We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cheap Anna Maria Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Price per night
£0
£1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighbourhood
268 rentals in Anna Maria.
Sort by:
Tripadvisor Sort
Naut 2 Shabby Bungalow In the Heart of Anna Maria Village
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW Luxury Canalfront Home w/Water View, Pool/Spa, Bikes, Kayaks! 25% OFF Month!
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Beautiful, Gulf-Front Home on Bean Point--Halcyon House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dragonfly - Southern charm on the North end of Anna Maria Island
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Luxury Spacious Waterfront Pool, Spa, Bar, Dock, Near Beaches, Fall $380/n
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Anna Maria rentals sent straight to your email!
North Island Beach Escape
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Anna Maria, Prive Heated Pool, Lanai
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
$200 towards a private fishing charter with Captain Josh with 2020 reservation
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Bungalow On The Bayou (Best Location on the Island)
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Anna Maria Island Rentals - Beach Front - 'Angels Envy'
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Gulf front, charming home right on the beach - stunning views & dogs welcome!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming Cottage! Quiet North- End Oasis, Steps To Bay And Gulf. Heated Pool.
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Tucked Away in Anna Maria
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming house with private heated pool, patio, and grill - steps from beach
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming cottage with heated pool, tropical landscaping in prime location!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Charming cottage located close to beach - private heated pool
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beach, Private Fishing dock, Heated Pool, Tropical Paradise
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Jan, Feb, 1 month minimum, Contact for special rates $4K mo, $7500. 2 mo + tax
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Grab your swimsuit!! Private heated pool is now open!!!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Luxury Butterfly Garden, Steps to Pine Ave, Pool/Spa, Bikes, 4 Houses to Beach
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cancel upto 48hrs Before Check-In, Huge Outdoor Kitchen,Roof Top Deck with Amazi
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Family freindly adorable cottage steps to the beach, free trolly on island
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful home, private pool with water VIEWS! Enjoy Anna Maria Island in Luxury
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Canal (60 Ft) Front Anna Maria Rental House Great for Boaters
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Gorgeous views,spectacular home!
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Shirley's Way Beach House - Panoramic Gulf-Front Home on Anna Maria Island
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Water front luxury home with 7 bedrooms, Pool and Spa, views of Rod 'n Reel Pier
7 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious 5 bedroom, canal front luxury home with private Pool and Spa!
5 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Beautiful, well-maintained home w/ heated private pool - walk to beach, dining
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Hear The Surf/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd/4Ba
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Vibrant Beach House – Heated Private Pool and Steps to the Beach
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
PreviousNext
123456