Unwind at Carefree Cottage - A Spectacular 3 Bedroom Getaway for 6 Guests

Heated Pool
Heated Pool
Living Room
Heated Pool

Unwind at Carefree Cottage - A Spectacular 3 Bedroom Getaway for 6 Guests

Escape to Carefree Cottage - Your Dream Vacation Rental in Holmes Beach, FL. Immerse yourself in comfort and relaxation with this stunning 3 bedroom getaway, complete with a private pool and top-notch amenities. Biking, fishing, scuba diving, and...


Vacation Home in Holmes Beach Florida

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), Pool
Internet: Internet Access
Television: Television
Washer/Dryer: Yes

Rates & Availability
(Displayed in USD)

  • Rates From $393 to $735 per night

Rates from $393 per night
Additional fees may apply
Book Direct 84 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

Available
Already Booked
Season Nightly Weekly Monthly
Summer 25
Jul 05, 2025 - Aug 01, 2025
$600 n/a n/a
End of Summer 25
Aug 02, 2025 - Aug 15, 2025
$550 n/a n/a
Aug - Thanks 25
Aug 16, 2025 - Nov 21, 2025
$393 n/a n/a
Thanksgiving 25
Nov 22, 2025 - Nov 28, 2025
$446 n/a n/a
Thanks - Dec 25
Nov 29, 2025 - Dec 19, 2025
$393 n/a n/a
Christmas 25
Dec 20, 2025 - Dec 26, 2025
$567 n/a n/a
New Year 25
Dec 27, 2025 - Jan 02, 2026
$630 n/a n/a
Jan 2026
Jan 03, 2026 - Jan 30, 2026
$435 n/a n/a
Feb 2026
Jan 31, 2026 - Feb 27, 2026
$572 n/a n/a
Spring Break 2026
Feb 28, 2026 - Mar 27, 2026
$716 n/a n/a
Easter 2026
Mar 28, 2026 - Apr 10, 2026
$735 n/a n/a
Spring 2026
Apr 11, 2026 - May 29, 2026
$580 n/a n/a
Summer 2026
May 30, 2026 - Jun 26, 2026
$600 n/a n/a
4 July 2026
Jun 27, 2026 - Jul 10, 2026
$675 n/a n/a
Summer 2026
Jul 11, 2026 - Jul 31, 2026
$600 n/a n/a
End of Summer 2026
Aug 01, 2026 - Aug 14, 2026
$550 n/a n/a
Aug - Dec 2026
Aug 15, 2026 - Nov 20, 2026
$393 n/a n/a
Thanksgiving 2026
Nov 21, 2026 - Nov 27, 2026
$446 n/a n/a
Aug - Dec 2026
Nov 28, 2026 - Dec 18, 2026
$393 n/a n/a
Christmas 26
Dec 19, 2026 - Dec 25, 2026
$567 n/a n/a
New Year 26
Dec 26, 2026 - Jan 01, 2027
$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, 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 suits 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. Included to get you started are the following: 

Per Guest: 1 Bath Towel, 1 Hand Towel, 1 Washcloth, 1 Pool/Beach Towel
Per Full Bathroom: 2 Rolls of Toilet Paper, Hand Soap, Shower Products Set (including trial size shampoo, conditioner, shower gel, and body lotion), Cosmetic Cloth, Bath Mat
Per Kitchen: 2 Rolls of Paper Towels, Hand Soap, Dish Soap, Sponge, Dishwasher Pods (x4), Laundry Detergent Pods (x4), All-Purpose Disinfectant, Microfiber Cloth, 2 Kitchen Towels

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.

VRC23-000029


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
» Beach

Featured Amenities

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

Property Features

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

Entertainment

» Basketball Court

Outdoor

» Playground

Suitability

» Children Welcome

Other Property Amenities

Fire Safety Equipment, Property Inspected

Experience the ultimate tranquility at Carefree Cottage, a 3-bedroom haven designed for up to 6 guests. Revel in its tropical paradise ambiance, luxurious amenities, and prime location at 208 55th St. Unwind in the elegant decor and coastal charm throughout, with a cozy reading nook and modern entertainment system to relax with. Step outside to the resort-style swimming pool, situated in peaceful surroundings with a thatch-covered lanai and a gas barbecue awaiting your enjoyment. Discover the beauty of this outdoor oasis, where every moment promises serenity and comfort.

Property Highlights

Highlighted by its luxurious amenities and prime location, the Carefree Cottage Getaway at 208 55th St offers a relaxing retreat with three bedrooms, resort-style swimming pool, and a tropical paradise ambiance. The bedroom retreats boast serene settings with luxurious king-size beds, HDTVs, and colorful tropical decor, providing a tranquil escape for guests. Each ensuite bathroom features step-in showers and marble vanities, ensuring comfort and privacy. The tropical paradise ambiance extends outdoors with a backyard pool area perfect for soaking up the Florida sunshine, a thatch-covered lanai for poolside lounging, and a gas barbecue for outdoor grilling. Ideal for families and friend groups seeking relaxation and freedom, this property truly embodies the essence of a carefree getaway.

Interior Luxuries

Boasting a sophisticated blend of modern comforts and coastal charm, the interior of the Carefree Cottage Getaway at 208 55th St exudes luxury and relaxation. Guests can indulge in the following interior luxuries: - Cozy reading nook: Curl up with a good book in a charming nook designed for ultimate relaxation. - Modern entertainment system: Enjoy movie nights or catch up on your favorite shows with a state-of-the-art entertainment system. - Designer furnishings: Immerse yourself in stylish and comfortable designer furniture throughout the cottage. - Elegant decor: Admire the elegant coastal decor that creates a tranquil and inviting atmosphere in every room.

Outdoor Oasis

Located within the peaceful surroundings of its backyard retreat, the Carefree Cottage Getaway offers an outdoor oasis where guests can unwind and bask in the Florida sunshine. This poolside paradise beckons visitors to enjoy a tropical retreat with a resort-style swimming pool equipped with a Natural Mosquito Spray System, ensuring a pleasant experience. The thatch-covered lanai provides the perfect spot for poolside lounging, while the gas barbecue allows for easy outdoor grilling. An outdoor shower and full bathroom accessible from the patio add convenience to the outdoor space. Beautiful landscape lighting sets the ambiance for evening gatherings, making this outdoor area a true haven for relaxation and enjoyment under the Florida skies.