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. -
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
Dueling Pianos will be performing live from 7 PM to 10 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos is scheduled to perform live from 7 PM to 10 PM.
Bryan Umphy-Main Stage
Seagrove
Live Music
Bryan Umphy can be seen performing live on the Main Stage between 6 and 9 PM.
Bryan Umphy-Main Stage
Seagrove
Live Music
Bryan Umphy-Main Stage is scheduled to perform live from 6-9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen live from 6:30 to 9:30 PM.
30A Singer/Songwriter
Seagrove
Live Music
The 30A Singer/Songwriter event will feature a live performance from 7:00 PM to 10:00 PM.
30A Singer/Songwriter
Seagrove
Live Music
A 30A singer/songwriter will be performing live from 7 PM to 10 PM.
30A Singer/Songwriter
Seagrove
Live Music
The event features a 30A singer/songwriter performing live from 7 PM to 10 PM.
30A Singer/Songwriter
Seagrove
Live Music
A 30A Singer/Songwriter performance will be held live from 7 PM to 10 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is performing live on the Main Stage from 6 PM to 9 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will perform live from 6:30 PM to 9:30 PM.
Dueling Pianos
Seagrove
Live Music
The Dueling Pianos show can be seen live from 7 PM to 10 PM.
Red Shoe Party
Seagrove
Arts & Culture
The Florida Fish House is set to host the Red Shoe Party on Saturday, January 24, 2026. This elegant cocktail-style event supports children in foster care across Okaloosa and Walton Counties. The event is inspired by the iconic red shoes, which symbolize hope, comfort, and belonging. Cocktail attire is encouraged, and guests can participate in the Red Shoe Contest categories: Sportiest, Most Glamorous, and Most Creative. The evening will feature chef-driven small plates, entree stations, desserts, themed cocktails, a silent auction, and meaningful stories highlighting the impact of the cause. Tickets are $150 and are of limited availability. Sponsorship opportunities are also available. More information and tickets can be found at the event's website.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will be performing live from 7 to 10 PM.
Russ Whiten-Main Stage
Seagrove
Live Music
The event features a live performance by Russ Whiten on the Main Stage, scheduled from 6 PM to 9 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs on the Main Stage live from 6:00 PM to 9:00 PM.
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be caught live from 6:30 to 9:30 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will be performing live from 7:00 PM to 10:00 PM.
Dueling Pianos
Seagrove
Live Music
Dueling Pianos performs live from 7 PM to 10 PM.
Fri, January 9
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will be performing live from 7 PM to 10 PM.
Sat, January 10
Dueling Pianos
Seagrove
Live Music
Dueling Pianos is scheduled to perform live from 7 PM to 10 PM.
Sun, January 11
Bryan Umphy-Main Stage
Seagrove
Live Music
Bryan Umphy can be seen performing live on the Main Stage between 6 and 9 PM.
Mon, January 12
Bryan Umphy-Main Stage
Seagrove
Live Music
Bryan Umphy-Main Stage is scheduled to perform live from 6-9 PM.
Tue, January 13
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.
Wed, January 14
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.
Thu, January 15
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be seen live from 6:30 to 9:30 PM.
Fri, January 16
30A Singer/Songwriter
Seagrove
Live Music
The 30A Singer/Songwriter event will feature a live performance from 7:00 PM to 10:00 PM.
Sat, January 17
30A Singer/Songwriter
Seagrove
Live Music
A 30A singer/songwriter will be performing live from 7 PM to 10 PM.
Sun, January 18
30A Singer/Songwriter
Seagrove
Live Music
The event features a 30A singer/songwriter performing live from 7 PM to 10 PM.
Mon, January 19
30A Singer/Songwriter
Seagrove
Live Music
A 30A Singer/Songwriter performance will be held live from 7 PM to 10 PM.
Tue, January 20
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 to 9 PM.
Wed, January 21
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is performing live on the Main Stage from 6 PM to 9 PM.
Thu, January 22
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will perform live from 6:30 PM to 9:30 PM.
Fri, January 23
Dueling Pianos
Seagrove
Live Music
The Dueling Pianos show can be seen live from 7 PM to 10 PM.
Sat, January 24
Red Shoe Party
Seagrove
Arts & Culture
The Florida Fish House is set to host the Red Shoe Party on Saturday, January 24, 2026. This elegant cocktail-style event supports children in foster care across Okaloosa and Walton Counties. The event is inspired by the iconic red shoes, which symbolize hope, comfort, and belonging. Cocktail attire is encouraged, and guests can participate in the Red Shoe Contest categories: Sportiest, Most Glamorous, and Most Creative. The evening will feature chef-driven small plates, entree stations, desserts, themed cocktails, a silent auction, and meaningful stories highlighting the impact of the cause. Tickets are $150 and are of limited availability. Sponsorship opportunities are also available. More information and tickets can be found at the event’s website.
Sat, January 24
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will be performing live from 7 to 10 PM.
Sun, January 25
Russ Whiten-Main Stage
Seagrove
Live Music
The event features a live performance by Russ Whiten on the Main Stage, scheduled from 6 PM to 9 PM.
Tue, January 27
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier performs on the Main Stage live from 6:00 PM to 9:00 PM.
Wed, January 28
Alex Napier-Main Stage
Seagrove
Live Music
Alex Napier is scheduled to perform live on the Main Stage from 6 PM to 9 PM.
Thu, January 29
Dueling Pianos
Seagrove
Live Music
Dueling Pianos can be caught live from 6:30 to 9:30 PM.
Fri, January 30
Dueling Pianos
Seagrove
Live Music
Dueling Pianos will be performing live from 7:00 PM to 10:00 PM.
Sat, January 31
Dueling Pianos
Seagrove
Live Music
Dueling Pianos performs live from 7 PM to 10 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
Prices include all fees and taxes