Carefree Cottage - Magnificent Rosemary Beach home w a private

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House For Rent Daily, Weekly, Monthly

143 Wiggle Lane

Rosemary Beach, Florida 32461


Nightly Rates: $785 - 2,138

 4.5   Sleeps 12

Minimum Stay: 3-7 nights

Pool: Yes  Sq Ft: 2713

Private Pool

 Pet Friendly: No

Availability Calendar  |  Rates  |  Description  |  Amenities  |  Map  |  Reviews
 

*** 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 heat may be added for $45/day plus tax)
* 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

Rate Types: N - Nightly, W - Weekly, We - Weekend, Mw - Midweek, M - Monthly
FromToTypeDaily RateMin.
Stay
4/18/1912/31/36N$785-2,1383
4/18/1912/31/36W$811-2,3087
4/18/1912/31/36M$621-2,00830
4/18/1912/31/36Mw$785-2,0183

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Amenities:

  • king
  • shower
  • toilet
  • twin/ single
  • bay/sound
  • marina
  • playground
  • restaurants
  • Dining
  • Satellite / Cable
  • Stereo
  • Television
  • Smart TV
  • Air Conditioning
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Desk
  • Wifi
  • Free Wifi
  • Wifi Speed 500+ Mbps
  • Desk Chair
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Kitchen Island
  • Dishes & Utensils for Kids
  • beachcombing
  • eco tourism
  • outlet shopping
  • paddle boating
  • photography
  • scenic drives
  • sight seeing
  • walking
  • ATM/bank
  • fitness center
  • Beach
  • Near The Ocean
  • Village
  • Balcony
  • Bicycles
  • Deck / Patio
  • Outdoor Grill
  • Fenced Pool
  • Communal Pool
  • Heated Pool
  • Indoor Pool
  • Private Pool
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • golf
  • jet skiing
  • pier fishing
  • roller blading
  • children welcome
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters
  • flexible
  • not necessary
  • Dining Area
  • Housekeeper Optional
  • Adventure
  • Away From It All
  • Family
  • Romantic
  • Tourist Attractions
  • Outdoor lighting
  • Deadbolt lock on entryway
  • Smoke detectors
  • Fire extinguisher
  • Emergency phone number: Medical
  • Emergency phone number: Police
  • Emergency phone number: Fire
  • Enhanced cleaning practices
  • Clean with disinfectant
  • No-contact check-in and check-out
  • High touch surfaces cleaned with disinfectant
  • Towels and bedding washed in water that's at least 60sC/140sF
  • Follow industry association cleaning practices
  • SafeHome (VRMA & VRHP)
  • Full Kitchen
  • Full-Size Refrigerator
  • Standard Coffee Maker
  • Toaster
  • High Speed WIFI Internet
  • Linens & Towels Included
  • Air Conditioning
  • Ironing Board & Iron
  • Sonos Sound System
  • Nearby ATM
  • Nearby Post Office
  • Nearby FedEx
  • Nearby Bank
  • Nearby UPS Store
  • Neaby Publix Grocery
  • Area Fitness Center
  • Nearby Medical Services
  • Nearby Grocery
  • Outlet Shopping
  • Movie Theatres
  • Golf Course
  • Indoor Neighborhood Pool
  • 4 Private Neighborhood Pools
  • Private Neighborhood Pools
  • Town Events
  • Private Pool
  • Shared Pool
  • Beach
  • Private Beach Access
  • Near Beach
  • Close to Town Center
  • Near Pool
  • Close to Shops and Restaurants
  • Cable TV
  • Apple TV
  • Sonos Sound System

