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

Home Rental in Holmes Beach Florida

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...

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Rates from

$367 / night

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Carefree Cottage is a 3-bedroom, 3-bath home in Holmes Beach, Florida, sleeping up to 6 guests in 1,510 square feet. The setting is listed as waterfront nearby and near a beach, with a stated short 2-minute walk to Gulf beaches. Standout features include a private resort-style pool with an all-natural mosquito spray system, a thatch-covered lanai, and parking for up to 4 vehicles.

Inside, the home is arranged around an open great-room layout with a large HDTV and a kitchen equipped with modern appliances and a dishwasher. Each of the three bedrooms is furnished with a king-size bed, a television, and a private ensuite bathroom, offering consistent comfort and privacy across the sleeping spaces. Stay essentials include air conditioning, ceiling fans, WiFi, washer/dryer, towels and linens, and a well-stocked kitchen setup. Outdoor conveniences include an outdoor shower and a gas grill with propane included, plus beach chairs, a beach wagon, and a beach umbrella.

Good fit for

Family Vacations

Private Pool Resort-style private pool with an all-natural mosquito spray system.

Three King Suites All three bedrooms have king beds, TVs, and private ensuite bathrooms.

Near Gulf Beaches Described as a short 2-minute walk to Gulf beaches.

Thatched Lanai Thatched-covered lanai with outdoor seating and an outdoor shower.

Parking For 4 On-site parking is available for up to 4 vehicles.

Waterfront - NearbyLocation Setting

Near a BeachBeach Access

3 BedroomsBedrooms

3 Full BathroomsBathrooms

Sleeps 6Guest Capacity

1510 sq. ft.Living Space

Pool (Private)Pool

Internet AccessInternet

TelevisionTelevision

YesAir Conditioning

YesWasher / Dryer

Holmes Beach Florida

208 55th St, Holmes Beach Florida 34217

Location & nearby Explore the Area

Carefree Cottage is in Holmes Beach, Florida, in the South Gulf Coast region. The setting is listed as waterfront nearby and near a beach, and the description notes a short 2-minute walk to Gulf beaches. The home is in a residential area with quiet hours from 10 p.m. to 7 a.m., so guests should plan for a neighborhood setting and keep noise to a respectful level.

Holmes Beach Vacation Rentals Holmes Beach Travel Guide Artists' Guild of Anna Maria Island Anna Maria Island Beach Cafe in Holmes Beach FL

Rates from

$367 per night

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Season	Nightly	Weekly	Monthly
Aug - Dec 2026 Aug 01, 2026 - Nov 20, 2026	$367	n/a	n/a
Thanksgiving 2026 Nov 21, 2026 - Nov 27, 2026	$459	n/a	n/a
Aug - Dec 2026 Nov 28, 2026 - Dec 18, 2026	$367	n/a	n/a
Christmas 26 Dec 19, 2026 - Dec 25, 2026	$483	n/a	n/a
New Year 26 Dec 26, 2026 - Jan 01, 2027	$506	n/a	n/a
Jan 2027 Jan 02, 2027 - Jan 29, 2027	$400	n/a	n/a
Feb 2027 Jan 30, 2027 - Feb 26, 2027	$627	n/a	n/a
Spring Break 2027 Feb 27, 2027 - Mar 19, 2027	$684	n/a	n/a
Easter 2027 Mar 20, 2027 - Apr 02, 2027	$725	n/a	n/a
Post Easter 27 Apr 03, 2027 - Apr 16, 2027	$684	n/a	n/a
Spring 2027 Apr 17, 2027 - May 28, 2027	$483	n/a	n/a
Summer 2027 May 29, 2027 - Jul 02, 2027	$552	n/a	n/a
4 July 2027 Jul 03, 2027 - Jul 09, 2027	$575	n/a	n/a
Summer 2027 Jul 10, 2027 - Jul 30, 2027	$552	n/a	n/a
End of Summer 2027 Jul 31, 2027 - Aug 13, 2027	$414	n/a	n/a
Aug / Sept & Nov / Dec 2027 Aug 14, 2027 - Oct 01, 2027	$367	n/a	n/a
October 2027 Oct 02, 2027 - Oct 29, 2027	$391	n/a	n/a
Aug / Sept & Nov / Dec 2027 Oct 30, 2027 - Nov 19, 2027	$367	n/a	n/a
Thanksgiving 2027 Nov 20, 2027 - Nov 26, 2027	$459	n/a	n/a
Aug / Sept & Nov / Dec 2027 Nov 27, 2027 - Dec 17, 2027	$367	n/a	n/a
Christmas 2027 Dec 18, 2027 - Dec 24, 2027	$483	n/a	n/a
New Year 2027 Dec 25, 2027 - Jan 07, 2028	$506	n/a	n/a
Jan 2028 Jan 08, 2028 - Feb 04, 2028	$400	n/a	n/a
Feb 2028 Feb 05, 2028 - Mar 03, 2028	$627	n/a	n/a
Spring Break 2028 Mar 04, 2028 - Apr 14, 2028	$684	n/a	n/a
Easter 2028 Apr 15, 2028 - Apr 21, 2028	$725	n/a	n/a
Spring 2028 Apr 22, 2028 - May 26, 2028	$483	n/a	n/a
Summer 2028 May 27, 2028 - Jun 30, 2028	$552	n/a	n/a
4th July 2028 Jul 01, 2028 - Jul 07, 2028	$575	n/a	n/a
Summer 2028 Jul 08, 2028 - Jul 28, 2028	$552	n/a	n/a
End of Summer 2028 Jul 29, 2028 - Aug 11, 2028	$414	n/a	n/a
Aug / Sept & Nov / Dec 2028 Aug 12, 2028 - Sep 29, 2028	$367	n/a	n/a
October 2028 Sep 30, 2028 - Nov 03, 2028	$391	n/a	n/a
Aug / Sept & Nov / Dec 2028 Nov 04, 2028 - Nov 17, 2028	$367	n/a	n/a
Thanksgiving 2028 Nov 18, 2028 - Nov 24, 2028	$459	n/a	n/a
Aug / Sept & Nov / Dec 2028 Nov 25, 2028 - Dec 22, 2028	$367	n/a	n/a
Christmas 2028 Dec 23, 2028 - Dec 29, 2028	$483	n/a	n/a
New Year 2027 Dec 30, 2028 - Jan 05, 2029	$506	n/a	n/a

