Welcome to Anna Maria Island, a gem in Florida that shines with possibilities. With 4,676 cottages to choose from, your perfect vacation is just a click away.

From cozy to lavish, Anna Maria Island offers a wide range of cottages to suit your budget and style. With prices starting from $85 and going up to $5,855, you’re spoilt for choice with amenities such as Kitchen / Kitchenette.

Top Features: Kitchen / Kitchenette, Internet / Wifi, Air conditioner, TV and Laundry

Local Highlights: St. Pete Pier™, Mote Marine Laboratory & Aquarium, Imagine Museum: Contemporary glass art, Bayfront Park and South Jetty Beach

Take the first step towards an unforgettable Anna Maria Island experience. Reserve your cottages today and uncover the hidden gems of Florida.

Top Cottages in Anna Maria Island

Beach nearby, sun loungers, beach towels
5.0
Outstanding(235 Reviews)
Cottage
 in Anna Maria
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
4 guests · 2 bedrooms · 2 baths
Pool · Pets allowed · Kitchen / Kitchenette

Indulge in a peaceful retreat at Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!, our elegant Cottage in Anna Maria Island. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
4.9
Outstanding(245 Reviews)
Cottage
 in Anna Maria
Charming cottage in quiet area, close to beach & bay.
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

Looking for a memorable stay in Anna Maria Island? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
vrbo logo
View deal
2 bedrooms, iron/ironing board, travel crib, WiFi
5.0
Outstanding(167 Reviews)
Cottage
 in Anna Maria
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
5 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Anna Maria Island in our Cottage, Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
4.8
Outstanding(183 Reviews)
Cottage
 in Anna Maria
Note: 30 day minimum rental for January, February, and March, 2025
6 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Soak up the beauty of Anna Maria Island in our Cottage, Note: 30 day minimum rental for January, February, and March, 2025. With a range of amenities such as Air conditioner, Internet / Wifi and Laundry, you'll feel right at home.

$$$$
vrbo logo
View deal
Beach
4.7
Outstanding(149 Reviews)
Cottage
 in Bradenton Beach
Experience the passion of hospitality, cleaning, and good location!
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Anna Maria Island for Cottage, for $316 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Beach nearby
4.7
Outstanding(127 Reviews)
Cottage
 in Bradenton Beach
Experience the passion of hospitality, cleaning, and good location!
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Cottage in Anna Maria Island has everything you need for a rejuvenating stay. Treat yourself to Experience the passion of hospitality, cleaning, and good location!'s exceptional amenities, such as Air conditioner, Internet / Wifi and Balcony / Patio.

$$$$
vrbo logo
View deal
Beach towels
4.8
Outstanding(106 Reviews)
Cottage
 in Bradenton Beach
Charming Stand Alone Beach Rental! Walk 2 BridgeSt
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Discover the beauty of Anna Maria Island with a stay at Charming Stand Alone Beach Rental! Walk 2 BridgeSt, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Outdoor pool, a heated pool
5.0
Outstanding(88 Reviews)
Cottage
 in Anna Maria
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
8 guests · 3 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner
Top rated

Nestled in Anna Maria Island, this Cottage is perfect for your next vacation. Enjoy Luxury Beach Cottage for Families on the North Shore of Anna Maria Island's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Exterior
5.0
Outstanding(95 Reviews)
Cottage
 in Holmes Beach
Coastal Charm Meets Cottage Chic! Sparkling Pool/Spa *4 Doors To The Beach*
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Anna Maria Island, at $793 per night for your next great vacation.

$$$$
vrbo logo
View deal
Beach towels
4.7
Outstanding(106 Reviews)
Cottage
 in Anna Maria
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
6 guests · 2 bedrooms · 2 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi
Most favorited

Looking for a memorable stay in Anna Maria Island? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

$$$$
vrbo logo
View deal
Sun loungers, beach towels
4.7
Outstanding(111 Reviews)
Cottage
 in Holmes Beach
Charming! 1.5 blocks to Beach! Quiet & Convenient.
3 guests · 1 bedroom · 1 bath
Garden · Pool · Kitchen / Kitchenette

