Carefree Cottage - Magnificent Rosemary Beach home w/ a private pool
House in Rosemary Beach, FL
12 guests · 5 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsPool, Kitchen or Kitchenette, Air conditioner and more
About this house rental
***VRBO Top Rated Home for 2025***
All your 30A vacay dreams come true at Carefree Cottage— a magnificent Rosemary Beach home with a soaring roofline resembling a modern fairytale castle. Carefree Cottage has a private pool, a gorgeous open layout, and dramatic swirls of spiral staircases leading up to the stunning rooftop terrace.
On the first floor, the wide-open great room features a huge wall of windows overlooking the pool. The living area is generous and comfy— with plush armchairs, an inviting sofa, and a built-in relaxation space next to the fireplace that’s the perfect place to catch an afternoon siesta. Crisp white beams frame the driftwood-inspired accents on the ceiling.
In the kitchen, an ample island has bar seating for four, a deep apron sink, dishwasher, ice maker and a microwave. There’s also a spacious stainless steel refrigerator, gas stove with a pot filler, and a double wall oven. There is easy access to the alfresco living area, outdoor kitchen, and barbecue area. Chances are your group will spend most of their time out here, lounging by the sun-drenched pool or having lunch at the outdoor dining table.
Three private, spacious bedrooms on the second floor provide plenty of peaceful sleeping space. On the second floor, the first bedroom has a king-size bed and a full ensuite bathroom. The second bedroom has two twin-size beds. The third bedroom is the dazzling primary suite — complete with a luxurious king-size bed, glass desk, and balcony access. The spa-like ensuite primary bathroom has a double marble vanity and rainfall showerhead. There is also a cozy bunk area with twin-over-twin size beds in the hallway.
Climb the spiral staircase to the third floor and the fourth and final bedroom lair. This bedroom has a fun, loft-like feel with four twin-sized beds and beanbag chairs. There’s also a full bathroom with a double vanity. Outside through the French door is a stunning rooftop patio with a fire pit, pergola, and lounge chairs.
At Carefree Cottage, you’ll be tucked into a quaint Rosemary Beach neighborhood while also being within easy walking distance of bustling Barrett Square and some delicious cafes and eclectic boutiques. The Rosemary Beach walkover is a short walk or bike ride away. Carefree Cottage is like having your very own five-star luxury resort with all the conveniences, comforts, and privacy of home.
HOME HIGHLIGHTS
* Complete Clean Bedding Program
* 4 Free Beach Cruiser Bikes
* Very family-friendly atmosphere
* A private courtyard with a private pool, outdoor kitchen, and living area
* Private Pool (Pool Heating Available For A Daily Fee)
* A short walk to dining, shopping, four community pools, and the beach
FIRST FLOOR
* Large COURTYARD with private, sun-dappled pool, outdoor living area, and kitchen
* LIVING AREA with a sofa, multiple armchairs and ottomans, side tables, a coffee table, a fireplace, a built-in daybed, and HDTV
* Farmhouse-style DINING TABLE
* Open KITCHEN with stainless steel refrigerator, gas range, built-in double ovens, microwave, dishwasher, ice maker, marble countertops, apron sink, and island bar with seating for four
SECOND FLOOR
* First BEDROOM with king-size bed and attached bathroom
* Second BEDROOM with two twin-size beds
* Full BATHROOM
* PRIMARY SUITE with king-size bed, desk space, flatscreen television, balcony access, and ensuite bathroom
* Fourth sleeping area with built-in twin-over-twin size bunk beds
* BALCONY with rocking chairs overlooking the pool area below
* LAUNDRY ROOM
THIRD FLOOR
* Spiral staircase
* Fifth BEDROOM LAIR with four twin-size beds
* Full BATHROOM
* Rooftop TERRACE with seating area and fire pit
All your 30A vacay dreams come true at Carefree Cottage— a magnificent Rosemary Beach home with a soaring roofline resembling a modern fairytale castle. Carefree Cottage has a private pool, a gorgeous open layout, and dramatic swirls of spiral staircases leading up to the stunning rooftop terrace.
