Bay Island vacation rentals

We found 6,662 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Bay Island that are perfect for your trip. Vacation homes offer the amenities you expect for you and your friends, family, or even pets, such as WiFi and a pool. At the end of the day, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Bay Island

Showing deals for:May 22 - May 29

Image gallery for Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

Backyard on a clear sunny day, full fenced with privacy
9.8 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

Sarasota

7% off
Price is $124
$869 for 7 nights
All fees included
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Bay Island

Why visit Bay Island

  • Stunning Beaches: Bay Island boasts beautiful beaches perfect for sunbathing, swimming, and beachcombing.
  • Outdoor Activities: Enjoy a variety of outdoor adventures, from water sports to scenic walks in urban parks.
  • Family-Friendly Atmosphere: The tranquil environment makes Bay Island ideal for families looking to relax and bond.
  • Charming Neighborhood: Explore picturesque homes and a friendly community that embodies coastal living.
  • Great Accommodations: Choose from private homes, condos, and apartments with fantastic amenities for a comfortable stay.

Popular types of accommodation around Bay Island

Planning a getaway to Bay Island? You’re in for a treat. Discover the most sought-after accommodations, including houses, condos, and apartments. Enjoy fantastic amenities like fitness centers, private balconies, and convenient parking spaces. Plus, don’t miss out on the outdoor amenities that make your stay even more enjoyable. Dive into your Bay Island adventure with the perfect place to unwind.

  • Houses: The top choice for visitors to Bay Island, offering spacious accommodations ideal for families or groups seeking comfort and privacy.
  • Condos: A favored option for travelers, these modern units provide amenities and stunning views, perfect for a relaxing getaway.
  • Apartments: A great selection for those looking for a home-like feel, offering convenience and accessibility to local attractions.
  • Villas: These luxurious retreats boast elegant designs and private pools, ideal for a lavish escape.
  • Cottages: A charming and cozy option, perfect for couples or solo travelers wanting a quaint experience.**

Top attractions near Bay Island

Bay Island in Siesta Key, Florida, is an ideal destination for beach lovers and families seeking outdoor adventures. Visitors can explore beautiful beaches, urban parks, and marinas, making it a perfect spot for those wanting to enjoy both natural beauty and city experiences. Whether you're traveling with family or friends, Bay Island offers a variety of attractions to ensure a memorable vacation.

  • Siesta Key Beach: Renowned for its powdery white sand and stunning sunsets, Siesta Key Beach offers a relaxed atmosphere perfect for sunbathing, swimming, and beach volleyball. Its crystal-clear waters make it a favorite spot for families and beach lovers alike.
  • St. Armands Circle: A vibrant shopping and dining district, St. Armands Circle features unique boutiques, art galleries, and a variety of restaurants. The lively ambiance and beautiful landscaping create a perfect setting for a stroll or an outdoor meal.
  • Marina Jack: This bustling marina offers boat rentals, dining, and waterfront activities. With its stunning views of Sarasota Bay, Marina Jack is ideal for adventure seekers looking to explore the water, enjoy fresh seafood, or relax by the shore.

Things to do recommended for couples

For a romantic getaway in Bay Island, enjoy a captivating concert at the Beatrice Friedman Symphony Center, just 3 miles away. Alternatively, embrace some friendly competition at Evie's Golf Center, a mini-golf spot 5 miles away, perfect for adventurous couples looking to bond over fun.

Things to do recommended for families

Your family will have a fantastic time at Ed Smith Stadium, just 4 miles from Bay Island, where you can soak in the sports atmosphere. For relaxation, visit Nathan Benderson Park, 8 miles away, or the Robert L. Taylor Community Complex, 5 miles away, both perfect for wellness activities.

Things to do recommended for groups

Experience the vibrant arts at the Van Wezel Performing Arts Hall, just 3 miles from Bay Island. For adventure, hike the scenic Sarasota BayWalk, also 3 miles away. If sports are your thing, enjoy a round at the Gulf Gate Golf Club, located 4 miles from your stay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Bay Island

When traveling with a group, family, or pets, or if you're seeking longer stays, it's important to prioritize your preferences. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Bay Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for these options and much more on Vrbo.
  • Traveling to Bay Island with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Bay Island: For many families, a getaway wouldn’t be the same without their furry companion. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bay Island: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Bay Island

Experience the charm of Bay Island, a tranquil waterfront neighborhood in Siesta Key, Florida. Perfect for family-friendly vacations, this tropical haven offers stunning scenery and a relaxing atmosphere. Explore nearby attractions, indulge in island living, and discover beautiful homes that reflect the coastal lifestyle. Whether you're lounging on the beach or enjoying outdoor activities, Bay Island is the ideal destination for a memorable getaway.

