Bay Island holiday rentals
We found 6,809 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Bay Island that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as a fireplace and a washer and dryer. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts – Bay Island
Showing deals for:4 Dec - 11 Dec
Exceptional
(117 reviews)
Pineapple House - near beaches - private SOUTH facing POOL & HOT TUB - walkable
Sarasota
S$3,249
for 7 nights, 1 home
S$464 per night
includes taxes & fees
Exceptional
(288 reviews)
Immaculate, 3 bedroom, 2 bath Close to Siesta Beach, with secluded HEATED POOL
Sarasota
S$2,241
for 7 nights, 1 home
S$320 per night
includes taxes & fees
Exceptional
(84 reviews)
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Sarasota
S$2,400
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Exceptional
(7 reviews)
Tropical Heart Villa is walking distance to Downtown and a 5 min drive to Beach!
Sarasota
S$2,235
for 7 nights, 1 villa
S$319 per night
includes taxes & fees
Exceptional
(30 reviews)
Adorable 1 Bedroom, 1 Bath guesthouse < 1block to Lido Beach
Sarasota
S$2,737
for 7 nights, 1 room
S$391 per night
includes taxes & fees
Exceptional
(44 reviews)
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Sarasota
S$3,124
for 7 nights, 1 home
S$446 per night
includes taxes & fees
Exceptional
(73 reviews)
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Sarasota
S$2,763
for 7 nights, 1 home
S$395 per night
includes taxes & fees
Exceptional
(12 reviews)
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Siesta Key
S$10,472
for 7 nights, 1 home
S$1,496 per night
includes taxes & fees
Exceptional
(46 reviews)
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Sarasota
S$1,501
for 7 nights, 1 home
S$214 per night
includes taxes & fees
Exceptional
(189 reviews)
LAKEFRONT 2bed/2bath with Heated POOL house, JUST 5 min away SIESTA KEY BEACH!
Sarasota
S$2,044
for 7 nights, 1 home
S$292 per night
includes taxes & fees
Exceptional
(52 reviews)
NO Bunks-King beds, Garage Parking, Private Beach Access-Less Crowded
Siesta Key
S$8,897
for 7 nights, 1 home
S$1,271 per night
includes taxes & fees
Exceptional
(20 reviews)
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Sarasota
S$1,533
for 7 nights, 1 home
S$219 per night
includes taxes & fees
Exceptional
(24 reviews)
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 5 Minutes to Beaches
Sarasota
S$3,395
for 7 nights, 1 villa
S$485 per night
includes taxes & fees
Exceptional
(64 reviews)
Private Sarasota Pool Retreat Near Siesta Key Beach!
Sarasota
S$2,380
for 7 nights, 1 home
S$340 per night
includes taxes & fees
Exceptional
(42 reviews)
Downtown Sarasota, Casa de Zara
Sarasota
S$2,402
for 7 nights, 1 home
S$343 per night
includes taxes & fees
Exceptional
(22 reviews)
Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green
Sarasota
S$6,408
for 7 nights, 1 home
S$915 per night
includes taxes & fees
Wonderful
(15 reviews)
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Bradenton
S$7,482
for 7 nights, 1 home
S$1,069 per night
includes taxes & fees
Exceptional
(129 reviews)
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Sarasota
S$3,637
for 7 nights, 1 home
S$520 per night
includes taxes & fees
Exceptional
(85 reviews)
Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio
Siesta Key
S$3,356
for 7 nights, 1 villa
S$479 per night
includes taxes & fees
Wonderful
(16 reviews)
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Siesta Key
S$3,742
for 7 nights, 1 apartment
S$535 per night
includes taxes & fees
Exceptional
(16 reviews)
A Private Siesta Key Waterfront Estate with Extraordinary Indoor/Outdoor Pool
Siesta Key
S$18,054
for 7 nights, 1 home
S$2,579 per night
includes taxes & fees
Exceptional
(132 reviews)
BE ON THE B E A C H! 2B/2B GREAT LOCATION!
Siesta Key
S$2,550
for 7 nights, 1 apartment
S$364 per night
includes taxes & fees
Exceptional
(23 reviews)
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Siesta Key
S$3,175
for 7 nights, 1 apartment
S$454 per night
includes taxes & fees
Exceptional
(44 reviews)
Island House Resort - Waterfront 2-bedroom condo directly on Siesta Key Beach!