On the first floor, the wide-open great room features a huge wall of windows overlooking the pool. The living area is generous and comfy— with plush armchairs, an inviting sofa, and a built-in relaxation space next to the fireplace that’s the perfect place to catch an afternoon siesta. Crisp white beams frame the driftwood-inspired accents on the ceiling.
In the kitchen, an ample island has bar seating for four, a deep apron sink, dishwasher, ice maker and a microwave. There’s also a spacious stainless steel refrigerator, gas stove with a pot filler, and a double wall oven. There is easy access to the alfresco living area, outdoor kitchen, and barbecue area. Chances are your group will spend most of their time out here, lounging by the sun-drenched pool or having lunch at the outdoor dining table.
Three private, spacious bedrooms on the second floor provide plenty of peaceful sleeping space. On the second floor, the first bedroom has a king-size bed and a full ensuite bathroom. The second bedroom has two twin-size beds. The third bedroom is the dazzling primary suite — complete with a luxurious king-size bed, glass desk, and balcony access. The spa-like ensuite primary bathroom has a double marble vanity and rainfall showerhead. There is also a cozy bunk area with twin-over-twin size beds in the hallway.
Climb the spiral staircase to the third floor and the fourth and final bedroom lair. This bedroom has a fun, loft-like feel with four twin-sized beds and beanbag chairs. There’s also a full bathroom with a double vanity. Outside through the French door is a stunning rooftop patio with a fire pit, pergola, and lounge chairs.
At Carefree Cottage, you’ll be tucked into a quaint Rosemary Beach neighborhood while also being within easy walking distance of bustling Barrett Square and some delicious cafes and eclectic boutiques. The Rosemary Beach walkover is a short walk or bike ride away. Carefree Cottage is like having your very own five-star luxury resort with all the conveniences, comforts, and privacy of home.
HOME HIGHLIGHTS
* Complete Clean Bedding Program
* 4 Free Beach Cruiser Bikes
* Very family-friendly atmosphere
* A private courtyard with a private pool, outdoor kitchen, and living area
* Private Pool (Pool Heating Available For A Daily Fee)
* A short walk to dining, shopping, four community pools, and the beach
FIRST FLOOR
* Large COURTYARD with private, sun-dappled pool, outdoor living area, and kitchen
* LIVING AREA with a sofa, multiple armchairs and ottomans, side tables, a coffee table, a fireplace, a built-in daybed, and HDTV
* Farmhouse-style DINING TABLE
* Open KITCHEN with stainless steel refrigerator, gas range, built-in double ovens, microwave, dishwasher, ice maker, marble countertops, apron sink, and island bar with seating for four
SECOND FLOOR
* First BEDROOM with king-size bed and attached bathroom
* Second BEDROOM with two twin-size beds
* Full BATHROOM
* PRIMARY SUITE with king-size bed, desk space, flatscreen television, balcony access, and ensuite bathroom
* Fourth sleeping area with built-in twin-over-twin size bunk beds
* BALCONY with rocking chairs overlooking the pool area below
* LAUNDRY ROOM
THIRD FLOOR
* Spiral staircase
* Fifth BEDROOM LAIR with four twin-size beds
* Full BATHROOM
* Rooftop TERRACE with seating area and fire pit
Amenities
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Rosemary Beach, FL
$$$$
Reviews
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
House is in a fabulous location. Around the corner from Barrett Square and all of the shops/ restaurants. Quick walk to the most spectacular beach as well. Super clean and well stocked (only thing we couldn't find was a can opener :) Property managers were very responsive when we had an issue with the WIFI. Back yard, while not super private, is awesome. Large pool, by Rosemary Beach standards, and the yard gets a nice combination of sun/ shade. Would definitely rent this home again!!
