Carefree Cottage: Anna Maria Island 3 Bedroom Short Term Rental in Holmes Beach FL

Heated Pool
Heated Pool
Living Room
Heated Pool

Carefree Cottage: Anna Maria Island 3 Bedroom Short Term Rental in Holmes Beach FL

Affordable accommodations for families to rent on vacation 3 bedrooms 3 bathrooms in Holmes Beach, FL with pool on Anna Maria Island sleeps 6 : Carefree Cottage

Vacation Cottage in Holmes Beach Florida

208 55th St
How Many Bedrooms? 3 Bedrooms • Sleeps 6
How Many Bathrooms? 3 Full Bathrooms
Virtual Tour: Carefree Cottage - Virtual Tour
How Much Living Space? 1510 sqft.
Location Setting: Waterfront - Nearby
Beach Access: Near a Beach
Air Conditioning: Yes
Pool: Pool (Private)
Internet: Internet Access
Television: Television
Washer/Dryer: Yes
Map of Holmes Beach

Rates & Availability  
(Displayed in USD)

  • Rates From $422 to $825 per night

Rates from $422 per night
Additional fees may apply
Book Direct 101 Rentals Available
Guest Services Team at SeaBreeze Vacation

In Business Since 2011

Daytime Phone Number
Evening Phone Number
Reference this Property as:

Property #165087
Carefree Cottage

Availability details can be found on the SeaBreeze Vacation website.

Book Direct through SeaBreeze Vacation for maximum savings and service!

Availability Details

Season Nightly Weekly Monthly
Sept - Thanks 2023
Aug 05, 2023 - Nov 17, 2023
$422 n/a n/a
Thanksgiving 2023
Nov 18, 2023 - Nov 24, 2023
$468 n/a n/a
Thanks - Dec 23
Nov 25, 2023 - Dec 22, 2023
$422 n/a n/a
Holidays 2023
Dec 23, 2023 - Jan 02, 2024
$630 n/a n/a
Jan 24
Jan 03, 2024 - Jan 27, 2024
$438 n/a n/a
Feb 24
Jan 28, 2024 - Mar 02, 2024
$594 n/a n/a
Spring Break 24
Mar 03, 2024 - Mar 30, 2024
$792 n/a n/a
Easter 24
Mar 31, 2024 - Apr 06, 2024
$825 n/a n/a
Spring Break 24
Apr 07, 2024 - Apr 20, 2024
$792 n/a n/a
Spring 24
Apr 21, 2024 - Jun 01, 2024
$528 n/a n/a
Summer 24
Jun 02, 2024 - Jun 29, 2024
$690 n/a n/a
4 July 24
Jun 30, 2024 - Jul 06, 2024
$720 n/a n/a
Summer 24
Jul 07, 2024 - Aug 02, 2024
$690 n/a n/a
End of Summer 24
Aug 03, 2024 - Sep 03, 2024
$487 n/a n/a
Sept - Thanks 24
Sep 04, 2024 - Nov 22, 2024
$422 n/a n/a
Thankgiving 24
Nov 23, 2024 - Nov 29, 2024
$468 n/a n/a
Thanks - Dec 24
Nov 30, 2024 - Dec 20, 2024
$422 n/a n/a
Holidays 24
Dec 21, 2024 - Jan 04, 2025
$630 n/a n/a

Property Description

Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where all of your cares melt away the moment you walk through the front door. Located on a quiet residential street that offers plenty of peace and privacy yet keeps you close to the beaches and attractions, too, Carefree Cottage has three bedrooms, space for six people, and a resort-style swimming pool in the backyard which includes an all Natural Mosquito Spray System . You can stop looking for your ideal beachy hideaway— it’s right here at Carefree Cottage! The well-designed split floor plan allows for plenty of space and private time, with a wide-open great room in the center for effortless socializing. In the main living area, a plush sectional sofa faces the large HDTV, so you’ll have an inviting spot to watch a game or a great movie with your crew and some yummy snacks. Next to the living space is the open kitchen, where classic navy blue cabinetry and gorgeous granite countertops create a stylish and chic space to prepare some picnic snacks for your beach trip or delicious side dishes for your backyard barbecue. The full suite of premier appliances includes an electric range, a microwave, a dishwasher, and a spacious refrigerator. There’s also a formal dining area with seating for six and a casual bar area with space for three more. Outside, there’s a gas barbecue for grilling out. 

Carefree Cottage features three serene bedroom suites that each have their own bathroom— perfect for families and friend groups that are looking for a smidge more privacy. Each of the three bedrooms has a luxurious king-size bed and an HDTV, and is decorated with colorful tropical decor, while the ensuite bathrooms feature step-in showers and marble vanities. This home was designed to take full advantage of the lovely Gulf coast weather, and the backyard pool area is the ideal spot to soak up the Florida sunshine. With a thatch-covered lanai that allows for endless poolside lounging or alfresco meal options, your group will spend most of their time out here, sipping cocktails and enjoying each other's company. In the evenings, beautiful landscape lighting sets the stage for memorable outdoor gatherings. There’s a full bathroom that’s accessible from the patio and even an outdoor shower— so no one has to track in dripping bathing suites or sandy toes. The Holmes Beach location of Carefree Cottage places your whole crew only one short block from the beautiful Gulf of Mexico that everyone has been daydreaming about, while also keeping you close to local shopping and delicious dining opportunities, too. Let all your cares drift away on the gentle sea breeze at Carefree Cottage.

Cancellation Policy - SeaBreeze Vacation has spent a great deal of time and effort into formulating a cancellation policy for you. SeaBreeze Vacation has the most flexible cancellation policy on the Island. You are allowed to cancel your reservation up to 14 days prior to check-in to receive a refund. Additional terms and conditions apply. 

The property participates in our Professional Linen Program.  SeaBreeze Vacation strives to bring only the best quality experience to our guests. To do so, we provide a professional linen service at this property to better enhance your enjoyment while staying here.  This luxury amenity provides you high-quality linens that are in place and ready for your use upon your arrival. Our high-quality linens are laundered in a commercial setting that uses only hypoallergenic, perfume & dye-free soaps assuring all of our guests a comfortable stay.

With all SeaBreeze Vacation properties, we think of the little things to make your vacation special, with a starter pack of 2 rolls of toilet paper per bathroom, 2 rolls of kitchen paper towels, dish soap, dishwasher pods, and laundry detergent pods. We also offer a range of supplemental services including pre-stock grocery shopping and babysitting. Need a pack and play or high chair, etc.? These are available for a small additional fee and will be waiting in the home on your arrival.

This property comfortably accommodates a group of 6.

You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night.  Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.


Activities and Special Interests

This property provides access to the following activities and special interests:

» Biking
» Fishing
» Scuba Diving
» Sailing
» Wind Surfing
» Kayaking
» Golfing
» Horseback Riding
» Boating

Featured Amenities

» Pool (Private)
» Internet Access
» Television
» Washer/Dryer
» Air Conditioning
» Dishwasher
» Grill

Property Features

» Towels/Linens
» Hair Dryer
» Ceiling Fan(s)
» Refrigerator
» Coffee Maker
» Microwave
» Dishes/Utensils
» Stove
» Oven
» Freezer
» Blender
» Parking
» Iron / Ironing Board
» Lanai


» Basketball Court


» Playground

Other Property Amenities

Fire Safety Equipment, Property Inspected

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