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We look forward to booking your Seasider Experience.



Spring Break
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Fourth Of July
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Fall Break
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Summer 2019
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Bedrooms: 2 | Bathrooms: 2.5 | Max Occ: 4          Virtual Tour

Address: 759 Forest Street

Pets Allowed

*Note: Published rates are exclusive of taxes and fees and are subject to change at anytime.


Bright and cheery Leeward creates a colorful backdrop for your beach vacation, with an impressive trio of porches for multiple floors of outdoor living, dining and views. Welcomed by a delightful front porch, complete with rockers, the home immediately creates an easy-going, relaxed vibe for all who visit.

Two queen-sized bedrooms and private baths make up the first level of the home, accented by cheerful and complimentary colors, from the brightly hued walls to the clean white accents. Meanwhile, wooden steps wind up to the main living level of the home, with its comfortable and quaint living room, framed by an infusion of plenty of natural light.

A cozy kitchen offers up just the right amount of space for guests, large enough to prepare a meal, yet efficient enough to stay tidy. The nearby dining room, meanwhile, allows space for a casual meal, overlooking some of the best extra features of the home. For additional space, open up the glass doors to a delightful outdoor dining area, with tree topped scenery providing both views and privacy.

For some of the most exciting views, though, climb up the unique ladder stairway to your own furnished tower porch. Whether sipping on your morning coffee high above the rest or watching a magical sunset at the end of your refreshing day, this versatile space helps push your Seaside vacation to new heights, delivering just the right mix of relaxation and comfort.

With a convenient location not far from swimming and recreation, Leeward presents an exceptional choice for guests, exceeding your expectations as it rises to the top of your list of vacation cottages in sunny Seaside, Florida.  Must be 25 years of age to rent and sign registration.  

*A non-refundable pet fee of $275.00 (plus sales tax) is required.  The online quote does not reflect the additional charge.  The additional fee of $275 will be added to your reservation and you will receive an updated receipt confirming your reservation and the total charge including the pet fee. 

* 5-night minimum Spring Break and Summer | 3 night minimum in Fall.


  •  Located on the west side of Seaside
  •  Newly redecorated
  •  968 sq. ft.
  •  Tower offering spectacular views
  •  Pole mounted grill
  •  Pet friendly
  •  Washer & Dryer
  •  Access to the town amenities, 3 swimming pools, 6 tennis courts (court fees apply), and a fitness center
  •  Welcome tote with 2 beach towels and a complimentary bottle of wine  
  •  Personalized service throughout your stay

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Kathy C.     Review Date: December 2017

Everything at Leeward was as represented on the listing. One bonus is that the house has 2 1/2 baths instead of just 2, with the half bath being on the floor with the kitchen, LR and DR. The decks are very nice and the house is well-maintained. I booked at the last minute and management company was able to handle that and get all the information I needed to me in a timely fashion.

Brent L     Review Date: June 2018

First time to go through Homeowners and was a great experience. We have been to Seaside several times over the past 15 years. First time to stay at Leeward. Very nice and clean.

Sherri B     Review Date: July 2018

Great we already booked for 2019

Dianne H     Review Date: July 2018

Homeowners Collection was such a great company to work with! Communication was perfect and the personal service was on point. Really liked how they met us at the property when we arrived to go over details of the house. The house was fully stocked and met our needs. The living room furniture wasn’t very comfortable but otherwise the house was perfect for our needs.

Amanda B     Review Date: July 2018

We really enjoyed our stay at Leeward and all our interactions with the Homeowners Collection staff!

Amy B     Review Date: September 2018

A beach cottage to take you to a place that you forget your worries, and all that matters is a cozy porch where you will drink your coffee, a rooftop to admire the view and a cozy living room to have a nightcap at the end of a beautiful Seaside day. Three girls got away for a girls weekend and Leeward, with its beach vibe and tasteful decor was the perfect escape. The office staff, Rhonda, were wonderful, quick to return phone calls and so helpful. The welcome basket had two of lifes essentials..Coffee and wine! The property was extremely clean. The Leeward AND Homeowners collection will be our pick for our next girls weekend getaway. Thank you Homeowners collection!!!!