  • Siesta Key: Siesta Key is a picturesque island city known for its stunning white-sand beaches and vibrant family-friendly atmosphere. Nestled in the Gulf of Mexico, it's an ideal destination for those seeking outdoor adventures and relaxation. Visitors can enjoy a variety of recreational areas, shopping malls, and luxurious resorts. The local attractions include the renowned Siesta Beach, which consistently ranks among the best beaches in the United States, and charming neighborhood spots perfect for family outings. Whether you’re sunbathing, swimming, or exploring the local dining scene, Siesta Key offers an unforgettable beach experience.
  • Sarasota: Located a short 3 miles from Bay Island, Sarasota is a lively city that combines beach charm with urban sophistication. Known for its cultural attractions and family-friendly activities, Sarasota is home to numerous shopping centers and resorts, providing plenty of entertainment options. Explore the beautiful beaches, including Lido Beach and Siesta Key Beach, both just a stone's throw away. Visitors can also immerse themselves in the local arts scene, with theaters, galleries, and museums adding to the city’s appeal. Sarasota is perfect for those wanting to experience a dynamic city atmosphere while enjoying the coastal lifestyle.
  • Lido Key: Just 2 miles from Bay Island, Lido Key is a serene island retreat known for its beautiful beaches and lush urban parks. This destination attracts families and beach lovers alike, offering a mix of relaxation and outdoor activities. Visitors can explore the local shopping centers and recreational areas, making it easy to find the perfect spot to unwind. The island's stunning beaches provide a perfect backdrop for sunbathing and water sports, while the nearby parks offer a peaceful escape for nature enthusiasts. Lido Key is an ideal spot for those looking to enjoy a tranquil island experience without straying too far from the city.

Best time to go to Bay Island

If you're planning a trip to Bay Island, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs in February to March and July, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January62.6°F (17.0°C)Light RainMostly SunnyAverageSlightly Low
February65.1°F (18.4°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March68.0°F (20.0°C)No Rain (Dry)SunnyModerately HighSlightly High
April73.4°F (23.0°C)Light RainMostly SunnyAverageSlightly High
May77.7°F (25.4°C)Light RainMostly SunnyAverageAverage
June81.7°F (27.6°C)Light RainMostly SunnyAverageAverage
July82.9°F (28.3°C)Light RainMostly SunnyModerately HighSlightly High
August83.3°F (28.5°C)Light RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Light RainMostly SunnyModerately LowSlightly Low
October77.2°F (25.1°C)Light RainMostly SunnyModerately LowSlightly Low
November70.7°F (21.5°C)No Rain (Dry)Mostly SunnyModerately LowAverage
December66.6°F (19.2°C)No Rain (Dry)Mostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your upcoming trip? Consider being flexible with your travel dates, as prices can change significantly. Also, extending your stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you'll receive OneKeyCash for the total booking amount. It truly benefits you to be the planner. Become a member of our One Key rewards program to unlock special savings and accumulate OneKeyCash on eligible stays. Sign up now and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your journeys, pick up right where you left off, and manage your travel arrangements. You can easily access the properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Bay Island?
In Bay Island, vacation houses and villas are the most popular types of rental accommodations, with several options available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or decks, superb for enjoying the warm Florida weather. Many rentals are located near the beach or waterfront, allowing guests to easily access local attractions and enjoy activities like fishing or boating.
Are there any beach house rentals in Bay Island?
In Bay Island, there are around 20 beach house rentals available, showcasing a variety of options for travelers. These properties are typically located in serene neighborhoods close to the water, providing easy access to the beach and stunning views. Most beach houses come equipped with amenities such as fully stocked kitchens, spacious living areas, and outdoor patios or decks—ideal for enjoying sunsets and gatherings with friends and family.
How much does it cost to rent a vacation home in Bay Island?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Bay Island to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Bay Island vacation house rentals?
You can find great discounts on house rentals in Bay Island on Vrbo, 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.
What are popular rental amenities in Bay Island?
In Bay Island, popular rental amenities cater to a comfortable and convenient stay. Travelers can expect vacation rentals equipped with fully functional kitchens, allowing guests to prepare their own meals. Many properties feature private pools, providing a refreshing oasis for relaxation and leisure. Additional amenities often include coffee and tea makers for a cozy start to the day, onsite parking for easy access, and blenders for whipping up smoothies or cocktails.
Can I find family house rentals in Bay Island?
In Bay Island, Florida, there are several family-friendly house rentals available, offering a wonderful retreat for visitors. This charming locale features properties that often include spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for children to play. Many homes also provide amenities like Wi-Fi and air conditioning to ensure a comfortable stay.