Carefree Cottage is a 3-bedroom, 3-bath vacation home in Holmes Beach on Anna Maria Island, accommodating up to 6 guests. The property is listed as waterfront nearby and near a beach, with the Gulf beaches described as a short 2-minute walk away. It also provides practical trip logistics with parking for up to 4 vehicles and a residential-area reminder to observe quiet hours from 10 p.m. to 7 a.m.

The interior centers on an open great-room plan designed for shared time, with a large HDTV and seating for gathering. The kitchen is equipped for day-to-day cooking and longer stays, including a refrigerator, stove, oven, microwave, dishwasher, coffee maker, toaster, blender, freezer, and dishes/utensils.

Sleeping accommodations are organized for privacy: all three bedrooms include a king-size bed, a television, and a private ensuite bathroom. Comfort features include air conditioning, ceiling fans, internet access, and in-home laundry with a washer/dryer. Linens and towels are provided.

Outdoor living is a key part of the setup, with a private pool described as resort-style and paired with an all-natural mosquito spray system. A thatched-covered lanai offers outdoor seating, and the home includes an outdoor shower plus a gas grill (propane included). Beach gear is supplied, including beach chairs, a beach wagon, and a beach umbrella.

A few things that make Carefree Cottage special:

Concierge Collection Property
Holmes Beach on Anna Maria Island - Short 2 min walk to Gulf Beaches
Resort-style swimming pool including an all natural mosquito spray system
Thatched-covered lanai with outdoor seating, outdoor shower
Gas grill (propane included)
Professional Linen Services
Complimentary WiFi
Beach chairs, beach wagon, & beach umbrella
Parking for 4 vehicles

Carefree Cottage is a colorful, tropical retreat in Holmes Beach where relaxation begins the moment you arrive. Set on a quiet street, it offers privacy while keeping you close to beaches and local attractions.

The open layout features a bright great room with a plush sectional and large HDTV, perfect for gathering. A stylish kitchen with navy cabinetry, granite countertops, and modern appliances makes dining and entertaining easy.

Each of the three bedrooms includes a king-size bed, television, and private ensuite bathroom for added comfort. Thoughtful tropical décor and sleek finishes create a relaxing, upscale feel throughout.

Outside, enjoy a resort-style pool, thatched lanai, and inviting spaces for lounging or dining. Just a short walk to the Gulf, this home is your perfect beachside getaway.

SeaBreeze Vacation’s Concierge Collection of homes offers a curated selection of upscale properties designed for travelers seeking comfort, style, and personalized service. Each home including Carefree Cottage is thoughtfully appointed with premium amenities and enhanced by concierge support to help guests plan unforgettable stays. From luxury interiors to seamless guest experiences, the collection delivers a refined and stress-free vacation.

Carefree Cottage is rated in the Elite tier of the SeaBreeze Property Rating System. This system ranks each home based on quality, design, furnishings, and guest-focused amenities. Elite properties provide a high level of luxury with stylish décor, upgraded furnishings, modern appliances, and beautiful outdoor spaces that often include heated pools or spas. Carefree Cottage offers an elevated vacation experience with impressive comfort and thoughtful attention to detail.

Property 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.

SeaBreeze Linen & Amenity Packs - 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

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.

City of Holmes Beach Vacation Rental License: VRC23-000029
Max Occupancy: 6 Guests | Max Vehicles: 4
Quiet Hours: 10 p.m. - 7 a.m. - please respect our island community
Min stay requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.

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

Biking

Fishing

Scuba Diving

Sailing

Wind Surfing

Kayaking

Golfing

Horseback Riding

Boating

Beach

Family Vacations

Spa

Canoeing

Fly Fishing

Deep Sea Fishing

Ocean

Surfing

Featured Amenities

Internet Access

Television

Washer/Dryer

Air Conditioning

Dishwasher

Grill

Pool (Private)

Property Features

Towels/Linens

Hair Dryer

Ceiling Fan(s)

Refrigerator

Coffee Maker

Microwave

Dishes/Utensils

Stove

Toaster

Oven

Freezer

Blender

Parking

Phone

Iron / Ironing Board

Lanai

Suitability

Children Welcome

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.