Anna Maria Holiday Rentals

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Holiday Rentals in Anna Maria

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Beach nearby

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

9.6 out of 10, Exceptional, (89)
"The property is just as described! It was incredible. The beach and stores were all walking distance. Definitely would stay there again."
The price is AU$1,560
includes taxes & fees
14 Jan - 15 Jan 2025
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Colorful beach cottage w/ heated private pool & grill area - dog-friendly
A heated pool

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

9.0 out of 10, Wonderful, (89)
"The house is in a great location but it’s very dated and and needs work."
Colorful beach cottage w/ heated private pool & grill area - dog-friendly
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (70)
"The Mangrove Cottage was perfect for my family of 4. Great location to the beach! Backyard was like our own tropical oasis! We loved the pool!! Comfortable beds! Hot water lasted a really long time with no issues of running out (4 baths/showers, dishes and laundry on same evening). I enjoyed the sitting in the screened porch in the mornings drinking my coffee. Washer and dryer worked really well. House cleaning staff could have done a better job, but it wasn't terrible. The dishes could...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Convenient Condo Near the Beach w/Shared Pool, Washer/Dryer, Free WiFi, & More
Outdoor dining

Convenient Condo Near the Beach w/Shared Pool, Washer/Dryer, Free WiFi, & More

9.2 out of 10, Wonderful, (46)
"This place is awesome!! Amazing location and has everything you need (except coffee). The staff is incredibly communicative…anything you need they text right back!! Had a great time! Thank you!"
Convenient Condo Near the Beach w/Shared Pool, Washer/Dryer, Free WiFi, & More
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
A heated pool

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (76)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Canal front with Dock and Pool -Honeywood House
Pool

Canal front with Dock and Pool -Honeywood House

9.2 out of 10, Wonderful, (9)
"We enjoyed our stay. The pool alarms were a bit cumbersome. We didn't need them. The kitchen is not open to the living space. The mattresses need to be changed, especially in the twin/trundle. Otherwise, it was very peaceful, and we enjoyed access to the canal and lounging in the pool!! "
Canal front with Dock and Pool -Honeywood House
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
Outdoor pool, a heated pool

Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!

9.8 out of 10, Exceptional, (68)
"We stopped in Anna Maria Island for three days on our road trip visiting Florida beaches. We loved Anna Maria Island. The Naut 2 Shabby Cottage was the perfect location for exploring the island. We loved the quaint charm of the cottage. "
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Property grounds

Stylish bayside condo with WiFi & pool - close to the beach & restaurants

9.6 out of 10, Exceptional, (88)
"Couple small items need maintenance but otherwise up to date, modern and met our needs"
Stylish bayside condo with WiFi & pool - close to the beach & restaurants
Love Shack on the Water Most desirable location on AMI
Sun-loungers

Love Shack on the Water Most desirable location on AMI

10.0 out of 10, Exceptional, (21)
"Overall location was perfect, accommodations were exactly what we needed for our long weekend. Very inviting. "
Love Shack on the Water Most desirable location on AMI
Waterfront home with beautiful views
Property grounds

Waterfront home with beautiful views

8.8 out of 10, Excellent, (23)
"Great location. Property smelled like cat urine but we understand that this is a pet friendly location. We bought new plugins to manage the smell. A few ants in the kitchen but mostly clean. Shower curtain needs to be replaced in guest bathroom (moldy). The lock was tricky but we replaced the batteries after calling help desk. Overall, we would recommend to others."
Waterfront home with beautiful views
The TipSea Turtle managed by Beach Retreats
A heated pool

The TipSea Turtle managed by Beach Retreats

10.0 out of 10, Exceptional, (15)
"A few of us missed connecting flights thanks to “ Tropical storm/ Hurricane Debby” but once we arrived it made all the travel stress worth it. Beautiful home, kids loved the pool and the beach was amazing. This might be our new annual family destination. "
The TipSea Turtle managed by Beach Retreats
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
Outdoor pool, a heated pool

Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!

10.0 out of 10, Exceptional, (24)
"The property was very just right for a couple, it was clean and well equipped and a 2 minute walk to the beach. It was close to restaurants if needed."
The price is AU$784
includes taxes & fees
10 Jan - 11 Jan 2025
Anna Maria Beach Cottage 110B Updated studio beach cottage, steps to the sand!
AMI Retreat: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals
A heated pool

AMI Retreat: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals

8.8 out of 10, Excellent, (28)
"The house was great, my advice would be if you know guests are coming turn on the fridge, we had a full order of grocery with a warm fridge. Also the bit of mold on the ceiling near the kitchen was gross and the alarm for the pool was annoying being we had no littles. Pool was fantastic and the house was clean"
AMI Retreat: No Storm Damage! Pool Open! by Anna Maria Life Vacation Rentals
Sharks Eye- Original island cottage on historic Pine Ave.
Fridge, microwave, oven, stovetop

Sharks Eye- Original island cottage on historic Pine Ave.

