Guests 6
29 reviews
Luxury Beach Front Home, Breathtaking Gulf Views, 5 Bdrm...
Guests12
Bedrooms5
Bathrooms4
Wonderful 4.8 / 5
$1,071 avg/night
5 beds
4 Bathrooms
Guests 12
31 reviews
A variety of activities to please a whole family no matter what...
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.8 / 5
$199 avg/night
3 beds
3 Bathrooms
Guests 6
19 reviews
Holmes Beach Side Vacation Rental Cottage Walk to Beach, Shopping...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$129 avg/night
2 beds
1 Bathroom
Guests 4
14 reviews
Luxury 2 bed, 2 En Suite Baths, Private Htd Pool, 0 Blocks to...
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$264 avg/night
2 beds
2 Bathrooms
Guests 4
62 reviews
Stunning & luxurious,steps from beach,water views,private heated...
Guests12
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$321 avg/night
5 beds
4 Bathrooms
Guests 12
70 reviews
Gorgeous custom built home on Holmes Beach STEPS TO THE BEACH AND...
Guests16
Bedrooms4
Bathrooms6
Wonderful 4.6 / 5
$602 avg/night
4 beds
6 Bathrooms
Guests 16
21 reviews
INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$110 avg/night
1 bed
1 Bathroom
Guests 4
71 reviews
A Slice Of Paradise . 3 minute walk to the Gulf of Mexico On Anna...
Guests2
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$130 avg/night
1 bed
1 Bathroom
Guests 2
13 reviews
Stunning & luxurious,across beach,ocean views, amazing heated...
Guests12
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$386 avg/night
5 beds
3 Bathrooms
Guests 12
28 reviews
INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...
Guests4
Bedroom1
Bathroom1
Wonderful 4.5 / 5
$108 avg/night
1 bed
1 Bathroom
Guests 4
33 reviews
INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$110 avg/night
1 bed
1 Bathroom
Guests 4
43 reviews
$100 per week discount for September and October! Send Inquiry.
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$157 avg/night
3 beds
2 Bathrooms
Guests 6
16 reviews
Luxury 3 Bed, 3 En Suite Baths, Private Htd Pool, 0 Blocks to...
Guests6
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$280 avg/night
3 beds
3 Bathrooms
Guests 6
47 reviews
Flamingo Beach House - 2 Minute Walk To Beach, Restaurants & Bars...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$186 avg/night
3 beds
2 Bathrooms
Guests 8
26 reviews
Beautiful New Home!!!
Guests13
Bedrooms5
Bathrooms5
Wonderful 4.6 / 5
$771 avg/night
5 beds
5 Bathrooms
Guests 13
20 reviews
Seagrape II-charming & steps to the beach
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$106 avg/night
1 bed
1 Bathroom
Guests 4
31 reviews
Beach Side Studio Vacation Rental on Anna Maria Island steps to...
Guests2
Studio
Bathroom1
Wonderful 4.2 / 5
$54 avg/night
Studio
1 Bathroom
Guests 2
13 reviews
Search No Further! Tortuga Inn # 228 Is The Place To Stay On Anna...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.6 / 5
$180 avg/night
2 beds
1 Bathroom
Guests 6
34 reviews
Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to...
Guests10
Bedrooms5
Bathrooms4
Wonderful 5 / 5
$450 avg/night
5 beds
4 Bathrooms
Guests 10
49 reviews
Anna Maria Island Luxury 2 BR 2 BA Private Heated Pool And Bayou...
Guests6
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$225 avg/night
2 beds
2 Bathrooms
Guests 6
23 reviews
Bay Vista Fall Days start $199/n! 3 BR 2 B Bayfront w/ Panoramic...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$312 avg/night
3 beds
2 Bathrooms
Guests 8
23 reviews
Brand New Renovation Sea Breeze Cottage With Private Dock, Access...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$174 avg/night
2 beds
2 Bathrooms
Guests 6
30 reviews
Anna Maria Rental Steps to Gulf Beach with Private Pool!
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$297 avg/night
3 beds
2 Bathrooms
Guests 8
20 reviews
Best Location on Island - Read Our Guest Reviews!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$99 avg/night
2 beds
1 Bathroom
Guests 4
57 reviews
250 Foot Steps To The Gulf Of Mexico!
Guests4
Bedrooms2
Bathroom1
Wonderful 5 / 5
$139 avg/night
2 beds
1 Bathroom
Guests 4
7 reviews
All The Amenities You Need In One Place Near The Beach, Trolley...
Guests8
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$232 avg/night
2 beds
2 Bathrooms
Guests 8
21 reviews
Your totally PRIVATE Pool awaits / ONLY 1.5 Blocks to Beach
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$164 avg/night
2 beds
2 Bathrooms
Guests 4
30 reviews
Island Condo Just One Block From the Beach
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$129 avg/night
2 beds
2 Bathrooms
Guests 6
17 reviews
Enjoy some fun in the sun on AMI! Lushly landscaped backyard, BIG...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$157 avg/night
3 beds
2 Bathrooms
Guests 6
25 reviews
Less than 200 Steps to the Gulf...Private Heated Pool
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$205 avg/night
3 beds
2 Bathrooms
Guests 6
54 reviews
HURRY! EXTRA LOW RATES for few dates sept/oct/nov Beachfront toes...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$399 avg/night
2 beds
2 Bathrooms
Guests 6
23 reviews
3 minute walk to the beach! Off the main road in a quiet and...
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$143 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
2 Bed 1 Bath Near Beach Pet Friendly And Affordable!!
Guests4
Bedrooms2
Bathroom1
Wonderful 4.3 / 5
$76 avg/night
2 beds
1 Bathroom
Guests 4
18 reviews
Jan. 2018 AVAILABLE! One Block to Beach! 2 bed / 2 bath - West of...
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$192 avg/night
2 beds
2 Bathrooms
Guests 6
42 reviews
Seagrape Cottage - Wonderful Gulf and Sunset Views!
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$140 avg/night
3 beds
2 Bathrooms
Guests 6
37 reviews
No car needed! Grab your suit and hit the beach, 200 foot walk to...
Guests4
Bedrooms2
Bathroom1
Wonderful 4.8 / 5
$135 avg/night
2 beds
1 Bathroom
Guests 4
51 reviews
Bay Front House With Private Dock
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.9 / 5
$200 avg/night
2 beds
2 Bathrooms
Guests 6
44 reviews
Tip of the Island! 3BR, Heated Pool, Canal/Dock, Walk to Beaches...
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.9 / 5
$225 avg/night
3 beds
2 Bathrooms
Guests 8
34 reviews
Spectacular Beachfront House with Pool
Guests8
Bedrooms4
Bathrooms4
Wonderful 4.9 / 5
$1,000 avg/night
4 beds
4 Bathrooms
Guests 8
16 reviews
Anna Maria Island Rentals - Beach Front - "Angels Envy"
Guests4
Bedrooms2
Bathrooms2
Wonderful 5 / 5
$214 avg/night
2 beds
2 Bathrooms
Guests 4
8 reviews

