Bay Isles vacation rentals

We found 297 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Bay Isles to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the amenities you need and want for your stay, which might include WiFi and a washer and dryer. No matter what you're looking for, you'll be able to choose a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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 Isles

Why visit Bay Isles

  • Family-friendly beach fun: Enjoy relaxing days at the Bay Isles Beach Club, perfect for families.
  • Outdoor activities: Explore nearby marinas for boating, fishing, and other outdoor adventures.
  • Scenic beauty: Take in the stunning views of Longboat Key's pristine beaches and lush surroundings.
  • Cozy accommodations: Choose from a variety of vacation rentals, including condos and private homes.
  • Charming community: Experience the friendly locals and vibrant atmosphere of the Bay Isles neighborhood.

Popular types of accommodation around Bay Isles

Planning a getaway to Bay Isles? You’re in for a treat. This stunning destination offers a variety of vacation rentals, including cozy condos, spacious private homes, and comfortable apartments. Whether you prefer the serene Fairway Bay, a beautiful waterfront residence, or access to a private beach, Bay Isles has the perfect spot for you. Discover your ideal home away from home and enjoy the breathtaking Bay Isles Harbor during your stay.

  • Condos: The top choice for vacation rentals in Bay Isles, offering modern amenities and beautiful views.
  • Houses: A popular option for families or groups seeking spacious and comfortable accommodations.
  • Apartments: Ideal for travelers looking for convenient and budget-friendly stays in the area.
  • Cottages: A charming and cozy alternative, perfect for those seeking a quaint getaway.
  • Villas: Luxurious and spacious, these rentals provide an upscale experience for discerning travelers.**

Top attractions near Bay Isles

Bay Isles, Longboat Key, is perfect for family vacations, offering a blend of beach relaxation and city exploration. Key attractions include the Bay Isles Beach Club and nearby marinas, providing outdoor activities and family-friendly experiences. Visitors can enjoy the scenic beauty of Longboat Key while exploring modern amenities and local charm, making it an ideal destination for those seeking both adventure and leisure.

  • Lido Beach: Enjoy the pristine sandy shores and stunning sunsets at Lido Beach, just 6 miles from Bay Isles. This picturesque beach offers a relaxing atmosphere, perfect for sunbathing, swimming, or beachcombing along the gentle waves.
  • IMG Academy: Located 4 miles away, IMG Academy is a premier sports training facility. Experience world-class coaching and facilities in a variety of sports, making it a unique destination for sports enthusiasts.
  • St. Armands Circle: Just 5 miles from Bay Isles, this vibrant shopping and dining district features elegant boutiques and gourmet restaurants, creating a lively city vibe that’s perfect for leisurely strolls and socializing.

Things to do recommended for couples

Planning a romantic getaway in Bay Isles? Enjoy a delightful evening at the Beatrice Friedman Symphony Center, just 5 miles away, or indulge in a couple's treatment at Aluna Wellness Center & Spa, located 8 miles from your stay. For some fun, try mini-golf at Smugglers Cove Adventure Golf, 6 miles away.

Things to do recommended for families

Families visiting Bay Isles can enjoy exciting games at Ed Smith Stadium and LECOM Park, both offering vibrant sports atmospheres. For some relaxation, the Robert L. Taylor Community Complex provides a great space for wellness activities, just a short drive away from the beach.

Things to do recommended for groups

Groups visiting Bay Isles can enjoy a captivating performance at the Van Wezel Performing Arts Hall, embark on an adventurous hike along the scenic Sarasota BayWalk, and engage in some friendly competition at the Longboat Key Public Tennis Center for an unforgettable local experience.

*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 Isles

If you're traveling with a group, family, or pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Bay Isles with a group: Think about how many bedrooms you'll require, as well as any additional features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Bay Isles with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Bay Isles: For many families, a vacation wouldn't feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and pet beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Bay Isles: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Bay Isles

Explore the serene beauty of Bay Isles, Longboat Key, where family-friendly beach vacations meet the charm of coastal living. This barrier island offers a relaxing atmosphere with friendly locals, making it ideal for both budget and business travelers. Discover nearby Sarasota Islands and enjoy the pristine beaches, lush surroundings, and vibrant community. Bay Isles promises unforgettable experiences, perfect for creating lasting memories with family and friends.

