Bay Island holiday homes
We found 6,852 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:27 Nov - 4 Dec
Exceptional
(30 reviews)
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks, large backyard
Sarasota
NZ$2,792
for 7 nights, 1 cottage
NZ$399 per night
includes taxes & fees
Very good
(8 reviews)
Sarasota Modern Home minutes to Siesta & Downtown
Sarasota
NZ$3,874
for 7 nights, 1 home
NZ$553 per night
includes taxes & fees
Exceptional
(102 reviews)
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Sarasota
NZ$1,545
for 7 nights, 1 apartment
NZ$221 per night
includes taxes & fees
Exceptional
(242 reviews)
Great Value!!! Immaculate, minutes from the beach, With heated pool !!
Sarasota
NZ$3,069
for 7 nights, 1 home
NZ$438 per night
includes taxes & fees
Exceptional
(25 reviews)
Adorable Lido Beach Home- walk to beach and St. Armand's
Sarasota
NZ$5,686
for 7 nights, 1 home
NZ$812 per night
includes taxes & fees
Exceptional
(63 reviews)
Private Sarasota Pool Retreat Near Siesta Key Beach!
Sarasota
NZ$3,149
for 7 nights, 1 home
NZ$450 per night
includes taxes & fees
Exceptional
(46 reviews)
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Sarasota
NZ$1,983
for 7 nights, 1 home
NZ$283 per night
includes taxes & fees
Exceptional
(103 reviews)
Stunning 2BR/2BA Home with Private Heated Pool, Minutes from Siesta Key
Sarasota
NZ$2,780
for 7 nights, 1 home
NZ$397 per night
includes taxes & fees
Exceptional
(72 reviews)
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Sarasota
NZ$3,596
for 7 nights, 1 home
NZ$514 per night
includes taxes & fees
Exceptional
(11 reviews)
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Siesta Key
NZ$14,934
for 7 nights, 1 home
NZ$2,133 per night
includes taxes & fees
Exceptional
(20 reviews)
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Sarasota
NZ$2,087
for 7 nights, 1 home
NZ$298 per night
includes taxes & fees
Exceptional
(23 reviews)
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Siesta Key
NZ$5,094
for 7 nights, 1 apartment
NZ$728 per night
includes taxes & fees
Excellent
(156 reviews)
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Sarasota
NZ$1,406
for 7 nights, 1 room
NZ$201 per night
includes taxes & fees
Very good
(164 reviews)
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Sarasota
NZ$1,147
for 7 nights, 1 room
NZ$164 per night
includes taxes & fees
Exceptional
(22 reviews)
Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green
Sarasota
NZ$7,786
for 7 nights, 1 home
NZ$1,112 per night
includes taxes & fees
Wonderful
(161 reviews)
Palm Bay Club Bayside Well-Priced Condo on Siesta Key 2 bed and 2 bath unit
Siesta Key
NZ$4,464
for 7 nights, 1 apartment
NZ$638 per night
includes taxes & fees
Exceptional
(129 reviews)
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Sarasota
NZ$5,769
for 7 nights, 1 home
NZ$824 per night
includes taxes & fees
Exceptional
(107 reviews)
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Siesta Key
NZ$4,112
for 7 nights, 1 apartment
NZ$587 per night
includes taxes & fees
Exceptional
(85 reviews)
Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio
Siesta Key
NZ$4,371
for 7 nights, 1 villa
NZ$624 per night
includes taxes & fees
Wonderful
(16 reviews)
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Siesta Key
NZ$4,935
for 7 nights, 1 apartment
NZ$705 per night
includes taxes & fees
Excellent
(160 reviews)
Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina
Sarasota
NZ$1,406
for 7 nights, 1 room
NZ$201 per night
includes taxes & fees
Exceptional
(34 reviews)
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Sarasota
NZ$3,159
for 7 nights, 1 home
NZ$451 per night
includes taxes & fees
Exceptional
(38 reviews)
Siesta Key Beachside Condo-direct beach access
Siesta Key
NZ$4,621
for 7 nights, 1 apartment
NZ$660 per night
includes taxes & fees
Exceptional
(52 reviews)
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Siesta Key
NZ$3,548
for 7 nights, 1 apartment
NZ$507 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
Casa Flamingo – A Private Waterfront/Pool Resort Estate on Siesta Key
Sleeps 14 · 7 bedrooms · 6+ bathrooms
The Lookout - 891 “Siesta Key’
Sleeps 10 · 5 bedrooms · 6+ bathrooms
SERENITY SIESTA/OLD FLORIDA FEEL/SANDY BEACH/GULF IN THE BACKYARD
Sleeps 8 · 4 bedrooms · 3+ bathrooms
Escape to The Big Dipper: Siesta Key Canal Front Home with Pool and Private Dock
Sleeps 10 · 4 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 home 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. Bookabach 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 home in Bay Island?
The average price for a holiday home 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 Bookabach. 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 homes in Bay Island?
Happily, yes. You can choose from 10 holiday homes that roll out the welcome mat in Bay Island on Bookabach. Our furry best friends need a getaway too, so simply use our search function for pet-friendly holiday homes 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 Bookabach, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Bay Island?
When it comes to home amenities that guests look for in Bay Island, a water view, a fireplace and a garden rank highest. With Bookabach 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 homes 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 homes 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 homes with WiFi in Bay Island?
Bay Island has five holiday homes 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 Bookabach homes make it a cinch to get online.
How can I find holiday homes 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 home in Bay Island?
The minimum age is normally 16, 18 or 21. It can change between properties on Bookabach, so look at the rules of your preferred Bay Island holiday home before booking.
How long can I rent a holiday home 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 Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.
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- Aloha Kai Holiday Rentals
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- St. Armands Circle Holiday Rentals
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- Sunset Royale Holiday Rentals
- Lido Beach Holiday Rentals
- Crescent Beach Holiday Rentals
- Gulf & Bay Club Bayside Holiday Rentals
- Lido Beach Club Holiday Rentals
- Alta Vista Holiday Rentals
- Palm Bay Club Holiday Rentals
- Siesta Key Holiday Rentals
- House of the Sun Holiday Rentals
- Siesta Key Village Holiday Rentals
- Lido Shores Holiday Rentals
- Castel del Mare Holiday Rentals
- Our House at The Beach Holiday Rentals
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- Island House Holiday Rentals
- Saint Armands Key Holiday Rentals
- Shell Beach Holiday Rentals
- Lido Key Holiday Rentals
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