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Book Online or call HomeAway Booking Assistance 888-640-7927

Windsor by the Sea, 5 Bedrooms, Sleeps 12, Beach Front, Private Pool, Cinnamon Beach

Bedrooms 5
Property type house
Minimum Stay 1 - 7 nights


About the property

5 Bedrooms, 5 Baths, Sleeps 12

When only the best will do, Windsor by the Sea is an ideal choice. An oceanfront house in the gated Cinnamon Beach community, it includes 5 bedrooms to accommodate up to 12 guests, making it well suited for one or several families. In addition to a wealth of space, the house has all the amenities you would expect of a world-class resort--and more. An amazing private pool and hot tub, game room, pool table, gourmet kitchen, fully equipped bar, multiple balconies looking out to the Atlantic ocean, even an elevator: So much luxury awaits! Take a dip in the new private pool with hot tub. Enjoy the new summer kitchen and fire pit after a day at the beach. (Please note that the private pool at the house is not heated. The fire pit at Windsor By the Sea CANNOT be used until further notice due to the Flagler County burn ban).

Let’s start at the top, the 4th floor, home to the sumptuous master suite. Actually, it’s more like a self-contained apartment. There’s the bedroom itself, complete with king-size bed, 50” HDTV, and iHome clock radio, and an equally lavish bathroom with both soaking Jacuzzi tub and walk-in shower with eleven shower heads. There’s a kitchenette as well. No need to head downstairs to the kitchen to fix yourself breakfast or a late-night snack; the kitchenette is equipped with microwave, fridge, blender, toaster, coffee maker, and of course tableware. Once you’ve prepared your meal or drink, you can savor it on the adjacent balcony.

Hopefully, you won’t have to work on your vacation. If you do, though, the 4th-floor office is a lovely place to hunker down. Look out at a breathtaking view of the ocean while you handle your business. It’s furnished with a 40” TV and a pull-out twin sofa bed, should you want to mix some relaxation with your business.

The 3rd floor is home to the open living room, dining area, and kitchen. The furnishings are nothing less than stunning, but they’re also wonderfully comfortable. With 2 sofas, 2 armchairs, and 2 ottomans, the living room offers plenty of seating for everyone to gather and catch a favorite movie or the big game on the 65” 4K HDTV with Blu-ray player.

Likewise, the mahogany dining table easily seats 10, with room for several more at the gleaming granite breakfast bar. If you’d prefer to dine alfresco, there are dining areas on both the 3rd-floor and 2nd-floor balconies. What’s more, the 3rd-floor balcony has a built-in grill, so that you can cook as well as eat while listening to the waves rolling onto the beach.

Then again, once you see the huge, spectacularly equipped kitchen, you may never want to cook anywhere else ever again. Stainless-steel appliances 2 wine coolers, 2 sinks, multiple counters, cookware, and tableware--the kitchen has it all, and it’s all of the exceptional quality.

There’s a bedroom on the 3rd floor as well. With a queen-size bed and a trundle bed, it’s ideal for a couple with a young child or for a couple of kids looking forward to a pajama party every night.

The centerpiece of the 2nd floor is the huge game room, which easily rivals any resort clubhouse. Pool tables, 4 TVs, 4 roomy leather armchairs… and let’s not forget the bar, complete with fridge, 2 wine coolers, blenders, and coffee pot. Looking for a quiet get-a-way to read a good book, go out to the 2nd-floor side balcony with ocean views.

A 3rd bedroom is on the 2nd floor which has an adjoining balcony with new railings, furnished with a king-size bed and a 32” HDTV. The remaining 2 bedrooms are on the 1st floor. Each has a 32” HDTV and an iHome radio. One includes a lofty queen-size bed; the other has a queen-size bed, a crib, and a changing room--after all, even babies deserve to vacation in style!

As if this weren't enough, when you stay at Windsor by the Sea you can take advantage of the amenities of Cinnamon Beach Club, just a few minutes’ walk away. Swim in the 2 heated community pools, work out in the fitness center, take the kids to the “splash zone,” grab a snack in the café, play foosball and air hockey in the clubhouse--and of course stroll on one of the boardwalks to the private beach.

Surfing in the ocean, swimming in the pool, gathering shells on the beach, soaking in the hot tub, chilling on the balcony with family and friends: At Windsor by the Sea, you can do it all, in the utmost of style. Treat yourself to an extraordinary experience; book your stay today.

