Bay Island holiday homes
We found 6,339 holiday rentals — enter your dates for availability
Discover a selection of 7 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:24 Oct - 31 Oct
Image gallery for Siesta Key Luxury Bayfront Home Steps from the World's Finest Beaches
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Siesta Key Luxury Bayfront Home Steps from the World's Finest Beaches
Siesta Key, FL
8% off
Price is NZ$13,398
NZ$13,398
NZ$1,914 per night
includes taxes & fees
Image gallery for Flip off your Flops at the Faded Oasis!
1010 out of 10 rating
Exceptional
(5 reviews)
Flip off your Flops at the Faded Oasis!
Sarasota, FL
7% off
Price is NZ$4,908
NZ$4,908
NZ$701 per night
includes taxes & fees
Image gallery for Junior Suite - Large, 2 king beds, 1 private bath in great and historic location
9.49.4 out of 10 rating
Exceptional
(20 reviews)
Junior Suite - Large, 2 king beds, 1 private bath in great and historic location
Sarasota, FL
12% off
Price is NZ$1,978
NZ$1,978
NZ$283 per night
includes taxes & fees
Image gallery for The Bray Escape. 4.7 Miles to Siesta Key
1010 out of 10 rating
Exceptional
(11 reviews)
The Bray Escape. 4.7 Miles to Siesta Key
Sarasota, FL
7% off
Price is NZ$3,287
NZ$3,287
NZ$470 per night
includes taxes & fees
Image gallery for TROPICAL 2 BEDROOM "TREE HOUSE" UNIT "B" ON EQUINE RANCH
1010 out of 10 rating
Exceptional
(14 reviews)
TROPICAL 2 BEDROOM "TREE HOUSE" UNIT "B" ON EQUINE RANCH
Sarasota, FL
7% off
Price is NZ$2,339
NZ$2,339
NZ$334 per night
includes taxes & fees
Image gallery for Charming Sunny House 5 min by Siesta Key Beach 5 min Downtown Sarasota
8.48.4 out of 10 rating
Very good
(7 reviews)
Charming Sunny House 5 min by Siesta Key Beach 5 min Downtown Sarasota
Sarasota, FL
8% off
Price is NZ$4,137
NZ$4,137
NZ$591 per night
includes taxes & fees
Image gallery for Coastal modern POOL home
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Coastal modern POOL home
Sarasota, FL
7% off
Price is NZ$2,834
NZ$2,834
NZ$405 per night
includes taxes & fees
Image gallery for Lovely one bedroom condo near Siesta Key Beach
9.09.0 out of 10 rating
Wonderful
(26 reviews)
Lovely one bedroom condo near Siesta Key Beach
Sarasota, FL
7% off
Price is NZ$1,739
NZ$1,739
NZ$248 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
(88 reviews)
Bright & Beachy - Steps to the water! Community pool closure Aug 4-31st
Siesta Key, FL
8% off
Price is NZ$4,134
NZ$4,134
NZ$591 per night
includes taxes & fees
Image gallery for Charming Beach Cottage
9.69.6 out of 10 rating
Exceptional
(26 reviews)
Charming Beach Cottage
Sarasota, FL
14% off
Price is NZ$2,015
NZ$2,015
NZ$288 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
(18 reviews)
New home 3/2 renovation 3 miles to Siesta Key
Sarasota, FL
7% off
Price is NZ$2,124
NZ$2,124
NZ$303 per night
includes taxes & fees
Image gallery for 5 minutes to private Siesta Key Beach + 2 heated pools and pickleball courts
1010 out of 10 rating
Exceptional
(10 reviews)
5 minutes to private Siesta Key Beach + 2 heated pools and pickleball courts
Siesta Key, FL
8% off
Price is NZ$4,921
NZ$4,921
NZ$703 per night
includes taxes & fees
Image gallery for Peaceful And Private Unit, With Cover Parking
9.69.6 out of 10 rating
Exceptional
(16 reviews)
Peaceful And Private Unit, With Cover Parking
Sarasota, FL
7% off
Price is NZ$1,463
NZ$1,463
NZ$209 per night
includes taxes & fees
Image gallery for 3 Bedroom House North End of Siesta Key - Short Walk To Shell Beach
9.89.8 out of 10 rating
Exceptional
(12 reviews)
3 Bedroom House North End of Siesta Key - Short Walk To Shell Beach
Siesta Key, FL
8% off
Price is NZ$5,616
NZ$5,616
NZ$802 per night
includes taxes & fees
Image gallery for PEACEFUL AND SPACIOUS POND VIEW HOME ON EQUINE RANCH
8.48.4 out of 10 rating
Very good
(5 reviews)
PEACEFUL AND SPACIOUS POND VIEW HOME ON EQUINE RANCH
Sarasota, FL
7% off
Price is NZ$2,886
NZ$2,886
NZ$412 per night
includes taxes & fees
Image gallery for Tropical oasis minutes to Siesta Beach
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Tropical oasis minutes to Siesta Beach
Sarasota, FL
8% off
Price is NZ$2,700
NZ$2,700
NZ$386 per night
includes taxes & fees
Image gallery for Siesta Key Private Lakefront Oasis. Beautiful 3 Bdrm Home with Heated Pool.
1010 out of 10 rating
Exceptional
(26 reviews)
Siesta Key Private Lakefront Oasis. Beautiful 3 Bdrm Home with Heated Pool.
Siesta Key, FL
8% off
Price is NZ$6,780
NZ$6,780
NZ$969 per night
includes taxes & fees
Image gallery for Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Siesta Key, FL
17% off
Price is NZ$4,775
NZ$4,775
NZ$682 per night
includes taxes & fees
Image gallery for Great location !Private 2 bed -1 bath pool home . Just minutes to Siesta key.
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Great location !Private 2 bed -1 bath pool home . Just minutes to Siesta key.
Sarasota, FL
8% off
Price is NZ$3,786
NZ$3,786
NZ$541 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 NZ$3,241
NZ$3,241
NZ$463 per night
includes taxes & fees
Image gallery for Siesta Key Beach HideAway
9.29.2 out of 10 rating
Wonderful
(53 reviews)
Siesta Key Beach HideAway
Siesta Key, FL
8% off
Price is NZ$6,153
NZ$6,153
NZ$879 per night
includes taxes & fees
Image gallery for A+ location #1 Beach Siesta Key w heated pool, arcade, & small dog friendly
8.68.6 out of 10 rating
Excellent
(7 reviews)
A+ location #1 Beach Siesta Key w heated pool, arcade, & small dog friendly
Siesta Key, FL
7% off
Price is NZ$2,990
NZ$2,990
NZ$427 per night
includes taxes & fees
Image gallery for King Bed • Private Home • Walk to Beach & Village • Heated Pool & Spa • No Steps
1010 out of 10 rating
Exceptional
(56 reviews)
King Bed • Private Home • Walk to Beach & Village • Heated Pool & Spa • No Steps
Siesta Key, FL
8% off
Price is NZ$5,814
NZ$5,814
NZ$831 per night
includes taxes & fees
Image gallery for Old Florida bungalow in Sarasota‘s best location
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Old Florida bungalow in Sarasota‘s best location
Sarasota, FL
7% off
Price is NZ$2,753
NZ$2,753
NZ$393 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
Private Indoor/Outdoor POOL & Waterfront Oasis on Siesta Key
Sleeps 14 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
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)
Stunning Siesta Key,, . , Walk to Shell Beach, HEATED POOL - Discounts
Sleeps 14 · 5 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
118 reviews(118 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, 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.