Anna Maria Vacation Rentals

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Sep 24 - Sep 25
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Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Anna Maria

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Outdoor pool, a heated pool

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

10.0 out of 10, Exceptional, (1)
"The house is beautiful!! Plenty of room for a family, and plenty to do!The owner was readily available through messages and the phone if we had any questions. It was an easy process, and an excellent experience!!!I highly recommend this house if you just feel like hanging out, or exploring Anna Maria, it’s a beautiful location!!And don’t forget to go down the slide!! "
The price is ￥81,924
￥218,818 total
includes taxes & fees
Oct 21 - Oct 22
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Charming cottage in quiet area, close to beach & bay.
Sun loungers, beach towels

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (288)
"Clean and quiet and the best location for a weekend getaway! "
Charming cottage in quiet area, close to beach & bay.
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Interior

Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!

9.0 out of 10, Wonderful, (4)
"Well maintained propert and enjoyed our stay."
The price is ￥84,876
￥232,154 total
includes taxes & fees
Sep 28 - Sep 29
Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach

9.8 out of 10, Exceptional, (62)
"Perfect home for a family getaway "
Bean Point Bungalow! Pet Friendly Home with Pool and Walk to Beach
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Exterior

SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (186)
"Bay view was nice "
The price is ￥39,749
￥105,774 total
includes taxes & fees
Sep 26 - Sep 27
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Beachfront - New Listing!
A heated pool

Beachfront - New Listing!

10.0 out of 10, Exceptional, (26)
"We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!"
Beachfront - New Listing!
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Interior

Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park

9.8 out of 10, Exceptional, (90)
"Excellent place for relaxing beach vacation"
Beautiful cottage w/ heated private pool - walk to beach, dining, Bayfront Park
Huge Fall Discounts! New Breathtaking Canal front Home on Best street in AMI!
Sun loungers, beach towels

Huge Fall Discounts! New Breathtaking Canal front Home on Best street in AMI!

10.0 out of 10, Exceptional, (2)
"Great place! Highly recommend."
Huge Fall Discounts! New Breathtaking Canal front Home on Best street in AMI!
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Outdoor dining

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10.0 out of 10, Exceptional, (181)
"The Bungalow was spotless, I had a fantastic stay, thank you !!!"
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
Terrace/patio

Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!

9.4 out of 10, Exceptional, (40)
"Great home with all needed comforts. Beach is right behind it when is low tide, otherwise beach access is only a block away. Home is clean, modern and comfortable with amazing sunrises. "
Bayfront home with amazing water views! Private pool!! Close to Rod & Reel Pier!
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay
Exterior

Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay

9.8 out of 10, Exceptional, (96)
"This property is perfection. It is absolutely spotless and has everything you need for a great vacation. A very short walk to the beach and a great outdoor space with a pool. We lived our stay and will definitely return!"
Angel Fish Cottage, Sweet 2 BR 1 B, Private Pool, Steps to Gulf and Bay
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Beach nearby, sun loungers, beach towels

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (279)
"We had the most wonderful stay. Home and pool was perfect!!!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Outdoor dining

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

8.6 out of 10, Excellent, (42)
"Nice place for long weekend. Close to great restaurants and an easy walk to the beach."
The price is ￥17,123
￥48,691 total
includes taxes & fees
Sep 29 - Sep 30
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
On the beach

Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes

9.8 out of 10, Exceptional, (120)
"Such a beautiful property! We can't wait to go back!"
Pet Friendly Bay-Canal Waterfront! Tiki Bar 5BR, 5BA Huge Pool, 2 Kayaks/Bikes
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
On the beach

Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar

3.0 star property
9.4 out of 10, Exceptional, (13)
"The location and amenities are amazing. Would definitely stay here again."
Newly Renovated Pet Friendly Waterview w/Private Heated Pool/Spa & Cabana Bar
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
A heated pool

South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool

9.8 out of 10, Exceptional, (56)
"Great place "
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
September Golf Cart Special
Fridge, microwave, oven, stovetop

September Golf Cart Special

10.0 out of 10, Exceptional, (1)
"I can’t say enough amazing things about this home. Newly renovated, stylish, very clean, homey and comfortable. Short walk to the beach and a short drive to the shops. Stay, I promise you won’t regret it! "
September Golf Cart Special
September Golf Cart Special
A heated pool

September Golf Cart Special

9.4 out of 10, Exceptional, (34)
"Great property for family with kids. Beach in walking distance, pool for bigger kids when little ones nap, 2 separate indoor sitting spaces. Very clean and real estate company came immediately when we had one problem with the door alarm."
September Golf Cart Special
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!

9.6 out of 10, Exceptional, (71)
"We had a blast and will definitely be back!"
Naut 2 Shabby Cottage Next-Level Pool Area, Darling FL Cottage - Best of Both!
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Beach nearby, sun loungers, beach towels

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

9.8 out of 10, Exceptional, (169)
"We had an amazing week at Don & Sally’s place. This is our 4th trip to AMI and Shell We Dance is by far the best place we have stayed. The decor is so chic & beachy, they thought of everything! Just a 5 min walk to beautiful Bean Point for a beach day or to catch the sunset. The backyard is a tropical oasis, the pool was perfect and the fenced yard is super private and allowed us to bring our pups. We would definitely stay here again."
The price is ￥59,598
￥115,313 total
includes taxes & fees
Sep 25 - Sep 26
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
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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Top Anna Maria Hotel Reviews

Charming cottage in quiet area, close to beach & bay.

Charming cottage in quiet area, close to beach & bay.

10/10 Excellent
"Super clean and felt like home. Cindy provides everything you need. Easy walk to the beach."
Craig M. 4-night trip
Posted 2 days ago
Charming cottage in quiet area, close to beach & bay.

Find out more about Anna Maria

Find out more about Anna Maria

Search for holiday rentals in Anna Maria on Expedia! You can easily find your home rentals, villas, holiday apartments in Anna Maria using one of the methods below:

  • View our selection of featured holiday rentals in Anna Maria
  • Use the map to find apartments and other holiday homes in the Anna Maria neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Anna Maria while they last

Look no further and take a look at our great range of rental properties in Anna Maria!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Anna Maria?

Yes, we give you a choice of vacation rentals close to top points of interest in Anna Maria, or you can go with 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 vacation rentals that Anna Maria has to offer?

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT: Visitors give good reviews to this Anna Maria vacation home rental, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite homes for rent in Anna Maria are SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog and Spacious 7-bedroom home in Anna Maria~ Putt Putt, Ping Pong, 3 blocks to beach!.

How many vacation rentals are there in Anna Maria?

With 784 Expedia vacation rentals, you're sure 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 like Lido Beach and Tampa Bay.

What are vacation rentals like in Anna Maria?

Vacation rentals are private accommodations you can book for a few days or a quick weekend in Anna Maria. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for family trips.