Families can enjoy nearby attractions such as the beautiful beaches, where sand and surf provide endless fun, and local parks that offer playgrounds and picnic areas. The area is also close to vibrant dining options and shopping centers, making it easy to explore local culture.
Can I rent a vacation home with a pool or hot tub in Bay Island?
In Bay Island, Florida, travelers will find several vacation homes available for rent that feature both pools and hot tubs. This charming community offers a relaxing atmosphere, with properties often located near the waterfront, providing easy access to beach activities and scenic views. Many rentals come equipped with inviting outdoor spaces, including private pools and hot tubs great for unwinding after a day of exploration.

Guests can also expect amenities such as fully equipped kitchens for preparing meals, spacious living areas for family gatherings, and often outdoor grills for alfresco dining.
Are there any Bay Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bay Island with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
Can I book pet-friendly vacation rentals in Bay Island?
In Bay Island, Florida, there are several pet-friendly vacation rentals available, providing travelers with a great opportunity to enjoy their stay with furry companions. Many of these rentals feature amenities such as spacious backyards, open living areas, and fully equipped kitchens, ensuring comfort for both pets and their owners.

The area is known for its beautiful waterfront views and proximity to local beaches, making it a delightful spot for dog owners who enjoy outdoor activities. Nearby, pet-friendly parks and walking paths offer superb opportunities for strolls and playtime with pets.
Can I find long-stay vacation rentals in Bay Island?
A long-stay vacation rental in Bay Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Bay Island for a vacation rental?
The most popular time to visit Bay Island is from January to March, when the area comes alive with visitors seeking a warm escape during the winter months. During this peak season, travelers flock to enjoy the sun-soaked beaches and vibrant local culture, all while basking in average temperatures ranging from the mid-60s to the low 80s Fahrenheit. This period provides excellent conditions for outdoor activities, such as kayaking, paddleboarding, or simply lounging on the beach.

January, in particular, stands out as a prime month for vacation rentals. With the holiday crowds dissipating, you can enjoy a more relaxed atmosphere while still taking advantage of the pleasant weather. The local attractions, including stunning waterfront parks and charming restaurants, are easily accessible, making it an ideal time for sightseeing and leisurely strolls.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing you to explore Bay Island's natural beauty without the hustle and bustle of peak season. The weather remains mild, superb for enjoying the scenic coastal views and engaging in outdoor activities at a more leisurely pace.
Are there any remote work vacation rentals in Bay Island?
In Bay Island, Florida, there are several vacation rentals that cater to remote work needs. Many of these properties offer amenities such as free Wi-Fi, dedicated workspaces with desks and chairs, and reliable internet connections, ensuring that guests can stay productive while enjoying their stay. The area is known for its serene environment, making it an attractive spot for those looking to balance work and leisure.

Additionally, guests can also enjoy the nearby beaches and local attractions during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Bay Island vacation rental?
Book your Bay Island vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
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 area's natural beauty and recreational opportunities. The nearby Gulf of Mexico offers stunning beaches, superb for sunbathing and water activities like swimming, kayaking, and paddleboarding. The charming waterfront of Madeira Beach is just a short drive away, featuring the popular Johns Pass Village, where visitors can explore shops, restaurants, and take part in dolphin-watching tours.

For those interested in nature, the nearby Fort De Soto Park is a must-visit, known for its pristine beaches, historic fort, and extensive trails for walking and biking. The park also provides opportunities for birdwatching and fishing. In addition, the area boasts vibrant nightlife and dining options with waterfront views, especially in the neighboring communities of Treasure Island and St. Pete Beach, where visitors can savor fresh seafood and enjoy live music.
Can I change or cancel my Bay Island home rental booking on Vrbo?
To find Bay Island vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Bay Island vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

Frequently asked questions

Are there vacation rentals in Bay Island?
Yes, we give you a choice of vacation rentals near well known sights in Bay Island, or you can choose a more remote option if you'd like a relaxing place to stay.
How many vacation rentals will I find in Bay Island?
Choose from 7 Expedia vacation rentals in Bay Island for a memorable vacation.
What can I see and do in Bay Island?
Explore the area and family-friendly sights such as Mote Marine Laboratory & Aquarium, or get out into nature at a spot like Lido Beach. Siesta Key Beach and Marie Selby Botanical Gardens are a couple of places you'll find in the larger area.
What are vacation rentals like in Bay Island?
Vacation rentals are privately owned accommodations you can reserve for a few days or a quick weekend in Bay Island. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.

More Vacation Ideas