Siesta Key
S$3,575
for 7 nights, 1 room
S$511 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Bay Island
Another Day in Paradise!
Sleeps 5 · 2 bedrooms · 2 bathrooms
The Seagrape Villa -Family Friendly- Luxury Accommodation in Paradise
Sleeps 10 · 5 bedrooms · 3+ bathrooms
A Private Siesta Key Waterfront Estate with Extraordinary Indoor/Outdoor Pool
Sleeps 14 · 6 bedrooms · 6+ bathrooms
The Lookout - 891 “Siesta Key’
Sleeps 10 · 5 bedrooms · 6+ bathrooms
Siesta Key Oceanfront Palace with Private Beach
Sleeps 10 · 5 bedrooms · 7 bathrooms
Gorgeous Canalfront Home w/ Heated Pool • 5-Min Walk to Lido Beach • Boat Dock
Sleeps 6 · 3 bedrooms · 3 bathrooms
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, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental accommodation in Bay Island?
Based on our data, houses are the most in-demand property type in Bay Island. But of course, everyone's idea of an epic stay will differ. Vrbo has holiday homes in a variety of sizes and shapes, so you're sure to find your perfect match.
How much does it cost to rent a holiday rental in Bay Island?
The average price for a holiday rental in Bay Island depends on a number of factors, such as length of stay, property type and season. Whether you're thinking about a sprawling villa with a pool or a cosy cabin ideal for just you and the kids, just add your travel dates to discover stays with terrific value.
How much does it cost to rent a beach house in Bay Island?
When you travel and the style and size of the property will influence the cost of your beachside stay. Click on your Bay Island travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to pick the amenities and features you want.
Are there pet-friendly holiday rentals in Bay Island?
Happily, yes. You can choose from 10 holiday homes that roll out the welcome mat in Bay Island on Vrbo. Our furry best friends need a getaway too, so simply use our search function for pet-friendly holiday rentals to book a perfect pad where your doggie can lap up the good times.
Can I rent a house with a pool in Bay Island?
Pack your swimsuit and inflatable unicorn, because there are 10 houses with a private pool in Bay Island. Make a booking at one of these popular holiday homes and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Bay Island?
When it comes to rental amenities that guests look for in Bay Island, a water view, a fireplace and a garden rank highest. With Vrbo holiday homes, there are choices to fit your style and taste, whether you're going on a holiday with family, friends or even pets.
Are there large group holiday rentals in Bay Island?
Take your pick of three properties in Bay Island that can sleep 10 or more people. Whether you're planning a trip with extended family or a special event like a birthday party, there's plenty of room to get your loved ones together under one roof.
Are there holiday rentals in Bay Island that welcome kids?
Bay Island has 10 family-friendly holiday homes to pick from. And securing a stay that welcomes kiddos is simple with our "Properties good for families" filter. In addition to having the entire place to yourselves, you'll get amenities and perks such as bunk beds, kitchens and private pools.
What are the top attractions for families in Bay Island?
There are plenty of wonderful things to do and see with the family in Bay Island, including:
- Siesta Key Beach
- Crescent Beach
- Shell Beach
Are there holiday rentals with WiFi in Bay Island?
Bay Island has five holiday rentals with WiFi, so you can stay connected while you're travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movie blockbusters to checking emails, these Vrbo homes make it a cinch to get online.
How can I find holiday rentals with air conditioning in Bay Island?
There are 10 holiday homes with air conditioning in Bay Island offering that gentle, cool breeze and extra element of comfort. Enter your chosen travel dates and then make use of our filters to look for properties with air conditioning.
How old do you have to be to rent a holiday rental in Bay Island?
The minimum age is normally 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Bay Island holiday home before booking.
How long can I rent a holiday rental in Bay Island for?
The amount of time you can rent a Bay Island holiday home for is down to each property. Just tap in your travel dates to browse available options that offer extended stays. They feature all you need to make your extended holiday more convenient and comfortable, such as laundries and air conditioning. Some Vrbo holiday rentals may also offer weekly or monthly discounted prices, so you can hang around longer for less.