Winter's End
Winter's End
Winter's End
Winter's End
Winter’s End by Oversee 30A | 2025 Diamond Winner-Best Rental Mgmt.
Winter’s End is in the heart of historic Seagrove. Modern and wonderfully decorated with distinctive art, the courtyard home was built for luxury living and convenience. With 2,922 sq. ft, it comfortably sleeps 12.
Your entire family will love this luxurious beach sanctuary with a private saltwater pool and spa.
The serene courtyard oasis, complete with comfortable lounge chairs, can be accessed at several points, including a primary bedroom.
Your crew will also take advantage of the complimentary 4-seater golf cart, for zooming to the beaches, shops, and eateries. Or cruise around on one of the 4 complimentary bikes. Never a dull moment.
Check out the stunningly designed interiors and the peaceful screened-in porch on the second floor. With high ceilings, rustic wood beams, and a gas fireplace, the expansive and handsome ground-floor living area is undeniably unique.
The living room, with a large TV, has lots of plush, comfortable seating. The dining area includes seating for 8, along with a side table for 4, which doubles as a game table for rainy days. The impressive chef’s kitchen is equipped with two large sinks, a 5-burner gas range, double wall ovens, and 2 Bosch dishwashers. An exquisite, large quartzite island has additional seating for 5.
A guest bedroom, queen, with a Smart TV, is next to the shared hall bath. A primary bedroom, king, is just as fabulous and includes a massive walk-in shower with multiple shower heads, a double quartzite vanity, and a private water closet.
The second floor includes two guest bedrooms and a shared full bath with a double vanity and tub/shower combo. Relax on the large three-sided screened-in porch, overlooking the courtyard, which includes a comfy swinging seat, a loveseat, a side table, and outdoor fans.
For a truly unique beach escape, take a dip in Winter's End!
Welcome! Our dedicated team at Oversee 30A, a local company, is committed to ensuring your stay is nothing short of exceptional. We strive for perfection and are just a stone's throw away should you require any assistance. Reach out to us anytime, seven days a week, with the added peace of a 24/7 emergency line.
Overview:
- 860 steps (.4 miles) to the beach (San Juan Public Beach Access)
- 4 bedroom, 3 bath
- 2922 sq ft
- Large 8'x20' saltwater pool - (can be heated seasonally for an additional $55.00 per day, contact Oversee for details)
- Gas grill
- Wi-Fi included
- 4 bikes included
- Complimentary 4-seater gas golf cart
- Parking limited to 3 vehicles with no street parking
- Dogs allowed under 50 lb ($210 non-refundable fee)
Overnight:
- King in primary bedroom 1st floor; private shower; TV
- Queen 1st floor; hall shower; TV
- King with twin/twin bunks in 2nd floor guest room; shared hall bath with tub/shower; TV
- Queen with twin/twin bunks in 2nd floor guest room; shared hall bath with tub/shower; TV
Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
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Take the 3D walkthrough.
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Let's watch a video of the home.
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Hassle-free check-in.
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Add your trip dates to get the cancellation details for this stay.
House Rules
Who can stay.
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12 guests maximum
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Pet friendly
What's allowed.
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Check-in after 4:00 PM
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Check-out before 10:00 AM
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No smoking
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No parties or events
Amenities
Indoor
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Wireless internet
Entertainment
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Cable
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Smart TV
Safety Features
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Carbon monoxide detector
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Fire extinguisher
Kitchen
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Standard coffee maker
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Microwave
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Refrigerator
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Toaster
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Dishwasher
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Stove
Bed And Bathroom
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Hair dryer
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Iron & board
Outdoor
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Balcony
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Private pool
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Private heated pool
Complimentary Items
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4 Oversee bikes
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Golf cart
Bed and Baths
1st Floor
bedroom
1 Queen bed
Primary Bedroom
1 King bed
full bathroom
full bathroom
2nd Floor
bedroom
1 King bed 1 Bunk bed
bedroom
1 Queen bed 1 Bunk bed
full bathroom
Location
Upcoming Events
Dueling Pianos
Seagrove
Live Music
The venue hosts a live Dueling Pianos event, which takes place from 7:00 PM to 10:00 PM.
Dueling Pianos
Seagrove
Live Music
The Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Brunch by the Lake
Seagrove
Food & Drink
A Sunday brunch commences every Sunday at 10 a.m.
