Bay Island holiday rentals
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
AU$2,370
for 7 nights, 1 cottage
AU$339 per night
includes taxes & fees

Very good
(8 reviews)
Sarasota Modern Home minutes to Siesta & Downtown
Sarasota
AU$3,222
for 7 nights, 1 home
AU$460 per night
includes taxes & fees

Exceptional
(102 reviews)
Sarasota Cozy & Clean, Near #1 Beach Siesta in SouthGate Neighborhood
Sarasota
AU$1,284
for 7 nights, 1 apartment
AU$183 per night
includes taxes & fees

Exceptional
(242 reviews)
Great Value!!! Immaculate, minutes from the beach, With heated pool !!
Sarasota
AU$2,572
for 7 nights, 1 home
AU$367 per night
includes taxes & fees

Exceptional
(25 reviews)
Adorable Lido Beach Home- walk to beach and St. Armand's
Sarasota
AU$4,646
for 7 nights, 1 home
AU$664 per night
includes taxes & fees

Exceptional
(63 reviews)
Private Sarasota Pool Retreat Near Siesta Key Beach!
Sarasota
AU$2,639
for 7 nights, 1 home
AU$377 per night
includes taxes & fees

Exceptional
(103 reviews)
Stunning 2BR/2BA Home with Private Heated Pool, Minutes from Siesta Key
Sarasota
AU$2,360
for 7 nights, 1 home
AU$337 per night
includes taxes & fees

Exceptional
(46 reviews)
🌴 Peaceful Sarasota Home with Patio, 2BR, 2BA Near Lido Beach & Downtown
Sarasota
AU$1,647
for 7 nights, 1 home
AU$235 per night
includes taxes & fees

Exceptional
(72 reviews)
Relaxing Lakefront Home: 3BR/2BA, Heated Pool, Near Siesta Key Beach
Sarasota
AU$2,989
for 7 nights, 1 home
AU$427 per night
includes taxes & fees

Exceptional
(11 reviews)
Siesta Vista, Spacious Waterfront Home. One Block to Beach & Village. Roof Deck!
Siesta Key
AU$12,494
for 7 nights, 1 home
AU$1,785 per night
includes taxes & fees

Exceptional
(20 reviews)
Charming 2-bedroom house in the heart of Sarasota—A quaint nature escape
Sarasota
AU$1,734
for 7 nights, 1 home
AU$248 per night
includes taxes & fees

Exceptional
(23 reviews)
Good Vibrations- Stay right ON the beach in Siesta Key! Sleeps 6
Siesta Key
AU$4,163
for 7 nights, 1 apartment
AU$595 per night
includes taxes & fees

Excellent
(156 reviews)
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Sarasota
AU$1,156
for 7 nights, 1 room
AU$165 per night
includes taxes & fees

Very good
(164 reviews)
SARASOTA Waterfront hotel Room KING BED # 215 ON SARA BAY 7150 N Tamiami Trail
Sarasota
AU$942
for 7 nights, 1 room
AU$135 per night
includes taxes & fees

Exceptional
(22 reviews)
Southside Bungalow - Sleeps 8 - Pool, Spa & Putting Green
Sarasota
AU$7,150
for 7 nights, 1 home
AU$1,021 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
AU$3,647
for 7 nights, 1 apartment
AU$521 per night
includes taxes & fees

Exceptional
(129 reviews)
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Sarasota
AU$4,713
for 7 nights, 1 home
AU$673 per night
includes taxes & fees

Exceptional
(107 reviews)
Palm Bay Club - Bayfront Large 2/2 Condo - Reasonable Price
Siesta Key
AU$3,420
for 7 nights, 1 apartment
AU$489 per night
includes taxes & fees

Exceptional
(85 reviews)
Private Villa Beachside complex, Siesta Key private beach access 2br/2ba patio
Siesta Key
AU$3,572
for 7 nights, 1 villa
AU$510 per night
includes taxes & fees

Wonderful
(16 reviews)
Luxury Waterfront Views / Pool / 1400sf / Minutes to Beach
Siesta Key
AU$4,032
for 7 nights, 1 apartment
AU$576 per night
includes taxes & fees

Excellent
(160 reviews)
Sarasota “Executive Waterfront Suite” A hotel rm # 103 on Sara Bay Marina
Sarasota
AU$1,156
for 7 nights, 1 room
AU$165 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
AU$2,646
for 7 nights, 1 home
AU$378 per night
includes taxes & fees

Exceptional
(38 reviews)
Siesta Key Beachside Condo-direct beach access
Siesta Key
AU$3,776
for 7 nights, 1 apartment
AU$539 per night
includes taxes & fees

Exceptional
(52 reviews)
Get here fast, then take it slow... Right — ON — Siesta Beach at Condo Kokomo!
Siesta Key
AU$2,964
for 7 nights, 1 apartment
AU$423 per night
includes taxes & fees
Find spaces that suit your style
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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
When is the best time to visit Bay Island for a holiday rental?
January is the most popular time to visit Bay Island, Florida, as the peak season runs from January to March. During these months, travellers flock to the area to enjoy the warm, sunny climate, with temperatures typically ranging from 15 to 25 degrees Celsius. This is an ideal time for outdoor activities, such as beach lounging, water sports, and exploring the local attractions.With plenty of sunshine and comfortable weather, January offers a great backdrop for sightseeing and relaxation. Visitors can partake in various activities, from strolling along the pristine beaches to indulging in local cuisine at waterfront restaurants. The vibrant setting during this time creates an enjoyable experience for those seeking adventure and leisure alike.For those looking to save a bit on holiday rentals, November presents a lovely opportunity. While it's considered the low season, the weather remains pleasant, and the area is quieter, allowing for a more peaceful getaway. This month is great for leisurely walks along the beach or discovering hidden gems without the crowds.Ultimately, your choice of when to visit Bay Island will depend on whether you prefer the lively buzz of peak season or the tranquil charm of the quieter months.
What are the top attractions in Bay Island, Florida, United States of America?
In Bay Island, Florida, visitors can enjoy a variety of attractions that highlight the natural beauty and recreational opportunities of the area. The nearby Gulf Beaches offer pristine sandy shores and warm waters ideal for sunbathing and water sports. The island is also close to the scenic Pinellas Trail, superb for cycling and walking enthusiasts, providing picturesque views of the surrounding landscape.For those interested in wildlife, the nearby Fort De Soto Park features beautiful beaches, nature trails, and opportunities for birdwatching and kayaking. The vibrant local community often hosts events and markets, adding to the charm of the area.
Are all fees included in the Bay Island holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Bay Island holiday homes with parking?
Stayz offers a wide selection of holiday homes in Bay Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Bay Island holiday homes?
You can find great discounts on holiday homes in Bay Island on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Bay Island holiday home booking on Stayz?
To find Bay Island holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Bay Island?
A long-stay holiday home in Bay Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Bay Island holiday home?
Book your Bay Island holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Bay Island?
Prices for holiday homes in Bay Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Bay Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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