Bailey Hall holiday lettings

We found 506 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Bailey Hall that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, including air conditioning and Wi-Fi. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Find the best place to stay - Bailey Hall

Image of Gertrude Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key
Premier Host

Gertrude Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key

Sleeps 10 · 3 bedrooms · 3 bathrooms
9.8 out of 10
exceptional
(101 reviews)
More information about Gertrude Siesta | Private Patios, Beach & Village, 100 steps to Best Views on Siesta Key, opens in a new tab

Top rated rentals - Bailey Hall

Interior
Premier Host
Very well appointed property in an excellent location.
10.0 out of 10, Exceptional, 132 reviews
"We loved the location within walking distance to the lively village and amazing beach. Having a parking slot available at the beach and provision of chairs, shades etc was a real bonus. The Sarasota area also has many activities and sites of interest within a short drive. The property is very well equipped and in excellent condition. Ron was also an extremely helpful and supportive owner. "
Andrew S.
Andrew S.
Stayed Jul 2017
Beautiful Siesta Key

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value