More Details

Property Manager
Member since: 1996
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
April 26, 2018

About VTrips

Hi! My name is Steve Milo and I started Vacation Rental Pros in 2006. Our family stays in vacation rental homes whenever we travel, both domestically and abroad! I own several vacation homes and listen carefully to all our guests' feedback. Our greatest compliment is when folks refer Vacation Rental Pros to their friends and relatives. We now manage over 1,800 properties in Florida, Tennessee and South Carolina. We have homes in Ft. Myers Beach, Orlando, St. Augustine Beach, Daytona Beach, Palm Coast, Ponte Vedra Beach, Hilton Head and Gatlinburg. We booked over 15,000 rentals and received over 5,000 guest reviews in 2016. Please call if you need help booking your dream vacation!


Palm Coast House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 10:00 AM
  • Max. occupancy: 12
  • Min. age of primary renter: 25
  • Children welcome
  • Parties/events not allowed
  • Pets not allowed
  • Non smoking only
Location Type:
  • Beach View
  • Beachfront
  • Ocean View
  • Oceanfront
  • Water View
  • Waterfront
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Spa
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Clothes Dryer
  • Elevator
  • Fitness Room / Equipment
  • Heating
  • Internet
  • Linens Provided
  • Living Room
  • Parking
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • Dining Room
  • 5 Bathrooms
  • 5 Bedrooms, Sleeps 12
  • Bedroom # 1 (1 King), Bedroom # 2 (1 Queen, 1 Trundle), Bedroom # 3 (1 King), Bedroom # 4 (1 Queen), Bedroom # 5 (1 Queen)
  • DVD Player
  • Pool Table
  • Satellite / Cable
  • Television
  • Balcony
  • Bicycles
  • Boat
  • Deck / Patio
  • Golf
  • Long-term Renters Welcome
Pool / Spa:
  • Communal Pool
  • Hot Tub
  • Private Pool
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • recreation center
  • restaurants
  • synagogues
  • water parks
Leisure Activities:
  • boating
  • miniature golf
  • outlet shopping
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • jet skiing
  • kayaking
  • parasailing
  • pier fishing
  • surf fishing
  • surfing
  • swimming


3.2/5 -
(9 traveler reviews)

33% Complete
11% Complete
22% Complete
11% Complete
22% Complete
Windsor by the Sea, 5 Bedrooms, Sleeps 12, Beach Front, Private Pool, Cinnamon Beach
average rating of 3.2222223 based on 9 reviews

Beautiful home but major management issues

  • 2 of 5

The home is beautiful.

However, there were several issues:

1. Arrival was a disaster:

We registered ahead of time to enter the gated community. Security handed our registration back to us and told us that our home was already rented to someone else. We were unable to get to the home.

We had to drive back over the bridge to the V Trips office. We were told that they were closed but they would make an exception and let us in. Turns out they registered us under the wrong home. The entire ordeal took about 2 hours. Security told us that this company was known for "messing up the registration".


Our boardwalk was closed and under construction. We had to walk down the street to the clubhouse for beach access.


The elevator did not work. It was supposedly repaired twice while we were there but it didn't work. It intermittently hummed and ran up and down all 4 was difficult to sleep at night with all of he noise.


Hotdogs and salsa covered in thick mold. It wasn't pretty.


We had to take rope and tie it around the outside doors for 2 of the bedrooms.


Looked like they were just thrown back into the cupboards after use.

7. SPA Heater was slow

It took about 8 hours for it to warm up


Thank master bedroom had dirty, smelly sheets on the bed.

9. 2 of our family members arrived Wednesday night. They were registered ahead of time of these guests was 11 years old and security wouldn't let her through because they didn't have her name but did have her mother's.

We had given all of the necessary information directly to your person and it was still done incorrectly.

Your office was closed when they arrived and we were finally connected with someone who helped us after sitting at the gate for almost an hour. We got to know George at security quite well during our trip.

10. Old cigar buts on the patio in the empty pots

11. Outdoor kitchen on the third floor was completely rusted.

12. A house of this caliber should provide at least 1 hair dryer and more than 2 bathtowels per bathroom.

The house and beach are absolutely beautiful but we do feel that the management could be much better.


  • Submitted: Apr 6, 2018
  • Stayed: March 2018
  • Source: VRBO, from HomeAway
Owner's Response: Deborah, We apologize for any distress that you and your family faced during your stay at Windsor by the Sea. We are remorseful for the mishap regarding your arrival. We were unaware that the boardwalk was under construction and are embarrassed about the upkeep of the house. We have made the necessary changes and updates in our system and are working to better rectify the situation in the future. We appreciate the feedback and hope that you continue to book with us.
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0 0

Disappointed in the condition of the property!!

