Bay Island holiday lettings
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Holiday rentals with weekly discounts - Bay Island
Showing deals for:7 Nov - 14 Nov
Image gallery for Spacious salt water pool home minutes from Siesta Key & downtown
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Spacious salt water pool home minutes from Siesta Key & downtown
Sarasota, FL
6% off
Price is £1,305
£1,305
£186 per night
includes taxes & fees
Image gallery for Enjoy a new remodeled house minutes away from Anna Maria Island
8.68.6 out of 10 rating
Excellent
(8 reviews)
Enjoy a new remodeled house minutes away from Anna Maria Island
Bradenton, FL
7% off
Price is £1,435
£1,435
£205 per night
includes taxes & fees
Image gallery for Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
1010 out of 10 rating
Exceptional
(39 reviews)
Beautifully Decorated Pool Home 2 Bed/2 Bath minutes away from Siesta Key Beach!
Sarasota, FL
8% off
Price is £2,555
£2,555
£365 per night
includes taxes & fees
Image gallery for Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
1010 out of 10 rating
Exceptional
(7 reviews)
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Siesta Key, FL
8% off
Price is £10,998
£10,998
£1,571 per night
includes taxes & fees
Image gallery for Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Your Beachside Retreat – Siesta Key’s White Sands Just Steps Away!
Siesta Key, FL
7% off
Price is £2,028
£2,028
£290 per night
includes taxes & fees
Image gallery for Tiki Tide Villa | Private POOL + Tiki Hut!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Tiki Tide Villa | Private POOL + Tiki Hut!
Sarasota, FL
7% off
Price is £2,848
£2,848
£407 per night
includes taxes & fees
Image gallery for Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
9.89.8 out of 10 rating
Exceptional
(119 reviews)
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
Siesta Key, FL
7% off
Price is £5,144
£5,144
£735 per night
includes taxes & fees
Image gallery for New home 3/2 renovation 3 miles to Siesta Key
9.29.2 out of 10 rating
Wonderful
(19 reviews)
New home 3/2 renovation 3 miles to Siesta Key
Sarasota, FL
7% off
Price is £995
£995
£142 per night
includes taxes & fees
Image gallery for Siesta Key FamilyGetaway!!
1010 out of 10 rating
Exceptional
(83 reviews)
Siesta Key FamilyGetaway!!
Siesta Key, FL
8% off
Price is £3,063
£3,063
£438 per night
includes taxes & fees
Image gallery for Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
1010 out of 10 rating
Exceptional
(12 reviews)
Welcome To Shoreline: 4BR, Heated Pool, 7miles to Gulf Beaches, Sleeps10
Sarasota, FL
7% off
Price is £2,496
£2,496
£357 per night
includes taxes & fees
Image gallery for Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Sandy Feet Retreat | Private Pool, Pergola + Ping Pong!
Sarasota, FL
7% off
Price is £2,135
£2,135
£305 per night
includes taxes & fees
Image gallery for Book now, and make memories that will last a lifetime in the heart of Sarasota!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Book now, and make memories that will last a lifetime in the heart of Sarasota!
Sarasota, FL
8% off
Price is £1,294
£1,294
£185 per night
includes taxes & fees
Image gallery for Charming Beach Cottage
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Charming Beach Cottage
Sarasota, FL
14% off
Price is £936
£936
£134 per night
includes taxes & fees
Image gallery for Siesta Key Beachside Condo-direct beach access
1010 out of 10 rating
Exceptional
(13 reviews)
Siesta Key Beachside Condo-direct beach access
Siesta Key, FL
8% off
Price is £2,102
£2,102
£300 per night
includes taxes & fees
Image gallery for Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
1010 out of 10 rating
Exceptional
(31 reviews)
Serene yard and pool, 1 mile to beach, pets OK, patio TV, Kayaks
Sarasota, FL
7% off
Price is £1,639
£1,639
£234 per night
includes taxes & fees
Image gallery for Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
1010 out of 10 rating
Exceptional
(17 reviews)
Bay Bliss Bungalow | 65" Smart TV, Lanai + Electric Bikes!
Sarasota, FL
6% off
Price is £1,512
£1,512
£216 per night
includes taxes & fees
Image gallery for Updated and upgraded. Close to Beaches, Downtown, Hospital.
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Updated and upgraded. Close to Beaches, Downtown, Hospital.
Sarasota, FL
11% off
Price is £1,874
£1,874
£268 per night
includes taxes & fees
Image gallery for Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key, FL
7% off
Price is £1,995
£1,995
£285 per night
includes taxes & fees
Image gallery for Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
1010 out of 10 rating
Exceptional
(12 reviews)
Sunshine Haven | HUGE Backyard, Private heated Pool + Fire Pit!
Sarasota, FL
6% off
Price is £1,577
£1,577
£225 per night
includes taxes & fees
Image gallery for Midcentury Modern 3 BR - With Pool in Sarasota, Close to Beaches!
9.89.8 out of 10 rating
Exceptional
(119 reviews)
Midcentury Modern 3 BR - With Pool in Sarasota, Close to Beaches!
Sarasota, FL
16% off
Price is £1,634
£1,634
£233 per night
includes taxes & fees
Image gallery for Luxury condo steps away from Siesta Key public beach
9.69.6 out of 10 rating
Exceptional
(69 reviews)
Luxury condo steps away from Siesta Key public beach
Siesta Key, FL
7% off
Price is £1,634
£1,634
£233 per night
includes taxes & fees
Image gallery for Newly Updated Jamaica Royale Villa: Private Beach, Pools, & Free Daily Activities!
9.69.6 out of 10 rating
Exceptional
(79 reviews)
Newly Updated Jamaica Royale Villa: Private Beach, Pools, & Free Daily Activities!
Siesta Key, FL
7% off
Price is £2,861
£2,861
£409 per night
includes taxes & fees
Image gallery for Bright & Beachy - Steps to the water! Community pool closure Aug 4-31st
1010 out of 10 rating
Exceptional
(89 reviews)
Bright & Beachy - Steps to the water! Community pool closure Aug 4-31st
Siesta Key, FL
8% off
Price is £2,126
£2,126
£304 per night
includes taxes & fees
Image gallery for Luxury Family size house, 9 miles away from siesta key, with pool
1010 out of 10 rating
Exceptional
(12 reviews)
Luxury Family size house, 9 miles away from siesta key, with pool
Sarasota, FL
18% off
Price is £1,735
£1,735
£248 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Bay Island
Siesta Key Pool Palace - Walk to Beach
Sleeps 12 · 5 bedrooms · 6 bathrooms
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach
Sleeps 8 · 4 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
56 reviews(56 reviews)
AMAZING 4 level SIESTA KEY home on large water with dock, crows nest, spa/pool
Sleeps 10 · 5 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
The Seagrape Villa - Luxury Accommodation in Paradise
Sleeps 10 · 5 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Siesta Key Sports Paradise- bball, vball, tennis, pickleball
Sleeps 6 · 2 bedrooms · 2+ bathrooms
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Sleeps 14 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Top rated rentals - Bay Island
Simply Fantastic!
1010 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Very very nice villa
1010 out of 10
Exceptionalexceptional
116 reviews(116 reviews)
Very well appointed property in an excellent location.
1010 out of 10
Exceptionalexceptional
114 reviews(114 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value