Internet Access Available: Yes

Pool: Yes

Outdoor Shower: Yes

BBQ: Yes

Sauna: Yes

Foosball Table: Yes

Fire Pit: Yes

Kayak/Boogie Boards: Yes

Policies:
Check-InCheck-Out
16:0010:00

Pets Not Allowed
Cancellations. Reservations may be modified, canceled, or shortened only if you provide timely written notice to prior to the Cancellation Period Expiration set forth below. If timely modified, canceled, or shortened, the full amount of your reservation deposit will be refunded, less a $200 cancellation fee and the non-refundable booking fee. In the event of modifications, cancellations, or shortened stays made after the Cancellation Period Expiration, you will be responsible for the full amount of the total booking charges. Any claims for refunds for modifications, cancellations, or shortened stays made after the Cancellation Period Expiration must be sought solely through the vacation travel insurance policy offered by , if such plan was purchased. If you chose to decline the vacation travel insurance plan, no refunds will be provided for modifications, cancellations, or shortened stays made after the Cancellation Period Expiration, and you will be responsible for the full amount of the total booking charges.

Cancellation Period Expiration:
60 Days prior to Guest Check-In: All properties with reservations of less than 14 days
90 Days prior to Guest Check-In: All properties with reservations of 14 days or more

Nearby Activities in Rosemary Beach

Rosemary Beach is a master-planned community along the northwest Gulf coast of Florida. Built on the principles of New Urbanism, this environmentally friendly town contains a variety of housing, recreation, and work opportunities within easy walking distance of each other. Rosemary Beach beach houses are charming and ideally situated for maximum enjoyment of this beach town with a resort atmosphere.

Things To Do in Rosemary Beach

This cozy town was named one of the country's most romantic small towns by CNN. The neighborhoods here are connected by boardwalks and footpaths, so you won't see any cars zipping around town. Swimming pools, playgrounds, tennis courts, shopping, and the beach are all right outside your Rosemary Beach beach house's front door. The beach itself is private to the community members of Rosemary Beach. If you rent or reside in a Rosemary Beach beach house, you receive a security co.. read more

Guest Reviews:
Write a Review!

"Gorgeous Rosemary Beach Property
Beautiful property, our family had a wonderful stay! Our first trip to Rosemary Beach and we can’t wait to book this property again. Our favorite amenities of the home were the floor plan, the beautiful private pool, and the wonderful location. A few days at Rosemary Beach was one of our best vacations yet! Thank you!"
Sep 10, 2025 - , Peck, KS



"A Wonderful home away from home!
We really enjoyed Rosemary and the home was the icing on the cake! It was a block away from the cutest town and a few blocks from the beach. The home was a wonderful spot for our family - the private pool was a game changer. The only thing that was disappointing was home didn’t come with beach towels. We flew so it was a bummer for us to bring our own towels. Please fix this! It would go a long way!"
Aug 25, 2025 - , Fort Wayne, IN



"Carefree Cottage Review - July 2025
Overall the house was great. We've been coming to Rosemary Beach since 2013 and the location is fantastic. We loved the pool and the layout of the house was perfect for 2 families. There were some minor cosmetic issues (scuffed doors and walls, rotted gate outside, etc), the shower hardware came off the wall and there were some ants in one of the bathrooms. None of this was a major problem but we've stayed in nicer houses for less money in the past. Overall it was a great vacation and we enjoyed staying at the property."
Aug 05, 2025 - Kevin D., Houston, TX



"Lovely stay
Home is great!

Pros: beautiful home, wonderful pool, 3rd floor fire pit, quick access to town, first floor living / kitchen.

Cons: AC is great downstairs but bedrooms upstairs can get a bit warm at night. Master fan makes a noise all night when running, Internet is really poor on 2nd and 3rd floor of home (although this might be a general Rosemary Beach issue).

Overall we had a great time and I’d highly recommend the home for any family.