  • 1 of 5

Our first impression of the property was very good. However, we quickly noticed that the exterior porches and furniture were filthy and covered with mold. A walk onto the MB patio required us to scrub the black dirt off of our feet!!!! Most of the TV remotes were missing batteries and did not work. The pool was very dirty on arrival and we could not work the hot tub or the filter for most of the week. Maintenance was very slow to respond to our requests. When they finally did arrive, they informed us that the pool gets cleaned on Tuesday (Not a great plan when rentals start on Saturday!!!) and they provided batteries for the remotes. The Master BR TV did not work also. Maintenance just said that the TV was "tempermental" but that they would put in a repair ticket. Never heard back on that so no TV in the MB. Maintenance was very quick to respond on one issue... when one of our guests turned the air below 72 degrees. Maintenance was quick to warn us that we would be assessed a fine of $150 if it happened again. Overall, I would never rent this property again. However, I would return to Cinnamon Beach and rent a different property.

  • Submitted: Aug 11, 2017
  • Stayed: July 2017
  • Source: HomeAway
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7 0

Great pool and hot tub on the ocean! Disappointed in house!

  • 1 of 5

However we were very disappointed that there were a lot of issues with the house. The grills didn't work. No knobs on either one, my son almost got burned trying to get one lit! We were going to cookout for Memorial Day and have a fun party at the pool but everyone was up in a tizzy because no way to grill food. It was stressful and late when we finally ate supper! When I called maintenance they said they could come out the next morning. A lot of good that did us! By the way they did not come the next morning. Another disappointment was the dishwasher didn't clean the dishes. Every night that we cooked, and also breakfast we had to wash the dishes! No one wants to wash dishes on their vacation! One of the steps going to level 1 was broken and we had to be real careful not to fall down steps. There were light bulbs that didn't work and shower doors that were loose. Not to mention mold in bathroom shower! The house really needed a lot of maintenance. Also, part of the wood door at end of dock at beach was broken off hinges and laying in the grass!

Very disappointed for the amount of money we paid!

  • Submitted: Jun 5, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
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5 1

Beautiful House! Great location! Poor customer service from Vacation Rentals Pros

  • 3 of 5

What a house!!! We loved everything about the house, except for the pool not being is a gas heater, seriously? Why not heat the pool? Top of the line furnishing, TV's, game room, master bathroom, everything you could wish for!!! Now why the 3 stars... The pool is not heated, and the housekeeping/maintenance not responding. To get a hold of maintenance we had to call and pretend to be interested in renting. When we asked for the housekeeping or maintenance department, we had to leave a message that was never answered. We loved the house did not appreciate the lack of response from Vacation Rental Pro.

  • Submitted: Apr 4, 2017
  • Stayed: March 2017
  • Source: VRBO, from HomeAway
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2 0

Great potential, but disappointing maintenance

  • 3 of 5

Our family is currently staying at this house. There is no direct beach access at this time as the walkway to the beach has not been repaired since the hurricane in early October. We were disappointed about this as we were told it would be repaired by early November. There is beach access about the distance of 20 houses away. There is other damage that has not been repaired to the screens on the porches. Some are missing and some are torn. The overall maintenance of the exterior was neglected upon our arrival. The oceanfront porches had dirty floors and the cushions on the furniture were extremely dirty and with mold. 10 days after our arrival after persistent calls to the management company , we were able to have the porches, furniture and cushions power-washed. After 2 more days we were finally able to sit on the porches. Windows really need cleaning. There is quite a bit of construction around the house, but except for one day the noise has not really been an issue. 5 of the televisions do not work and we have had 3 service calls to try to deal with this. Overall the interior is in good condition and was clean, but there are 2 layers of slip covers on the living room furniture. This house could be great, which is why the rating is not lower.

  • Submitted: Dec 23, 2016
  • Stayed: December 2016
  • Source: VRBO, from HomeAway
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10 0

Wonderful House

  • 5 of 5

Wonderful house for our family. Master suite is awesome. We will have our 3rd family vacation at Windsor by the Sea this year.

  • Submitted: Dec 14, 2016
  • Stayed: April 2016
  • Source: VRBO, from HomeAway
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0 0


Car: necessary


Rates & Availability

Taxes and fees are additional


  • Rates shown above do not include taxes and fees

    Booking Fee: 8%
    Charge basis: AD
    For stays between 1 and 365 nights

    Cleaning Fee: $450
    Charge basis: STAY
    For stays between 1 and 365 nights

    Damage Protection: $295
    Charge basis: STAY
    For stays between 1 and 365 nights

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