Bailey Hall holiday lettings

We found 518 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.

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Find the best place to stay - Bailey Hall

Sunset Gazers Paradise - Resort Pool - Mini Golf

• Address: Siesta Key, FL
• Guest rating: 10/10 (Exceptional, 34 reviews)

Premier Host

Sleeps 12 · 5 bedrooms · 5+ bathrooms

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

• Address: Siesta Key, FL
• Guest rating: 9.8/10 (Exceptional, 101 reviews)

Premier Host

Sleeps 10 · 3 bedrooms · 3 bathrooms

Siesta Key APT On OceanW/FREE WIFI, BEACH AMENTITIES, ONSITE MANAGER, &LAUNDRY

• Address: Siesta Key, FL
• Guest rating: 8.4/10 (Very good, 15 reviews)

Sleeps 4 · 1 bedroom · 1 bathroom

Beautiful,Cozy 3Bed/2 Siesta Key home on Ocean blvd, close to village, beaches,

• Address: Siesta Key, FL
• Guest rating: 8.8/10 (Excellent, 36 reviews)

Sleeps 9 · 2 bedrooms · 2 bathrooms

Waterfront KEY home w/ Pool, HotTub, mins to beach

• Address: Siesta Key, FL
• Guest rating: 9.2/10 (Wonderful, 10 reviews)

Premier Host

Sleeps 16 · 5 bedrooms · 3 bathrooms

Resort style amenities and convenient to The Village shops and restaurants!

• Address: Sarasota, FL
• Guest rating: 10/10 (Exceptional, 35 reviews)

Sleeps 8 · 4 bedrooms · 3 bathrooms