Bailey Hall holiday rentals

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October 2025

November 2025

Holiday rentals with weekly discounts - Bailey Hall

Showing deals for:9 Jan - 16 Jan

Exceptional

(67 reviews)

Siesta Zen – 2BR Steps to Siesta Key Beach & Village

Siesta Key, FL

7% off

for 7 nights, 1 home

AU$543 per night

includes taxes & fees

Exceptional

(21 reviews)

Private Siesta Key Home with Great Location walk to Village and Beach!

Siesta Key, FL

8% off

for 7 nights, 1 home

AU$1,672 per night

includes taxes & fees

Plenty of lounge chairs and shade if you choose.

Exceptional

(112 reviews)

LuLu Kemp Ridley | Heated Pool | BBQ | 4 Min Walk to Beach | Near Shops | Downstairs

Siesta Key, FL

7% off

for 7 nights, 1 apartment

AU$677 per night

includes taxes & fees

Wonderful

(88 reviews)

Beautiful 2BR 2BA Home with Private Pool & Jacuzzi - Includes Pool Table

Siesta Key, FL

8% off

for 7 nights, 1 home

AU$704 per night

includes taxes & fees

Leatherback's living room with a large flatscreen TV for movie nights and popcorn.

Exceptional

(135 reviews)

$185 Free Activities Daily, LuLu's Leatherback Near Beach/Village, Heated Pool, Beach Gear Included

Siesta Key, FL

8% off

for 7 nights, 1 apartment

AU$817 per night

includes taxes & fees

Aerial view of pool and mural wall at LuLu's Key House.

Exceptional

(106 reviews)

Heart of Siesta Key Village, Walk to Beach, Heated Pool, Comes with Beach Gear!

Siesta Key, FL

8% off

for 7 nights, 1 apartment

AU$614 per night

includes taxes & fees

Exceptional

(137 reviews)

LuLu's Loggerhead Renovated | Walk to Siesta Key Beach | Heated Pool | Beach Gear Included!

Siesta Key, FL

8% off

for 7 nights, 1 apartment

AU$798 per night

includes taxes & fees

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Find the best place to stay - Bailey Hall

Shell-Abrate Good Times - By Siesta Key Luxury Rental Properties

Premier Host

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Sleeps 14 · 6 bedrooms · 6+ bathrooms

Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!

Sleeps 6 · 2 bedrooms · 2 bathrooms

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, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value