Cottage Rentals in Anna Maria City Pier, FL: Compare 10+ Sites & Save

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112 Best Cottage Rentals in Anna Maria City Pier (Starting from $292)

Cozy Pine Ave Cottage Near Beach
Cozy Pine Ave Cottage Near Beach
Cottage
Anna Maria, FL, 34216, United States
0.5k from Anna Maria City Pier center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.4

Superb

22 reviews

$671
Average price / night
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Charming cottage in quiet area, close to beach & bay.
Charming cottage in quiet area, close to beach & bay.
Cottage
Anna Maria, FL, 34216, United States
0.6k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

301 reviews

$378
Average price / night
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Beautiful Condo on Pine Ave, 2 Blocks to Beach
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Cottage
Anna Maria, FL, 34216, United States
0.6k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
8.8

Fabulous

26 reviews

$765
Average price / night
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Adorable Cottage with Covered Balconies and Private Pool
Adorable Cottage with Covered Balconies and Private Pool
Cottage
Anna Maria, FL, 34216, United States
0.6k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
9.6

Exceptional

45 reviews

$1013
Average price / night
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Serenity Cottage\n
Serenity Cottage\n
Cottage
Anna Maria, FL, 34216, United States
0.7k from Anna Maria City Pier center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Laundry

3 Bedrooms4 Guests
New to Booking
$1581
Average price / night
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Dog friendly home with lanai, internet, and perfect location
Dog friendly home with lanai, internet, and perfect location
Cottage
Anna Maria, FL, 34216, United States
0.7k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$406
Average price / night
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Beautiful Guest House Near the Beach with Private Pool!
Beautiful Guest House Near the Beach with Private Pool!
Cottage
Anna Maria, FL, 34216, United States
0.7k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
8.8

Fabulous

36 reviews

$580
Average price / night
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Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Cottage
Anna Maria, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Free Parking, Heater, Internet

2 Bedrooms6 Guests
9.6

Exceptional

123 reviews

$745
Average price / night
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Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
Cottage
Anna Maria, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
10.0

Exceptional

200 reviews

$523
Average price / night
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Starfish Cottage - One of 3 Cottages, with shared pool
Starfish Cottage - One of 3 Cottages, with shared pool
Cottage
Anna Maria Island, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

49 reviews

$494
Average price / night
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Shell Cottage -With shared pool, 200 feet from the beach
Shell Cottage -With shared pool, 200 feet from the beach
Cottage
Anna Maria Island, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.6

Exceptional

45 reviews

$292
Average price / night
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Seahorse Cottage - With shared pool, 200 feet from the beach
Seahorse Cottage - With shared pool, 200 feet from the beach
Cottage
Anna Maria Island, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.6

Exceptional

55 reviews

$311
Average price / night
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Newly Renovated – Fresh, Modern Cottage Private Pool Just Steps from the Gulf!
Newly Renovated – Fresh, Modern Cottage Private Pool Just Steps from the Gulf!
Cottage
Anna Maria, FL, 34216, United States
0.8k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
10.0

Exceptional

70 reviews

$574
Average price / night
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Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Cottage
Anna Maria, FL, 34216, United States
0.9k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
8.6

Fabulous

10 reviews

$452
Average price / night
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The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Cottage
Anna Maria, FL, 34216, United States
0.9k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

2 Bedrooms6 Guests
9.8

Exceptional

207 reviews

$296
Average price / night
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Blue Heron Cottage - Anna Maria Island
Blue Heron Cottage - Anna Maria Island
Cottage
Anna Maria, FL, 34216, United States
0.9k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
10.0

Exceptional

75 reviews

$349
Average price / night
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Turtle Cottage - Anna Maria Island
Turtle Cottage - Anna Maria Island
Cottage
Anna Maria, FL, 34216, United States
0.9k from Anna Maria City Pier center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

84 reviews

$577
Average price / night
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Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Cottage
Anna Maria, FL, 34216, United States
1.0k from Anna Maria City Pier center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms4 Guests
10.0

