Bay Island holiday rentals

We found 7,093 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:22 Jan - 29 Jan

Pool
Exceptional
(28 reviews)

Rare private beachfront estate on the Gulf.

Nokomis

8% off
AU$38,653
for 7 nights, 1 home
AU$5,522 per night
includes taxes & fees
Rare private beachfront estate on the Gulf.
Pool
Exceptional
(12 reviews)

The Golden Palms

Sarasota

21% off
AU$15,001
for 7 nights, 1 home
AU$2,143 per night
includes taxes & fees
The Golden Palms
Picture #1
Exceptional
(83 reviews)

Jamaica Royale | 3 Pools, Beach & Free Activities

Siesta Key

7% off
AU$4,631
for 7 nights, 1 apartment
AU$662 per night
includes taxes & fees
Jamaica Royale | 3 Pools, Beach & Free Activities
Luxury Estate By The Bay - Close to Beach image 25
Exceptional
(18 reviews)

Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach

Sarasota

8% off
AU$14,992
for 7 nights, 1 home
AU$2,142 per night
includes taxes & fees
Sarasota Bayfront Estate - Sunset Views, Near Crescent Beach & Siesta Key Beach
Dining table right off the kitchen.
Exceptional
(148 reviews)

Lulu’s Loggerhead, Heated Pool, Walk to Village

Siesta Key

7% off
AU$4,912
for 7 nights, 1 apartment
AU$702 per night
includes taxes & fees
Lulu’s Loggerhead, Heated Pool, Walk to Village
Dining
Exceptional
(57 reviews)

Sarasota Waterfront Paradise- Location, Location...!!

Sarasota

8% off
AU$4,756
for 7 nights, 1 home
AU$679 per night
includes taxes & fees
Sarasota Waterfront Paradise- Location, Location...!!
Interior
Exceptional
(45 reviews)

KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE

Sarasota

7% off
AU$4,459
for 7 nights, 1 home
AU$637 per night
includes taxes & fees
KEY DREAMS-LARGE HEATED POOL-3 BR-10 MIN TO SIESTA KEY-SLEEPS 8-GULF GATE
Enjoy your morning coffee and cereal in the backyard with singing Seaside Sparrows....
Exceptional
(47 reviews)

Perfect Location, Dog Friendly, Mins to Siesta Key

Sarasota

7% off
AU$3,874
for 7 nights, 1 home
AU$553 per night
includes taxes & fees
Perfect Location, Dog Friendly, Mins to Siesta Key
BACKYARD OASIS WITH PRIVATE POOL
Exceptional
(52 reviews)

Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach

Siesta Key

8% off
AU$14,429
for 7 nights, 1 home
AU$2,061 per night
includes taxes & fees
Siesta Coastal Oasis - 5 Min Paved Walk to the Private Beach
Sophisticated and serene Mediterranean beach home.
Exceptional
(14 reviews)

Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock

Siesta Key

7% off
AU$10,964
for 7 nights, 1 home
AU$1,566 per night
includes taxes & fees
Casa del Siesta— Mediterranean Luxury by the Beach with Pool, Spa & Private Dock
Private kitchen
Excellent
(8 reviews)

3 Miles to Siesta Beach 3bdr/2bth with heated pool

Sarasota

7% off
AU$4,658
for 7 nights, 1 home
AU$665 per night
includes taxes & fees
3 Miles to Siesta Beach 3bdr/2bth with heated pool
additional bar area seating
Exceptional
(129 reviews)

HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes

Sarasota

5% off
AU$4,388
for 7 nights, 1 home
AU$627 per night
includes taxes & fees
HEATED pool, bike to Siesta, quiet street, 1 MILE to SK beach, kayaks & bikes
Resort Styled 5-bdrm waterfront w/Pool/Spa/FirePit/Putting Grn/Boat/Jet Ski Lift
Wonderful
(17 reviews)

Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit

Bradenton

8% off
AU$9,536
for 7 nights, 1 home
AU$1,362 per night
includes taxes & fees
Waterfront 5BR Luxury Home – Pool, Spa, Boat Lift, Putting Green, Fire Pit
Kitchen with a giant island and seating for four. Cooking essentials are stocked
Exceptional
(41 reviews)

A Whale of a Good Time!

Sarasota

8% off
AU$5,112
for 7 nights, 1 home
AU$730 per night
includes taxes & fees
A Whale of a Good Time!
Living area
Exceptional
(134 reviews)

Lido Beach Walk! One block to beach!

Sarasota

8% off
AU$2,271
for 7 nights, 1 room
AU$324 per night
includes taxes & fees
Lido Beach Walk! One block to beach!
Catch dinner at the fishing pier!
Wonderful
(46 reviews)

Poolside Style, Beachside Soul at SK's Bay Oaks!

Siesta Key

6% off
AU$2,844
for 7 nights, 1 apartment
AU$406 per night
includes taxes & fees
Poolside Style, Beachside Soul at SK's Bay Oaks!
Exterior
Exceptional
(44 reviews)

Siesta Key Beachside Condo-direct beach access

Siesta Key

8% off
AU$3,889
for 7 nights, 1 apartment
AU$556 per night
includes taxes & fees
Siesta Key Beachside Condo-direct beach access
Enjoy evenings on Siesta with a dip in the heated pool
Exceptional
(62 reviews)

Walk to Beach + Village, Beach Gear Included, Pool

Siesta Key

7% off
AU$4,549
for 7 nights, 1 apartment
AU$650 per night
includes taxes & fees
Walk to Beach + Village, Beach Gear Included, Pool
Picture #1
Wonderful
(65 reviews)

2-Story Townhome: Steps from the Sand & Gulf Views

Siesta Key

7% off
AU$5,527
for 7 nights, 1 apartment
AU$790 per night
includes taxes & fees
2-Story Townhome: Steps from the Sand & Gulf Views
Enjoy morning coffee or evening sunsets on the shared bayfront patio—complete with stunning water views.
Exceptional
(19 reviews)

Siesta Key Base | Walk to Beach | Free Activities

Siesta Key

6% off
AU$3,032
for 7 nights, 1 apartment
AU$433 per night
includes taxes & fees
Siesta Key Base | Walk to Beach | Free Activities
Private kitchen
Exceptional
(35 reviews)

Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!

Sarasota

8% off
AU$3,046
for 7 nights, 1 home
AU$435 per night
includes taxes & fees
Renovated 2-bed 2 bath home with Pool, Garage, just a bike ride to Siesta Key!
Pool
Excellent
(156 reviews)

Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL

Sarasota

8% off
AU$1,190
for 7 nights, 1 room
AU$170 per night
includes taxes & fees
Right on the Waterfront Marina - Suite 117 - 7150 N Tamiami Tail, Sarasota FL
Beach
Exceptional
(46 reviews)

Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

Sarasota

7% off
AU$2,622
for 7 nights, 1 home
AU$375 per night
includes taxes & fees
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Property grounds
Exceptional
(13 reviews)

Canalfront Siesta key entire King suite

Siesta Key

8% off
AU$2,603
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
Canalfront Siesta key entire King suite
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More 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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