Football Party
Seagrove
Sports & Games
An announcement was made inviting people to a football party celebrating the Super Bowl.
Football Party
Seagrove
Sports & Games
An announcement was made inviting people to a football party celebrating the Super Bowl.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs live on the Main Stage from 6:30 PM to 9:30 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs on the Main Stage live from 6:30 PM to 9:30 PM.
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is scheduled for every Thursday from 11:30 a.m. to 1:30 p.m. The dates for the event are the 5th, 12th, 19th, and 26th.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Dueling Pianos
Seagrove
Live Music
They can catch Dueling Pianos live from 7 to 10 PM.
Valentine's Dinner Specials
Seagrove
Food & Drink
The event is scheduled to begin at 4:30 PM on February 14th.
Dueling Pianos
Seagrove
Live Music
The event features Dueling Pianos performing live from 7 PM to 10 PM.
Brunch by the Lake
Seagrove
Food & Drink
The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.
Russ Whitten-Main Stage
Seagrove
Live Music
Russ Whitten performs live from 7-10 PM.
Presidents’ Day
Seagrove
Family Fun
It was Presidents' Day.
Russell Brand Show
Seagrove
Arts & Culture
The Russell Brand Show is scheduled for February 16th and 17th at 5:30 PM. Tickets are available for purchase on their website.
Mahjong
Seagrove
Sports & Games
The Mahjong event is held on select Tuesdays from 11:30 a.m. to 4:30 p.m., specifically on the 3rd, 17th, and 24th of the month, and offers participants the opportunity to learn and play the game.
Russell Brand Show
Seagrove
Arts & Culture
Tickets for the Russel Brand Show on February 16th and 17th at 5:30pm are available for purchase on the website.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Ash Wednesday
Seagrove
Arts & Culture
Ash Wednesday is scheduled for 2026.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier-Main Stage performs live from 6:30 to 9:30 PM.
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is held every Thursday from 11:30 am to 1:30 pm on the 5th, 12th, 19th, and 26th.
Dueling Pianos
Seagrove
Live Music
A live Dueling Pianos performance is scheduled from 7:00 PM to 10:00 PM.
Coastside Wine Tasting with John Gibson (Salexis Wines)
Seagrove
Food & Drink
Coastside Wine Tasting with John Gibson (Salexis Wines) is scheduled to take place. Additionally, AJ’s Grayton Beach will host a job fair on February 2nd and February 9th from 12 PM – 5 PM. Applicants interested in positions such as Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers are encouraged to bring their resume and attend ready to interview. Candidates will have the opportunity to meet with hiring managers from the locally owned and operated restaurant group, which has been part of the community for over 42 years, to discuss the various opportunities available across all departments.
Dueling Pianos
Seagrove
Live Music
AJ’s Grayton Beach is holding a job fair on February 2nd and February 9th from 12 PM to 5 PM. The restaurant group is seeking applicants for various departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Interested candidates should attend the event prepared for an interview and bring their resume to meet face-to-face with hiring managers. Additionally, the venue features Dueling Pianos live from 7 PM to 10 PM. The locally owned and operated restaurant group has been serving the community for over 42 years.
Fri, February 6
Dueling Pianos
Seagrove
Live Music
The venue hosts a live Dueling Pianos event, which takes place from 7:00 PM to 10:00 PM.
Sat, February 7
Dueling Pianos
Seagrove
Live Music
The Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Sun, February 8
Brunch by the Lake
Seagrove
Food & Drink
A Sunday brunch commences every Sunday at 10 a.m.
Sun, February 8
Football Party
Seagrove
Sports & Games
An announcement was made inviting people to a football party celebrating the Super Bowl.
Sun, February 8
Football Party
Seagrove
Sports & Games
An announcement was made inviting people to a football party celebrating the Super Bowl.
Tue, February 10
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs live on the Main Stage from 6:30 PM to 9:30 PM.
Wed, February 11
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs on the Main Stage live from 6:30 PM to 9:30 PM.
Thu, February 12
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is scheduled for every Thursday from 11:30 a.m. to 1:30 p.m. The dates for the event are the 5th, 12th, 19th, and 26th.
Thu, February 12
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen performing live from 7 PM to 10 PM.
Fri, February 13
Dueling Pianos
Seagrove
Live Music
They can catch Dueling Pianos live from 7 to 10 PM.
Sat, February 14
Valentine's Dinner Specials
Seagrove
Food & Drink
The event is scheduled to begin at 4:30 PM on February 14th.
Sat, February 14
Dueling Pianos
Seagrove
Live Music
The event features Dueling Pianos performing live from 7 PM to 10 PM.
Sun, February 15
Brunch by the Lake
Seagrove
Food & Drink
The establishment offers a Sunday Brunch every Sunday, beginning at 10 am.
Sun, February 15
Russ Whitten-Main Stage
Seagrove
Live Music
Russ Whitten performs live from 7-10 PM.
Mon, February 16
Presidents’ Day
Seagrove
Family Fun
It was Presidents’ Day.
Mon, February 16
Russell Brand Show
Seagrove
Arts & Culture
The Russell Brand Show is scheduled for February 16th and 17th at 5:30 PM. Tickets are available for purchase on their website.
Tue, February 17
Mahjong
Seagrove
Sports & Games
The Mahjong event is held on select Tuesdays from 11:30 a.m. to 4:30 p.m., specifically on the 3rd, 17th, and 24th of the month, and offers participants the opportunity to learn and play the game.
Tue, February 17
Russell Brand Show
Seagrove
Arts & Culture
Tickets for the Russel Brand Show on February 16th and 17th at 5:30pm are available for purchase on the website.
Tue, February 17
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6:30 PM to 9:30 PM.
Wed, February 18
Ash Wednesday
Seagrove
Arts & Culture
Ash Wednesday is scheduled for 2026.
Wed, February 18
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier-Main Stage performs live from 6:30 to 9:30 PM.
Thu, February 19
Beach Mahjong
Seagrove
Sports & Games
Beach Mahjong is held every Thursday from 11:30 am to 1:30 pm on the 5th, 12th, 19th, and 26th.
Thu, February 19
Dueling Pianos
Seagrove
Live Music
A live Dueling Pianos performance is scheduled from 7:00 PM to 10:00 PM.
Fri, February 20
Coastside Wine Tasting with John Gibson (Salexis Wines)
Seagrove
Food & Drink
Coastside Wine Tasting with John Gibson (Salexis Wines) is scheduled to take place. Additionally, AJ’s Grayton Beach will host a job fair on February 2nd and February 9th from 12 PM – 5 PM. Applicants interested in positions such as Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers are encouraged to bring their resume and attend ready to interview. Candidates will have the opportunity to meet with hiring managers from the locally owned and operated restaurant group, which has been part of the community for over 42 years, to discuss the various opportunities available across all departments.
Fri, February 20
Dueling Pianos
Seagrove
Live Music
AJ’s Grayton Beach is holding a job fair on February 2nd and February 9th from 12 PM to 5 PM. The restaurant group is seeking applicants for various departments, including Bartenders, Servers, Door Staff, Retail Associates, Bussers, Expos, Food Runners, Host Staff, Kitchen Staff, Prep Cooks, and Late Night Bussers. Interested candidates should attend the event prepared for an interview and bring their resume to meet face-to-face with hiring managers. Additionally, the venue features Dueling Pianos live from 7 PM to 10 PM. The locally owned and operated restaurant group has been serving the community for over 42 years.
Reviews - 41
Airbnb
Vrbo
Very clean well equipped home. Pet friendly.
Vrbo
Vrbo
This house was perfect for our family for fall break. The location was close to everything and the golf cart made it super easy to get back and forth to the beach. I highly recommend!
Airbnb
Vrbo
The house is amazing! The rooms, beds and kitchen were just perfect. Great amenities and excellent communication for all the questions we had.
Google
Definitely will be coming back.
Airbnb
Airbnb
Airbnb
Great stay for our family!
Airbnb
Airbnb
Winters End was absolutely stunning, spacious, and everything that we could ask for. The pool was a great size and the patio was very large with tons of seating. We enjoyed the house and the golf cart to get around on as well.
Airbnb
Airbnb
Was a great location! Walkable to beach but a little farther into towns. The golf cart was great for getting around. There were a few things that were broken in the house (golf cart mirror, Keurig), but other than that would recommend. Oversee did a great great job of communicating and helping us.
Airbnb
This house is was a great retreat for our family. The pool was a great relaxation after a long day at the beach. The design of the house was unique and had everything we needed.
Airbnb
beautiful home, highly recommend for a quick family beach vacay üëå
Airbnb
Great location very close to beach and plenty of space
Airbnb
Great location and house in 30A, the walk to the beach was very easy and the amenities were nice! We enjoyed our stay and would definitely recommend!
Airbnb
This was the perfect family-friendly spot. The host thoughtfully provided books for our stay, making the stay even more memorable.”
Perfect house in a perfect private location
Vrbo
We decided last minute to have a get away. We found this hole on a whim. We loved it ! We have already booked it again!
Vrbo
Vrbo
We enjoyed our stay!
Airbnb
Google
Winter’s End is a great property. The location and amenities are fantastic. In addition we ad the best property management company ever to work with in Oversee.
Google
We had a wonderful experience at our Winter’s End home that was overseen by Oversee. Quick communication regarding any needs that arise and very cleanly!
Vrbo
We had such an unbelievable time on this trip. The house was amazing and the property management team was super responsive to all asks and questions. I highly recommend this stay and we will definitely be coming back in the near future.
Airbnb
Airbnb
The home was exactly as described. Super comfortable furniture and beds! Very clean. The hosts were quick to respond, helpful and friendly with any questions we had. The location for walking to the beach the square to eat, etc was great. We did a lot of biking and walking. Great also that bikes and 4 seater golf cart are provided. Definitely will rent this home again when we are back in the area!!
Airbnb
Airbnb
The house was very spacious and well stocked. The pool was very clean. Easy walk to the beach and golf cart and bikes were an added bonus. Had a wonderful stay.
Vrbo
Absolutely love this house! It was our second time staying in it and we love the location! The house is beautiful and well kept up with. It’s so nice having a private pool to be able to relax in after the beach:) will continue to return!
Vrbo
Perfect size pool. Close to beach. Quiet road. Came with everything we need. We will be back!
Airbnb
We loved our stay! The private saltwater pool was amazing to relax at when you didn’t feel like walking down the street to the beach. The home itself was beautiful, roomy, and comfortable. Not to mention the gold cart and bikes that come with the rental that make the trip into town so quick and easy!
Vrbo
Place was as advertised pool was very nice and inside had everything thing you could need. Beds we’re comfortable and having a golf cart made a big difference when it came time to go out and eat. Close to beach if you want to go. Would highly recommend this place.
Airbnb
The home felt very comfortable and had wonderful amenities. It was like it’s own little oasis and so close to the beach!
Vrbo
I’ll rent this specific home again in the future. It’s location is impeccable (steps from beach access), and it has all the amenities one could ask for. Beautiful place. Property management responded to any and all of my needs and questions. This is short and sweet but not much else needs to be said. Incredible home.
Vrbo
I really can’t recommend this property enough! It’s gorgeous and close to everything but without the extra noise! Customer service with the host was amazing. Very clean and the pool was an absolute perfect amenity for after the beach! We will be back soon!
Oversee
The photos of Winter’s End do not do it justice! We had three families stay comfortably in this home and found the setup to be PERFECT for the kids and toddlers! Having the pool in the center of the home made for easy entertainment and relaxing without ever having to leave home. The golf cart and bikes made getting to the beach super convenient. The location of this home is minutes away from great shopping and dining. There aren’t enough words to describe how great our stay was! We can’t wait to go back!!
Oversee
The house was amazing. It had everything we needed for our stay and the kids loved the outdoor areas. I would definitely rent this house again.
Oversee
2 couples stayed at this great vacation house that offered exactly what we were looking for. Highly recommend this house.
Oversee
This beautiful home has everything you could ask for. The small pool is perfect for the little ones, the outside shower is private and makes getting the sand off easy. The kitchen is fully stocked with utensils, a gas range, 2 sinks and 2 dishwashers. 3 showers (2 down 1 up) are roomy and wonderful. The washer and dryer are big and so useful! There are games, books and puzzles, plenty to keep everyone happy. Bicycles and golf cart are great – and it is an easy walk to the beach should you choose.
Host Family
Diamond Office at Sunnyside
Office location:
Diamond Office at Sunnyside, Florida
Contact Diamond Office at Sunnyside
Winter's End
Santa Rosa Beach - Sleeps 12
4 bedrooms - 6 beds - 3 baths
Prices include all fees and taxes