Exceptional

300 reviews

$553
Average price / night
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Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Cottage
Anna Maria, FL, 34216, United States
1.0k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

85 reviews

$547
Average price / night
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Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Luxury Beach Cottage for Families on the North Shore of Anna Maria Island
Cottage
Anna Maria, FL, 34216, United States
1.0k from Anna Maria City Pier center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Laundry, Microwave

3 Bedrooms8 Guests
10.0

Exceptional

110 reviews

$864
Average price / night
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Bean Point Beach Cottage -North End of Anna Maria Island lovely sand &  sunsets!
Bean Point Beach Cottage -North End of Anna Maria Island lovely sand & sunsets!
Cottage
Anna Maria, FL, 34216, United States
1.0k from Anna Maria City Pier center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms4 Guests
9.8

Exceptional

7 reviews

$601
Average price / night
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Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Cottage
Anna Maria, FL, 34216, United States
1.1k from Anna Maria City Pier center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1430
Average price / night
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Private Pool - Seaglass Cottage by SeaBreeze Vacation
Private Pool - Seaglass Cottage by SeaBreeze Vacation
Cottage
Anna Maria, FL, 34216, United States
1.1k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

129 reviews

$602
Average price / night
Check Availability
Welcome to Beach Basket – Your Seaside Retreat!\"
Welcome to Beach Basket – Your Seaside Retreat!\"
Cottage
Anna Maria, FL, 34216, United States
1.2k from Anna Maria City Pier center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

49 reviews

$566
Average price / night
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Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Cottage
Anna Maria, FL, 34216, United States
1.2k from Anna Maria City Pier center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
8.8

Fabulous

75 reviews

$641
Average price / night
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Seabreeze Cottage moments from the beach
Seabreeze Cottage moments from the beach
Cottage
Holmes Beach, Anna Maria Island, FL, 34217, United States
1.6k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
10.0

Exceptional

21 reviews

$302
Average price / night
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Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria.  Close to Beaches!!
Ground Floor Two Bedroom Island Styled Home on Beautiful Anna Maria. Close to Beaches!!
Cottage
Holmes Beach, FL, 34217, United States
1.8k from Anna Maria City Pier center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
10.0

Exceptional

13 reviews

$463
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Cottage Rentals in Anna Maria City Pier.

Where to stay in Anna Maria City Pier? Best neighborhoods & areas

Anna Maria City Pier Cottage Rentals on the Map

Frequently Asked Questions

You can explore 112 verified cottage rentals in Anna Maria City Pier. Our listings are sourced from a range of trusted booking providers, giving you access to charming coastal cottages, peaceful countryside escapes, and cozy stays—all in one place.

Cottage rental prices in Anna Maria City Pier vary based on the season, location, and amenities offered. Rates typically start from around $292 per night, with higher prices during peak travel periods or in waterfront locations. Comparing different options can help you find a stay that fits both your preferences and budget.

Many cottages in Anna Maria City Pier feature inviting outdoor areas such as private gardens, patios, or small yards. These spaces are ideal for relaxing, dining outdoors, or enjoying the surrounding scenery. You can use the available filters to quickly find cottages with outdoor features that match your preferences.

Yes, cottages are often a great choice for travelers with pets thanks to their cozy layouts and access to outdoor space. Currently, 22 listings in Anna Maria City Pier welcome pets, making it easier to plan a comfortable stay with your companion.

For busy seasons such as summer holidays or long weekends, it’s a good idea to book your cottage 60 to 90 days in advance. Since cottages are typically smaller and more unique, the most desirable options tend to get reserved quickly during peak periods.

Cottages in Anna Maria City Pier are known for their comfort and charm, often including amenities such as Bedding/Linens, Kitchen, and Laundry. These features help create a relaxing and home-like atmosphere for guests.

Yes, many cottages in Anna Maria City Pier are well-suited for longer stays. They often include essentials like full kitchens, laundry facilities, and comfortable living spaces, making them a practical option for extended vacations or remote work.