Anna Maria Island, FL, USA Vacation Rentals

Beautiful 2 BR/2 BA condo only steps to the Beach!

DRAGONFLY - Southern Charm on Anna Maria's Famous North Shore

Luxury Suite Near The Beach with Private Pool

Stunning,quick walk to beach,amazing heated pool/spa,5 bdrm,12 in...

Amazing Coastal House on Holmes Beach!! AUG 13TH-19TH DISCOUNT!!

Gorgeous Sunsets From This Beachfront Home! BIG DISCOUNTS FOR...

Come to Anna Maria Island! Enjoy Your own Private Heated Pool!

INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...

Beautiful, Ocean-Front Home with Golf Cart & Bikes--Halcyon House

Cozy Cabana West - Private Heated Pool - 4 Minute Walk to the Beach

Luxury Beach Front Home, Breathtaking Gulf Views, 5 Bdrm...

A variety of activities to please a whole family no matter what...

Holmes Beach Side Vacation Rental Cottage Walk to Beach, Shopping...

Luxury 2 bed, 2 En Suite Baths, Private Htd Pool, 0 Blocks to...

Stunning & luxurious,steps from beach,water views,private heated...

Gorgeous custom built home on Holmes Beach STEPS TO THE BEACH AND...

INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...

A Slice Of Paradise . 3 minute walk to the Gulf of Mexico On Anna...

Stunning & luxurious,across beach,ocean views, amazing heated...

INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...

INN AT THE BEACH! 50 steps to the Beach! Charming 1 bedroom units...

$100 per week discount for September and October! Send Inquiry.

Luxury 3 Bed, 3 En Suite Baths, Private Htd Pool, 0 Blocks to...

Flamingo Beach House - 2 Minute Walk To Beach, Restaurants & Bars...

Beautiful New Home!!!

Seagrape II-charming & steps to the beach

Beach Side Studio Vacation Rental on Anna Maria Island steps to...

Search No Further! Tortuga Inn # 228 Is The Place To Stay On Anna...

Blue Sky: Luxury 5 Bdrm/4 bath with heated pool - 1 block to...

Anna Maria Island Luxury 2 BR 2 BA Private Heated Pool And Bayou...

Bay Vista Fall Days start $199/n! 3 BR 2 B Bayfront w/ Panoramic...

Brand New Renovation Sea Breeze Cottage With Private Dock, Access...

Anna Maria Rental Steps to Gulf Beach with Private Pool!

Best Location on Island - Read Our Guest Reviews!

250 Foot Steps To The Gulf Of Mexico!

All The Amenities You Need In One Place Near The Beach, Trolley...

Your totally PRIVATE Pool awaits / ONLY 1.5 Blocks to Beach

Island Condo Just One Block From the Beach

Enjoy some fun in the sun on AMI! Lushly landscaped backyard, BIG...

Less than 200 Steps to the Gulf...Private Heated Pool

HURRY! EXTRA LOW RATES for few dates sept/oct/nov Beachfront toes...

3 minute walk to the beach! Off the main road in a quiet and...

2 Bed 1 Bath Near Beach Pet Friendly And Affordable!!

Jan. 2018 AVAILABLE! One Block to Beach! 2 bed / 2 bath - West of...

Seagrape Cottage - Wonderful Gulf and Sunset Views!

No car needed! Grab your suit and hit the beach, 200 foot walk to...

Bay Front House With Private Dock

Tip of the Island! 3BR, Heated Pool, Canal/Dock, Walk to Beaches...

Spectacular Beachfront House with Pool

Anna Maria Island Rentals - Beach Front - "Angels Envy"