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Summer 2019
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Luck Of The Draw

Bedrooms: 1 | Bathrooms: 1 | Max Occ: 2          Virtual Tour

Address: 14 Pensacola Street

Pets Not Allowed

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


When a cozy space is all you need, the ‘Luck of the Draw’ cottage provides the ideal setting for a vacation to quaint Seaside. This intimate abode delivers the perfect fit for a couple’s getaway, where everything is equipped to comfortably house two, with just the right amount of living space. A short stroll from the beach, the ‘Luck of the Draw’ cottage rewards its visitors with a winning combination of location matched with charming attributes.

The guest house to the nearby ‘Play Therapy’ cottage, the brightly hued exterior of ‘Luck of the Draw’ blends traditional beach-style living with the convenience of your own personal space. The bright pink cottage opens up to more natural hues inside, where a rustic wood ceiling tops a main living space equipped with a warm and comfortable living room, kitchen and accompanying dining area, all infused with plenty of natural light from the many glass doors and windows. As well, the cottage benefits from the advantage of new flooring.

A spiral staircase winds to the second level of the cottage where the queen-sized master suite comes into view. A charming four-poster bed fills the space, along with a television and night table. Wainscot paneling provides additional depth to the room, while a shower in the master bath supplies extra convenience.

A fanciful deck leads off the master suite with room for a small seating area, perfect for grabbing a cup of coffee while the sun comes up or simply enjoying the sensational views.

From its white picket fence and lushly landscaped property to its vibrantly colored exterior and peaceful interior, there’s plenty to enjoy about a vacation within the admirable ‘Luck of the Draw’ cottage.  Must be 25 years of age to rent and sign registration.  

* 3-night minimum year-round.


  •  Views of the Gulf
  •  Located on the west side of Seaside
  •  420 sq. ft.
  •  Steps away from beach access
  •  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
  • Starter amenities provided

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Sue B.     Review Date: May 2016

Great location. Cute place. Very comfortable. We LOVE Seaside. Service was great!

Georgia P.     Review Date: March 2015

This cottage had an amazing view of the gulf from the bedroom that we were not expecting. We were able to keep the doors open during the evening and let the breeze roll in. The location was super close to beach access and super close to town square. Only thing missing for us was a TV downstairs.

Mark B     Review Date: June 2018

Amazing location right across from a beach pavilion walk way. Nice front porch with fenced in front yard. Small kitchen was well stocked. We enjoyed our stay, but bathroom needs updating and was not clean. Small spiral staircase was a bit difficult when traveling up and down. We are fit and in our 40’s, but still challenging. New patio chairs would be nice. Location is hard to beat and was well priced.

Nicole D     Review Date: July 2018

This is our 2nd time to stay with a Homeowners Rental. Top notch management company! Luck of the Draw is adorable. Perfect for two people! We had a mother daughter stay and enjoyed it tremendously! Oh, add a mirror somewhere on a wall outside of the bathroom so another person can get ready. =)