9.8 out of 10, Exceptional, (21)
"I would love to live there! "
Sharks Eye- Original island cottage on historic Pine Ave.
Once Upon A Tide managed by Beach Retreats
Fridge, microwave, oven, stovetop

Once Upon A Tide managed by Beach Retreats

10.0 out of 10, Exceptional, (6)
"We had a two family stay at this home and it was very well stocked with kitchen items and beach accessories. Pool was wonderful and great location on the island!"
Once Upon A Tide managed by Beach Retreats
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Fridge, microwave, oven, stovetop

Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!

9.4 out of 10, Exceptional, (16)
"Survived the hurricane. It was a little rough but they made sure we had somewhere to stay. "
Anna Maria Beach Cottage 110G Updated beach cottage, with pool and beach gear!
Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!
Fridge, microwave, oven, stovetop

Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!

10.0 out of 10, Exceptional, (21)
"A great place for a quick trip with friends!! Well equipped for eating in. Everything you need for the beach"
Aloha Beaches! Newly Renovated 4 Bedroom 3 Bath Home w/ Private Pool!
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
Aerial view

Dog-friendly home with amazing backyard, pool, spa, putting green & game room

9.6 out of 10, Exceptional, (15)
"Very nice walkable neighborhood. Walk to beach and restaurants. "
Dog-friendly home with amazing backyard, pool, spa, putting green & game room
Canal-front home with private dock, covered lanai with heated pool and grill
Beach

Canal-front home with private dock, covered lanai with heated pool and grill

9.2 out of 10, Wonderful, (71)
"I have beer coming to AMI for many years and love staying in the North end. This house is near everything we love about the area. Walking distance to the beach and short car ride or bike ride to AMI pier, Rod and Reel and all the great shops on Pine St. Pool area was great and my grandchildren spent most of their time out there. Also loved being g on the canal. Great getaway"
Canal-front home with private dock, covered lanai with heated pool and grill
JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Exterior

JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (172)
"We loved this beachfront property, it was perfect for our family. The layout was nice, we had space for privacy and togetherness. The views were spectacular from the porch we got to see the sunrise and sunsets. The house is located in an upscale neighborhood within walking distance to Motte Marina. The kitchen had everything you might need to cook, also provided were linens and towels, as well as beach chairs. We hope to return soon."
The price is AU$1,208
includes taxes & fees
19 Dec - 20 Dec
JAN. SPECIALS Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Anna Maria you may be interested in

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Beach nearby

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

9.6 out of 10, Exceptional, (89)
"The property is just as described! It was incredible. The beach and stores were all walking distance. Definitely would stay there again."
The price is AU$1,560
includes taxes & fees
14 Jan - 15 Jan 2025
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow
Colorful beach cottage w/ heated private pool & grill area - dog-friendly
A heated pool

Colorful beach cottage w/ heated private pool & grill area - dog-friendly

9.0 out of 10, Wonderful, (89)
"The house is in a great location but it’s very dated and and needs work."
Colorful beach cottage w/ heated private pool & grill area - dog-friendly
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (70)
"The Mangrove Cottage was perfect for my family of 4. Great location to the beach! Backyard was like our own tropical oasis! We loved the pool!! Comfortable beds! Hot water lasted a really long time with no issues of running out (4 baths/showers, dishes and laundry on same evening). I enjoyed the sitting in the screened porch in the mornings drinking my coffee. Washer and dryer worked really well. House cleaning staff could have done a better job, but it wasn't terrible. The dishes could...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Anna Maria?

Yes, there are holiday rentals close to the most popular sights in Anna Maria, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Anna Maria. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that Anna Maria has to offer?

Canal-front home with private dock, covered lanai with heated pool and grill: This highly rated holiday home rental in Anna Maria is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Anna Maria are WE ARE OPEN, 11/27, Beachfront, PRIVATE BEACH ON THE WATERFRONT, Bring your dog and Canal front with Dock and Pool -Honeywood House.

How many holiday rentals are there in Anna Maria?

With 751 Expedia holiday rentals, you're guaranteed to find just the right place for your Anna Maria stay.

What can I see and do in Anna Maria?

Cultural attractions include Anna Maria Island Museum and Historical Park and Island Players, whereas Anna Maria Beach and Bean Point Beach are a couple of picturesque spots to enjoy the outdoors. While in the area, you can also visit popular places such as Lido Beach and Tampa Bay.

What are holiday rentals like in Anna Maria?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Anna Maria. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip.