Winter's End
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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.
Highlights:
📍 Seagrove
🏖️ .4 miles to San Juan Public Beach Access
🛌 4 bedroom, 3 bath
👙 Large, saltwater, private pool! (optional heat)
🛺 Golf cart!
🍤 Gas grill
🚲 4 bikes! Explore Seagrove, Seaside, and WaterColor.
🦞 4-star restaurants
🛍️ Boutiques
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. -
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-Main Stage
Seagrove
Live Music
Gentiva Hospice hosts a monthly Grief and Loss Support Group open to anyone in the community who has experienced the loss of a family member or friend, regardless of whether they received hospice care. This supportive gathering offers a safe and compassionate environment for individuals to share, connect, and find comfort among others who understand their experience. The group meets on the second Thursday of each month from 3:00 PM to 4:30 PM at Gentiva Hospice, located at 732 Baldwin Ave, Suite A, DeFuniak Springs, FL 32435. For further details, individuals can contact Chaplain Thom Phillips by phone at 850-951-9849 or via email.
Brunch Buffet with Santa
Seagrove
Family Fun
A fun-filled evening awaits attendees at Beach Camp Brewpub's Trivia Night, starting at 6 PM. Guests are encouraged to bring their friends to test their knowledge while enjoying food, cold drinks, and great company. Whether someone is a trivia professional or simply looking for a few laughs, it offers a perfect way to spend a night by the beach.
Holiday Wine Market
Seagrove
Food & Drink
The Daytrader Tiki Bar & Restaurant announced the return of "Miracle at The Daytrader," celebrating its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, the pop-up will feature elaborate festive décor, whimsical holiday themes, and imaginative Christmas-themed cocktails at the 30A seaside location. The Miracle concept, which started in 2014 in New York City, has grown into a global tradition with over 200 locations worldwide, known for its dazzling decorations, cheerful atmosphere, and collectible holiday glassware. The Daytrader, recently named "Best Cocktail Spot on 30A" in the 2025 Hot Spot Awards and led by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical twist on the holidays. This year's menu includes new drinks like the Dancing Sugarplums and Miracle Mouse, alongside popular returning favorites such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive staples like Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase. From November 17 through December 31, visitors can enjoy a full Christmas experience at Miracle at The Daytrader, combining tiki culture with holiday kitsch. Guests can sip seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric decorations. The Daytrader is open daily from 11 AM to 9 PM and operates on a first-come, first-served basis. As part of its global mission, Miracle will once again donate 10% of all proceeds from select glassware sales (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a nonprofit dedicated to preventing blindness and restoring sight worldwide.
Russ Whitten-Lakeside
Seagrove
Live Music
Salt Rock Revival, a classic rock and jams duo, performed free live music brought by local artists.
Dueling Pianos-Main Stage
Seagrove
Live Music
The business hosts a monthly local’s weekend where locals and snowbirds receive a 20% discount on classes. This offer is available during the second Saturday and Sunday of every month. Interested participants are encouraged to call 850-231-0544 to reserve a class.
David Martin-Lakeside Brunch
Seagrove
Live Music
The Daytrader Tiki Bar & Restaurant announced the return of Miracle at The Daytrader, marking its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, Miracle at The Daytrader will feature elaborate festive décor, nostalgic holiday themes, and unique Christmas-themed cocktails at the popular seaside destination on 30A. The Miracle concept originated in 2014 in New York City and has since grown to over 200 locations globally, spanning the United States, Canada, Europe, Asia, and Central America. The pop-up is recognized worldwide for its spectacular decorations, playful holiday spirit, and collectible seasonal glassware. The Daytrader, recently honored with Best Cocktail Spot on 30A in the 2025 Hot Spot Awards and overseen by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical interpretation of the holidays. This year’s drink menu includes new creations like the Dancing Sugarplums and Miracle Mouse, alongside favorite returning cocktails such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive items like the Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase. From November 17 through December 31, both locals and visitors can visit Miracle at The Daytrader for a complete Christmas experience that merges tiki culture with holiday kitsch. Guests can enjoy seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric décor, offering a holiday blend unique to Miracle. The Daytrader operates daily from 11 AM to 9 PM, accommodating guests on a first-come, first-served basis. In line with its global mission, Miracle will again contribute 10% of the proceeds from sales of specific glassware (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a non-profit organization dedicated to preventing blindness and restoring sight globally.
Russ-Main Stage
Seagrove
Live Music
The event features Russ performing live on the Main Stage from 6 to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
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.
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live between 7 PM and 10 PM.
Russ Whitten-Lakeside
Seagrove
Live Music
Russ Whitten-Lakeside will be performing live from 4:30 PM to 8:30 PM.
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live from 7:30 PM to 10:30 PM.
Brunch Buffet with Santa
Seagrove
Family Fun
The event offers family friendly fun for everyone. Santa Claus, Mrs. Claus, and his elves will be visiting the location. Reservations are encouraged, and the brunch menu is available on their website.
Holiday Wine Market
Seagrove
Markets & Shopping
A holiday wine market is being held from 12-3 PM.
Christmas Carolers
Seagrove
Live Music
A Christmas Carolers event will be taking place from 4:30 PM to 7:30 PM.
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos performs live on the main stage from 7:30 PM to 10:30 PM.
David Martin-Lakeside Brunch
Seagrove
Live Music
David Martin will be performing live from 10 AM to 2 PM.
Need – Main Stage
Seagrove
Live Music
The band Catch Need performs live on the Main Stage from 6 to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Fri, December 12
Dueling Pianos-Main Stage
Seagrove
Live Music
Gentiva Hospice hosts a monthly Grief and Loss Support Group open to anyone in the community who has experienced the loss of a family member or friend, regardless of whether they received hospice care. This supportive gathering offers a safe and compassionate environment for individuals to share, connect, and find comfort among others who understand their experience. The group meets on the second Thursday of each month from 3:00 PM to 4:30 PM at Gentiva Hospice, located at 732 Baldwin Ave, Suite A, DeFuniak Springs, FL 32435. For further details, individuals can contact Chaplain Thom Phillips by phone at 850-951-9849 or via email.
Sat, December 13
Brunch Buffet with Santa
Seagrove
Family Fun
A fun-filled evening awaits attendees at Beach Camp Brewpub’s Trivia Night, starting at 6 PM. Guests are encouraged to bring their friends to test their knowledge while enjoying food, cold drinks, and great company. Whether someone is a trivia professional or simply looking for a few laughs, it offers a perfect way to spend a night by the beach.
Sat, December 13
Holiday Wine Market
Seagrove
Food & Drink
The Daytrader Tiki Bar & Restaurant announced the return of “Miracle at The Daytrader,” celebrating its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, the pop-up will feature elaborate festive décor, whimsical holiday themes, and imaginative Christmas-themed cocktails at the 30A seaside location.
The Miracle concept, which started in 2014 in New York City, has grown into a global tradition with over 200 locations worldwide, known for its dazzling decorations, cheerful atmosphere, and collectible holiday glassware. The Daytrader, recently named “Best Cocktail Spot on 30A” in the 2025 Hot Spot Awards and led by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical twist on the holidays. This year’s menu includes new drinks like the Dancing Sugarplums and Miracle Mouse, alongside popular returning favorites such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive staples like Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase.
From November 17 through December 31, visitors can enjoy a full Christmas experience at Miracle at The Daytrader, combining tiki culture with holiday kitsch. Guests can sip seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric decorations. The Daytrader is open daily from 11 AM to 9 PM and operates on a first-come, first-served basis.
As part of its global mission, Miracle will once again donate 10% of all proceeds from select glassware sales (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a nonprofit dedicated to preventing blindness and restoring sight worldwide.
Sat, December 13
Russ Whitten-Lakeside
Seagrove
Live Music
Salt Rock Revival, a classic rock and jams duo, performed free live music brought by local artists.
Sat, December 13
Dueling Pianos-Main Stage
Seagrove
Live Music
The business hosts a monthly local’s weekend where locals and snowbirds receive a 20% discount on classes. This offer is available during the second Saturday and Sunday of every month. Interested participants are encouraged to call 850-231-0544 to reserve a class.
Sun, December 14
David Martin-Lakeside Brunch
Seagrove
Live Music
The Daytrader Tiki Bar & Restaurant announced the return of Miracle at The Daytrader, marking its third holiday season as the sole Miracle Pop-Up location in Northwest Florida. Beginning Monday, November 17, Miracle at The Daytrader will feature elaborate festive décor, nostalgic holiday themes, and unique Christmas-themed cocktails at the popular seaside destination on 30A.
The Miracle concept originated in 2014 in New York City and has since grown to over 200 locations globally, spanning the United States, Canada, Europe, Asia, and Central America. The pop-up is recognized worldwide for its spectacular decorations, playful holiday spirit, and collectible seasonal glassware.
The Daytrader, recently honored with Best Cocktail Spot on 30A in the 2025 Hot Spot Awards and overseen by James Beard Award semi-finalist Chef Nikhil Abuvala, offers a tropical interpretation of the holidays. This year’s drink menu includes new creations like the Dancing Sugarplums and Miracle Mouse, alongside favorite returning cocktails such as the Christmapolitan, Snowball Old-Fashioned, and Jingle Balls Nog. Limited-edition glassware, including festive items like the Santa’s Head, SanTaRex, and Christmas Unicorn, along with new seasonal designs, will be available for purchase.
From November 17 through December 31, both locals and visitors can visit Miracle at The Daytrader for a complete Christmas experience that merges tiki culture with holiday kitsch. Guests can enjoy seasonal cocktails under a thatched roof, surrounded by twinkling lights and eccentric décor, offering a holiday blend unique to Miracle. The Daytrader operates daily from 11 AM to 9 PM, accommodating guests on a first-come, first-served basis.
In line with its global mission, Miracle will again contribute 10% of the proceeds from sales of specific glassware (including Santa Pants, Christmas Carol Barrel, and Santa Heads) to the Seva Foundation, a non-profit organization dedicated to preventing blindness and restoring sight globally.
Sun, December 14
Russ-Main Stage
Seagrove
Live Music
The event features Russ performing live on the Main Stage from 6 to 9 PM.
Mon, December 15
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Tue, December 16
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier will be performing live on the Main Stage from 6:30 PM to 9:30 PM.
Wed, December 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.
Thu, December 18
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live between 7 PM and 10 PM.
Fri, December 19
Russ Whitten-Lakeside
Seagrove
Live Music
Russ Whitten-Lakeside will be performing live from 4:30 PM to 8:30 PM.
Fri, December 19
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos-Main Stage is scheduled to perform live from 7:30 PM to 10:30 PM.
Sat, December 20
Brunch Buffet with Santa
Seagrove
Family Fun
The event offers family friendly fun for everyone. Santa Claus, Mrs. Claus, and his elves will be visiting the location. Reservations are encouraged, and the brunch menu is available on their website.
Sat, December 20
Holiday Wine Market
Seagrove
Markets & Shopping
A holiday wine market is being held from 12-3 PM.
Sat, December 20
Christmas Carolers
Seagrove
Live Music
A Christmas Carolers event will be taking place from 4:30 PM to 7:30 PM.
Sat, December 20
Dueling Pianos-Main Stage
Seagrove
Live Music
Dueling Pianos performs live on the main stage from 7:30 PM to 10:30 PM.
Sun, December 21
David Martin-Lakeside Brunch
Seagrove
Live Music
David Martin will be performing live from 10 AM to 2 PM.
Sun, December 21
Need – Main Stage
Seagrove
Live Music
The band Catch Need performs live on the Main Stage from 6 to 9 PM.
Mon, December 22
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier can be seen live on the Main Stage from 6:30 PM to 9:30 PM.
Reviews - 20
Google
Definitely will be coming back.
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