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This house was an amazing stay for a bachelorette trip. Perfect location with everything in walking distance! Highly recommend.
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We stayed here for a girls weekend and it was absolutely wonderful. Great location and great house. Everything was very clean and perfect!
8.0
I’d give it 5 star but the house is somewhat worn and we had no trash pick up during the mid week. Staff addressed all our concerns promptly,
10.0
This house was incredible, and our stay was lovely. No complaints at all! Thanks so much for hosting us!
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The home was very clean and conveniently located within the Rosemary community.
8.0
My husband and I gave 5 days at this home to our adult children for a Christmas present. We absolutely loved it!
The home is beautiful, large and in a great location! All of the bedrooms have there own bathrooms which is so nice but there are two King beds and the rest of the beds are twins which didn’t work well with the other couples in our group. Also, the upholstered furniture needs a rehab. The sofa and chairs are a little tired. With all of this said, We loved our time together in Rosemary and would rent this home again.
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Beautiful house. Clean and well appointed. Beds comfortable. Great location. The house could use a little TLC in places (some touchup paint, broken stone on steps, light in pool not working, power wash exterior, etc - things that a $9000/week home shouldn't have), but overall a great house that I would happily return to. Property Management Company was EXCELLENT! Extremely responsive and attentive. I would give them 10 stars if I could. They did everything that they could to address and resolve any issues. And their work crew were such nice people.
10.0
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Overall, we enjoyed our stay! The location in proximity to the Square was fantastic, and the management company was wonderful. I will agree with some of the other reviews regarding the stairs— there is no first floor bedroom (all bedrooms are on the 2nd and 3rd floors), so be sure to take this into consideration before booking if you’re concerned about climbing steps! We found the house to be well cleaned on arrival— some other reviews mentioned stains on chairs, etc, and I agree that the white slipcovered dining chairs did have stains here & there, but it’s to be expected with white slip covered furniture, and I’m sure these spots could be removed with professional cleaning. We also had some issues with the showers (figuring out how to get the water hot), but eventually we got it! The washer machine was extremely mildewed around the rubber ring (it’s a front load washer), and there was a clear mildew smell inside the washer, so this was the only thing in the house that wasn’t really well-maintained/cleaned— with this being said, though, the management company was quick to respond to our request to have someone stop by and clean it! The only recommendation I have to improve guest accommodations in the future would be for the management company to invest in a larger outdoor dining table! The house sleeps 12, but neither the outdoor or indoor dining table seats that many people— we planned to have an in-home outdoor dinner with a fun tablescape one night, but there weren’t enough seats for all of us at any table (we ended up splitting up to seat some at the kitchen bar and some at the indoor table). Not a real dealbreaker by any means, but definitely something that could improve the outdoor dining space! Overall— definitely recommend this home! Thank you guys for a wonderful stay!
6.0
Rating Details:
The vacation rental was somewhat dirty.
I was somewhat unhappy with the location.
I was somewhat dissatisfied with the condition of the vacation rental.
Overall, I do not recommend this vacation rental.
Reviewer Comments:
Not the best place for small kids or older people. Lots of steps to get to bedrooms. Was not very clean. Outside front porch and pool area was not clean. House was clean in spots but fabric furniture was stained and dirty. Showers were hard to regulate and use safely with small children. One great thing was mattresses in bedroom was great!! Sorry to be so negative, but had to tell the truth about this over priced house!!
6.0
House is great....management communication not so much
Solid house & good location
TV/Showers aren't easy to use. Had to call management to help elderly parents figure out TVS. By the end of the trip we all figured out showers but took 7 days including the teenagers. We had to download apps to computers to get TVs to work.
Entire house was congested from day one. Turns out air filters were upside down & clogged. We had to call to have them changed on Thursday.
