Winter Vacation Rentals & Cabin Rentals in Anna Maria Island, FL

Compare 17,154 available beachfront holiday vacation home properties, starts from $14

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in Anna Maria Island, FL: Top Deals

2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
2BR/1BA Vacation Rental - Sienna Park
4.8 (16 reviews)
2BR/1BA Vacation Rental - Sienna Park
Hotel
$70 /night
View deal
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
2 BR Longboat Key Gulf Front Beach Villa
4.5 (10 reviews)
2 BR Longboat Key Gulf Front Beach Villa
House · 6 Guests · 2 Bedrooms
$300 /night*
View deal
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
2BR/2BA condo Sienna Park
4.3 (6 reviews)
2BR/2BA condo Sienna Park
Condo
$80 /night
View deal
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
Gulf and beach view apartment
4.6 (12 reviews)
Gulf and beach view apartment
Apartment
$158 /night
View deal
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
Luxury Beachfront Villa with Gulf Views
5.0 (3 reviews)
Luxury Beachfront Villa with Gulf Views
Villa
$250 /night
View deal
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
Turtle Crawl Inn - Longboat Key
4.1 (99 reviews)
Turtle Crawl Inn - Longboat Key
Hotel
$230 /night
View deal
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
3 Waves From It All by Beachside Management
4.2 (16 reviews)
3 Waves From It All by Beachside Management
Hotel
$155 /night
View deal
Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
Sea Club I
4.3 (52 reviews)
Sea Club I
Hotel
$150 /night
View deal
Beach and sunset view from your balcony
Beach and sunset view from your balcony
Beach and sunset view from your balcony
Beach and sunset view from your balcony
Beach and sunset view from your balcony
Beach and sunset view from your balcony
4.8 (8 reviews)
Beach and sunset view from your balcony
Hotel
$158 /night
View deal
Search all

Similar Inspirational Vacation Rental Destinations

Which Price Range Is Most Typical in Anna Maria Island, FL Area?
Vacation Condo & House Rental Price Information in Anna Maria Island, FL
+
The graph shows the percentages of vacation homes in each price bucket. Anna Maria Island has the largest percentage (29.07%) of homes in $100 - $150 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What are the best activities, communities, and places of interest for snowbirds on Anna Maria Island, FL?
Anna Maria Island, FL: Snowbirds Friendly Places
+
Anna Maria Island is an ideal destination for snowbirds looking to enjoy a warm winter. This barrier island has plenty of attractions that make it perfect for seniors. With its white sand beaches, stunning sunsets, and a plethora of outdoor activities, there’s something for everyone. It's also conveniently located close to medical facilities in case of any emergency.

  • Manatee Public Beach

    This beach features picnic tables, showers, restrooms, and even a concession stand. The beach is wheelchair accessible and has plenty of parking available. It's the perfect spot for snowbirds to soak up the Florida sunshine.

  • The Sandbar Restaurant

    This restaurant is known for its fresh seafood and beautiful waterfront views. It's great for seniors who want to enjoy good food and watch the sunset with their loved ones.

  • Coquina Bay Walk

    Take a leisurely stroll along this boardwalk and enjoy some breathtaking views of the Gulf of Mexico. It's perfect for those who want to take in the beauty of nature without having to worry about a strenuous hike.

How Many Rental Accommodations Are Pets Friendly in Anna Maria Island, FL?
Pets Allowed vs Not Allowed in Anna Maria Island, FL
+
20.30% of vacation homes in Anna Maria Island are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Where Should We Visit in Anna Maria Island, FL Area?
Destinations To Visit During the Winter in Anna Maria Island, FL
+
What are the Airports in Anna Maria Island, FL?
Suggested Airports in Anna Maria Island, FL
+

2 airport(s) close to Anna Maria Island are:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers