Holiday Rentals in Anna Maria
List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 km
533 rentals in Anna Maria.
Sort by:
Tripadvisor Sort
Close to beach, gorgeous 5 bd luxury home! Private Pool, Spa, and Putting Green!
Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Dragonfly - Southern charm on the North end of Anna Maria Island
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Sea Garden Cottage with Direct Beach Access,AC & WiFi - North End Anna Maria Fl
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Steps to Bean Point Beach, Pineapple Breeze is a quaint home with private pool
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
North Island Beach Escape
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Anna Maria, Prive Heated Pool, Lanai
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Serendipity - Beach Front Home on Bean Point , Anna Maria
Holiday Rental House
4 bedrooms
8 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Spoonbill Hideaway-*WINTER SPECIAL*/Huge Pool/Spa/Across from Gulf Beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Bungalow On The Bayou (Best Location on the Island)
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Save time - get the best Anna Maria rentals sent straight to your email!
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Spoil yourselves on the GULF OF MEXICO SUNSET BEACH!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
$200 towards a private fishing charter with Captain Josh with 2020 reservation
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
North End of AMI, Heated/Chilled Pool, Ocean Views, Tropical Oasis with elevator
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
INCLUDED FREE Bikes+Tandem Kayak+Beach Cart! Heated Pool*103 degree Hot tub*Dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Anna Maria Island Rentals - Beach Front - 'Angels Envy'
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Seaside Sanctuary #1 - World's Greatest Sunsets!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Spectacular Beachfront House with Pool
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Seaside Maison, Family Friendly, 3 Blocks to Gulf, 2 Blocks to Rest. & Pine St.
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Tucked Away in Anna Maria
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
NEW!! Amie’s House Modern Coastal Getaway
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Beach, Private Fishing dock, Heated Pool, Tropical Paradise
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Vacation Home with pool/canal front/3 blocks to Gulf beach on Anna Maria Island
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Castaway Cottage + Beach + Heated Private Pool&Spa = R & R! Close to Bean Point!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Gulf front, charming home right on the beach - stunning views & dogs welcome!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Waterfront Luxury North End w/ Dock, Heated Pool, Spa and No Steps!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Island Living, refreshing outdoor shower and pool , pet friendly if approved
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Waterfront Stunning New Luxury Home w/Pool, Spa, Dock, Elevator, Close to Pine
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Jan, Feb, 1 month minimum, Contact for special rates $4K mo, $7500. 2 mo + tax
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check-in
Check-out
Luxury Upscale Beach Home Steps from Gulf of Mexico, Heated Pool, Spa & Golfcart
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Dog-friendly house w/ private, heated pool & entertainment - walk to the beach!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Charming cottage located close to beach - private heated pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Charming Beach Home-with a large, Private Pool -3 Houses to the Beach!!!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Grab your swimsuit!! Private heated pool is now open!!!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Blue Heron Cottage - Anna Maria Island
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Charming cottage with heated pool, tropical landscaping in prime location!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Cute, Beachy, Canal-Front w/Dock on Historic Pine Ave! Steps to Beach and Pier!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Seahorse Cottage - 1820659
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Come relax at the amazing and beautiful Cast Away Cove - 2min walk from beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Family freindly adorable cottage steps to the beach, free trolly on island
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Bayside condo w/ a shared pool - close to the beach & restaurants
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check-in
Check-out
Anna Maria-Villa Tarpon- Ground Level Private Canal/Dock, Saltwater Heated pool
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Adorable Vintage Anna Maria Cottage. Heated Pool! North End! 2 Blocks to Beach!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Stunning Canal front Luxury home! Beautiful tropical backyard Pool and Spa!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Dog-friendly beach bungalow with private, heated pool, balcony, and lanai
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
Adorable Beach cottage just steps Bean Point beach! Great Pool, amazing Location
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Perfect Location!! 3 BED, 2BA on North Side between Beach and Anna Maria Pier
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
123456…
Frequently Asked Questions about Anna Maria
- Yes, here are some popular holiday rentals in Anna Maria that have a pool:\n
- \n
- Gorgeous views,spectacular home! \n
- Enjoy our Beach, Pool and Dock! 100 5-Star Reviews! \n
- 'Island Oasis' A single family North end canal home with pool \n
- Yes, here are some popular holiday rentals in Anna Maria that have internet access:\n
- \n
- Jacaranda Artist Retreat \n
- Gorgeous views,spectacular home! \n
- Enjoy our Beach, Pool and Dock! 100 5-Star Reviews! \n
- The best pet friendly rentals in Anna Maria are:\n
- \n
- Jacaranda Artist Retreat \n
- Gorgeous views,spectacular home! \n
- Sand Castle well appointed home steps from beaches \n
- Some of the most popular kid friendly rentals in Anna Maria are:\n
- \n
- Gorgeous views,spectacular home! \n
- Enjoy our Beach, Pool and Dock! 100 5-Star Reviews! \n
- Blue Heron Waterfront House Anna Maria island \n