The best choice in Anna Maria Island for Cottage, for $157 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
4.6
Outstanding(119 Reviews)
Cottage
 in Holmes Beach
Tropical Paradise On The Beach Permit VRC17-000168
4 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Tropical Paradise On The Beach Permit VRC17-000168, our elegant Cottage in Anna Maria Island. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal

Search by amenity

Vacation rentals with a kitchen in Anna Maria Island

On the beach
5.0
Outstanding(84 Reviews)
Cottage
 in Holmes Beach
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for the perfect place to call home during your trip to Anna Maria Island? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
On the beach
4.9
Outstanding(83 Reviews)
Cottage
 in Holmes Beach
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

This Cottage in Anna Maria Island, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
4.9
Outstanding(83 Reviews)
Cottage
 in Holmes Beach
🌴Summer Special🌴3min walk to beach-Private patio-Close to-Everything&Trolley
6 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Anna Maria Island with a stay at 🌴Summer Special🌴3min walk to beach-Private patio-Close to-Everything&Trolley, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Beach nearby
4.6
Outstanding(102 Reviews)
Cottage
 in Bradenton Beach
Experience the passion of hospitality, cleaning, and good location!
4 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Anna Maria Island for Cottage, for $298 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Fridge, microwave, oven, stovetop
4.6
Outstanding(101 Reviews)
Cottage
 in Holmes Beach
Tropical Paradise Cottage on the Beach VRC17-000167
4 guests · 2 bedrooms · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Anna Maria Island in our Cottage, Tropical Paradise Cottage on the Beach VRC17-000167. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
4.9
Outstanding(63 Reviews)
Cottage
 in Holmes Beach
*SPECIAL* 3 min to the beach! Cozy cottage close to everything! Private patio!
4 guests · 1 bedroom · 1 bath
Pets allowed · Kitchen / Kitchenette · Air conditioner

Experience vacation in Anna Maria Island with our Cottage, *SPECIAL* 3 min to the beach! Cozy cottage close to everything! Private patio!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
5.0
Outstanding(63 Reviews)
Cottage
 in Anna Maria
Blue Heron Cottage - Anna Maria Island
4 guests · 1 bedroom · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This attractive Cottage in Anna Maria Island, $297 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
vrbo logo
View deal
Property view
4.9
Outstanding(68 Reviews)
Cottage
 in Anna Maria
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Anna Maria Island at Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida for $380 for your next trip.

$$$$
vrbo logo
View deal
Sun loungers
4.9
Outstanding(65 Reviews)
Cottage
 in Holmes Beach
Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block to beach.
6 guests · 3 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience vacation in Anna Maria Island with our Cottage, Coastal Cottage On Holmes Beach With Private Heated Pool! 1 Block to beach.. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
vrbo logo
View deal
On the beach
4.8
Outstanding(73 Reviews)
Cottage
 in Bradenton Beach
\"Dream boat\" Beach Front Island Rental With Amazing Views
5 guests · 1 bedroom · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

When traveling to Anna Maria Island, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $482 per night.

$$$$
vrbo logo
View deal
On the beach, sun loungers, beach umbrellas, beach towels
4.9
Outstanding(62 Reviews)
Cottage
 in Holmes Beach
Quiet Nights of Quiet Stars on Anna Maria Island
4 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Anna Maria Island with a stay at Quiet Nights of Quiet Stars on Anna Maria Island, a top rated Cottage with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
vrbo logo
View deal
Beach nearby, sun loungers, beach towels
4.9
Outstanding(67 Reviews)
Cottage
 in Anna Maria
Turtle Cottage - Anna Maria Island
4 guests · 1 bedroom · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Looking for a memorable stay in Anna Maria Island? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
vrbo logo
View deal

Travel inspiration

Keep exploring