House in Holmes Beach, FL
6 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Summary:
Welcome to Carefree Cottage, a charming Concierge Collection property in Holmes Beach on Anna Maria Island, just a two-minute stroll from the beautiful Gulf beaches. Relax by the resort-style swimming pool, unwind beneath the thatched-covered lanai, and enjoy the perfect blend of tropical charm, thoughtful amenities, and relaxing island living.
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.
Welcome to Carefree Cottage, a charming Concierge Collection property in Holmes Beach on Anna Maria Island, just a two-minute stroll from the beautiful Gulf beaches. Relax by the resort-style swimming pool, unwind beneath the thatched-covered lanai, and enjoy the perfect blend of tropical charm, thoughtful amenities, and relaxing island living.
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.
Amenities at Carefree Cottage
Non-smoking
No pets allowed
Family friendly
Map of Holmes Beach, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
I would first of all like to say that Sara Rockey is wonderful to work with. The hand written note was a nice touch, she was very attentive to all my needs and was quick to answer any questions I had. She even had a card and small gift for my son to celebrate his 31st birthday, very much appreciated. We have stayed at the Carefree Cottage 4-5 times now. The house is wonderful with all the right amenities. We love the area, it never disappoints. We had the pleasure of enjoying this trip with some of our grandchildren and the house is great for the littles. The the covered patio areas are a wonderful addition. We utilized that space quite a bit. We will definitely be back and highly recommend Seabreeze, they are wonderful and easy to work with. - Carmen, Loveland Ohio
10 / 10Outstanding·Jun 2026
Had an absolutely amazing time in Carefree Cottage due to the beautiful layout, relaxing pool, on hand kitchen amenities, and most comfortable bedding. In addition, Seabreeze made our stay exceptionally easy and carefree with their attentive nature ensuring all our needs were met!
10 / 10Outstanding·Jun 2026
Seabreeze provided excellent customer service and made our stay a fantastic experience. Everything you could need for a great week at the beach. I would highly recommend Seabreeze to everyone as they truly care about the guest experience!!
6 / 10Average·Jul 2023
Beautiful property; love the upgrades from last year but definitely some cleanliness issues that need addressed.
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Top rated by guests
10Outstanding
(44 Ratings)
"I would first of all like to say that Sara Rockey is wonderful to work with. The hand written note was a nice touch, she was very attentive to all my needs and was quick to answer any questions I had...."
Carmen S.Don't miss out! Price and availability may change