"
Jul 13, 2025 - , Colleyville, TX



"Excellent Experience!
The house was perfect for our Rosemary Beach getaway! Check in and check out were seamless. The house was in beautiful shape and the rental management team was wonderful in response to our questions! Would definitely book again!"
Jun 16, 2025 - Marvin S., Waco, TX



"Excellent Second Stay at Carefree Cottage
This is our second year in a row staying at Carefree Cottage with 2 families of 8 people (4 kids/ 4 adults) and we had another great experience. Well located with 2 parking spots large enough for 2 suvs, a nice sized pool and more than enough rooms/bathrooms for everyone, we loved staying here again. House was impeccably clean and felt fresh. Lots of seating options in family room and the kitchen had everything we needed. They have a standalone ice machine and ice from the fridge. Pool was a great place to relax after long day at the beach. "
Jun 10, 2025 - Benjamin L., Houston, TX



"Great for a Girl's Trip
This house was perfect for our trip. Plenty of space and amenities for our group. The house is centrally located and within walking distance of all the shops, restaurants, and beaches. The only suggestion we have is to include items you would need for a day at the beach (specifically a cooler you can take and beach towels). The process to rent beach chairs was easy and the directions provided by the owner/property manager were clear. "
Feb 13, 2025 - Jen W., Naperville, IL



"Close to Barrett Square
This is my family's 9th Thanksgiving in Rosemary. We absolutely love everything about spending our Thanksgivings in Rosemary - from the 30A race to welcoming Santa the next day.

This is our first year staying in the Carefree Cottage and thus far was our least favorite rental. The house itself needs some upkeep and with so many beautiful homes in Rosemary at the same price point this is one we won’t be choosing again.

First, the pool was so dirty and never cleaned. When reaching out we were told it would be cleaned on Wednesday and Saturday however this never happened. We wasted $45 a day in heating a dirty pool. (Also, the pool heater was so loud it sounded like an airplane flying by every 15 minutes 24/7.) There were also no pool/beach towels.

The shower wand in the king room was broken and would not stay upright in the holder - resulting in shooting water in every which direction. The master room also has lousy curtains that wouldn’t stay intact on the curtain rod. Overall the rooms were very small and a tight fit for adult sized guests (having only 2 king beds and 6 twins).

One of the four bikes was broken and when reaching out the management company was quick to come by and fix the bike which was greatly appreciated.

The location was super close to Barrett Square. If you enjoy privacy as in being close to town but also away from everything this would be a great location for you. "
Jan 17, 2025 - , Westfield, IN



"Great Vacation Rental
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!! "
Aug 23, 2024 - Susan G., Newton, MA



"Amazing house!
This house was an amazing stay for a bachelorette trip. Perfect location with everything in walking distance! Highly recommend. "
Mar 19, 2024 - , Akron, OH



"Wonderful Stay!
We stayed here for a girls weekend and it was absolutely wonderful. Great location and great house. Everything was very clean and perfect! "
Sep 27, 2023 - Milan O., Dallas, TX



"Great location in Rosemary
The home was very clean and conveniently located within the Rosemary community. "
Apr 17, 2023 - , Houma, LA



"Amazing Home!
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. "
Oct 03, 2022 - Staci K., Cumming, GA



"Perfect Location!
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! "
Sep 28, 2022 - Brie J., Boca Raton, FL



"Rosemary Beach
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!!"
Aug 16, 2022 - , Gray, TN



"Carefree - beyond pleased!
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."
Jun 04, 2022 - , Brentwood, TN



"Carefree143
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. "
May 02, 2022 - , Little Rock, AR



"Amazing house!
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 . The pool and outdoor areas were perfect! Overall, everyone enjoyed this experience! "
Apr 11, 2022 - , Athens, GA



"Beautiful and well appointed home for two families
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. "
Mar 29, 2022 - , Atlanta, GA



"Wiggle Road Propery
Excellent location close to everything "
Nov 23, 2021 - Jane W., Louisville, KY



"Perfect family getaway!
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!"
Aug 26, 2021 - Taylor P., Nashville, TN



"Wonderful!
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!"
May 21, 2021 - Allison B., Chattanooga, TN



"Great space in Rosemary Beach!
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. "
May 08, 2021 - Cristina P., Austin, TX


Contact Information:
Vacation Rental Beach House in Rosemary Beach, Florida

Ad Number: 1348623  1782-210426

Viewed: 5277 times.

Updated: Dec 03, 2025

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