Make sure to read your contract. The mgt company sticks to that no matter what. I would not consider pool to be "private". There is one bush btwn the pool from the neighbors. Out of the 7 days that we were there, there were three days that you couldn't sit by the pool bc of the construction next door. Dust, saws, etc. You could not hear anyone talk. Again, all management said was read your contract. They take no responsibility for anything beyond that. Blamed construction schedules out of their hands. I totally understand that but some sort of responsibility and at least notice would have been nice for the price we paid for the house. Don't expect the management company to reach out when you have a need. I called on Wednesday regarding the chlorine and never heard back. Pool isn’t salt water, its chlorine. They came twice on the four days that we could actually sit by the pool to treat it & we were told don’t get in for at least four hours. Pool lights don’t work per pool company.
Check out is at 10am...cleaners arrived at 830am making us feel like we needed to rush around to make sure we got out asap.
Make sure to lock upstairs porch leading to house & gates that lead to staircase going to top floor. We woke up one morning with random beer cans (not from our house) on the porch at the fire pit. I would assume some teens went up there after our family left for dinner.
Doors to outside fireplace on main level are not operational.
Pictures from management company show that you can open them up but in reality you cannot. Something that we were looking forward to. Our family is big on open spaces.
When we arrived there was a note from previous renters in the dishwasher that said "we have been calling for many days to have dishwasher fixed. Told repeatedly that repair people were coming and they never showed". The dishwasher was filled with water, on the second day we did get a “loaner” dishwasher. Asked not to take the blue film off the front.
House itself is very well stocked. Beds are comfortable.
10.0
Carefree - beyond pleased!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Our family had a wonderful time at this lovely property and the service from 30A Luxury was impeccable. The home was clean, well-appointed and the pool was a dream. We had a minor issue during our stay and the management company had it resolved in minutes, not hours like we are used to. You'll love this house and I can't wait to stay here again.
10.0
Carefree143
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
The house was in a good location. It was nice having the bikes to ride to the beach. The house was clean and the kitchen was very well equipped. The only TV that worked easily was the one outside. The one in the living room and second master were impossible to work.
10.0
Amazing house!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Great family Spring break ! The house was in a great location, and was very clean on arrival. Any questions we had were promptly answered by 30A Luxury Vacations. The pool and outdoor areas were perfect! Overall, everyone enjoyed this experience!
10.0
Beautiful and well appointed home for two families
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This home is perfect. Great location next to Rosemary square. Walkable to food, shopping and beach. First floor has open kitchen, dining and family room. Second level has one master, one king room located right next door. There is a room across the floor with two twins. The last room is a bunk room with no door (one of my only complaints). The top floor loft is great for teens and not small kids. House had everything we needed for our weeks stay. The rental company did a superb job supplying any needs and resolving minor issues.
10.0
My daughters very last Spring Break
What an amazing venue & location to preserve the memories of my college daughters VERY LAST Spring Break. It was wonderful spending such valuable time with my precious family members.
10.0
Wiggle Road Propery
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Excellent location close to everything
10.0
Engagement Weekend
This property was absolutely perfect for our very special weekend. My son actually proposed on the rooftop at sunset and we enjoyed the weekend with family by the pool, watching Saturday football games and the proximity of the house to the center of the Rosemary community. I would definitely recommend this house to anyone looking to rent!
10.0
Perfect family getaway!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
House is beautiful and spacious! The downstairs layout and the amazing pool/outdoor living room is ideal for a week of fun! Hoping to go back this Fall to watch football by the pool!
5.0
Rating Details:The property manager was very helpful.The vacation rental was spotless.I was very happy with the location.I was very satisfied with the condition of the vacation rental.Overall, I recommend this vacation rental.Reviewer Comments:All was wonderful! My only complaints would be that this house has no bath tub at all (difficult for small children) and check in time was 5pm. However, both of those things were disclosed prior in the information. Overall, a wonderful stay!
10.0
Wonderful!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
All was wonderful! My only complaints would be that this house has no bath tub at all (difficult for small children) and check in time was 5pm. However, both of those things were disclosed prior in the information. Overall, a wonderful stay!
10.0
Great space in Rosemary Beach!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We enjoyed our stay at the Carefree Cottage. It’s conveniently located, has a great pool (really large), lots of space and a well-stocked kitchen. It was just the 4 of us in our family, so had plenty of space. The mangagment company was very responsive to any requests we had during our stay as well. Beach is about a 7-10 minutes walk or a quick bike ride.
5.0
Rating Details:The property manager was very helpful.The vacation rental was spotless.I was very happy with the location.I was very satisfied with the condition of the vacation rental.Overall, I recommend this vacation rental.Reviewer Comments:We enjoyed our stay at the Carefree Cottage. It’s conveniently located, has a great pool (really large), lots of space and a well-stocked kitchen. It was just the 4 of us in our family, so had plenty of space. The mangagment company was very responsive to any requests we had during our stay as well. Beach is about a 7-10 minutes walk or a quick bike ride.
FAQs
How much does this house cost compared to others in Rosemary Beach?
The average price for a rental in Rosemary Beach is $533 per night. This rental is $498 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Carefree Cottage - Magnificent Rosemary Beach home w/ a private pool. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
Yes, a swimming pool is available for use at Carefree Cottage - Magnificent Rosemary Beach home w/ a private pool. Enjoy the water!
Is Carefree Cottage - Magnificent Rosemary Beach home w/ a private pool pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Carefree Cottage - Magnificent Rosemary Beach home w/ a private pool?
We found 10 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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SANDY SHORES, Private Beach, Private Pool, FULL SIZE ARCADE, beach chairs
House
in Panama City Beach35 guests · 9 bedrooms · 7 baths
Pool · Kitchen or Kitchenette · Air conditioner
This inviting House in Rosemary Beach can fit your needs for many types of vacations, at $892 per night.
$$$$
30A Seacrest Beach Rental Steps to Lagoon Pool + Pet Friendly 'Shore To Please'
House
in Seacrest Beach16 guests · 5 bedrooms · 5 baths
Pool · Pets allowed · Kitchen or Kitchenette
Enjoy the best of Rosemary Beach in our House, 30A Seacrest Beach Rental Steps to Lagoon Pool + Pet Friendly 'Shore To Please'. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Book now for a Holiday Getaway! Private Heated Pool! Short Walk to the Beach!
House
in Rosemary Beach16 guests · 5 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner
Experience vacation in Rosemary Beach with our House, Book now for a Holiday Getaway! Private Heated Pool! Short Walk to the Beach!. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Holiday Stays Available! "Our Blue Beso" 3 King Suites! Walk to the Beach! 4 Adult Bikes!
House
in Seacrest Beach14 guests · 6 bedrooms · 6 baths
Pool · Kitchen or Kitchenette · Air conditioner
Are you ready to indulge in a relaxing getaway? Our House in Rosemary Beach has everything you need for a rejuvenating stay. Treat yourself to Holiday Stays Available! "Our Blue Beso" 3 King Suites! Walk to the Beach! 4 Adult Bikes!'s exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Bella Cottage - Heated Pool, 1 Minute to Beach!
House
in Rosemary Beach12 guests · 4 bedrooms · 5 baths
Garden · Pool · Kitchen or Kitchenette
Looking for the perfect place to call home during your trip to Rosemary Beach? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
Clare’s Cottage - Private Pool, Bikes, 1 Min to Beach
House
in Seacrest14 guests · 5 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner
Experience vacation in Rosemary Beach with our House, Clare’s Cottage - Private Pool, Bikes, 1 Min to Beach. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
5/5.5 Great Gulf Getaway-3,500 Sq Ft
House
in Panama City Beach16 guests · 5 bedrooms · 6 baths
Pool · Kitchen or Kitchenette · Air conditioner
House in Rosemary Beach, for $1,053 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
$$$$
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