  • Sarasota: Located 6 miles from Bay Isles, Sarasota is a vibrant city known for its beautiful beaches and rich cultural scene. Travelers flock to Sarasota for both beach and family-themed experiences. The city boasts a variety of attractions, including shopping malls and resorts, making it perfect for those seeking leisure and entertainment. Visitors can enjoy the stunning local beaches, explore family-friendly neighborhoods, and engage in outdoor activities, all framed by the scenic beauty of the Gulf Coast.
  • Siesta Key: Siesta Key, situated 8 miles from Bay Isles, is a picturesque island renowned for its powdery white sand beaches and serene outdoor atmosphere. This idyllic destination is perfect for families and outdoor enthusiasts alike. Popular attractions include recreational areas, shopping malls, and resorts. Siesta Key offers a laid-back vibe, where you can soak up the sun on the beach, enjoy water sports, and explore charming local shops and eateries, making it a must-visit for nature lovers and beachgoers.
  • Longboat Key: Longboat Key is an enchanting island where Bay Isles is located, offering a mix of beach, family, and city-themed experiences. Just a stone's throw away from Sarasota, this community features shopping centers, recreational areas, and pristine beaches. Visitors can unwind on family-friendly beaches, enjoy the local town's charm, and partake in various activities, ensuring a delightful stay for all ages. Longboat Key is a tranquil escape that combines the beauty of nature with the conveniences of city living.

Best time to go to Bay Isles

If you're planning a trip to Bay Isles, 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
February65.5°F (18.6°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March68.4°F (20.2°C)Light RainMostly SunnyModerately HighSlightly High
April73.8°F (23.2°C)Light RainMostly SunnyAverageSlightly High
May78.1°F (25.6°C)Light RainMostly SunnyAverageAverage
June82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
July83.1°F (28.4°C)Moderate RainMostly SunnyModerately HighSlightly High
August83.5°F (28.6°C)Moderate RainMostly SunnyAverageAverage
September81.5°F (27.5°C)Moderate RainMostly SunnyModerately LowSlightly Low
October77.0°F (25.0°C)Light RainMostly SunnyModerately LowSlightly Low
November70.5°F (21.4°C)Light RainMostly SunnyModerately LowAverage
December66.4°F (19.1°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay can often result in significant 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

Plan your group getaway with an eligible Vrbo and enjoy the benefits of earning OneKeyCash on your reservation. Being the planner truly pays off. When you join our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up now and begin your journey to savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a helpful platform for organizing your travel plans. You can easily create new trips, resume your previous ones, or manage your existing itineraries. All your saved or booked properties are neatly organized under categories like Potential, Upcoming, and Current Trips. To begin utilizing Trip Boards, simply go to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Bay Isles?
In Bay Isles, condos are a popular choice among travelers, with several available in this picturesque area. These condos typically feature modern amenities such as fully equipped kitchens, spacious living areas, and access to community facilities like swimming pools and fitness centers. Many are located near the beach, allowing guests to enjoy the coastal lifestyle seamlessly.

In addition to condos, there are also several vacation houses and villas, which appeal to families or larger groups seeking more space. These properties often boast private yards or patios, multiple bedrooms, and amenities that might include outdoor grills and hot tubs.
Are there any beach house rentals in Bay Isles?
In Bay Isles, Florida, there are approximately 34 beach house rentals available, primarily situated in desirable coastal neighborhoods. These vacation homes typically feature spacious layouts with multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as patios or balconies for enjoying the warm Florida weather. Many properties offer amenities like swimming pools, access to nearby beaches, and proximity to local attractions such as the beautiful Gulf of Mexico and nearby shopping and dining options.
How much does it cost to rent a vacation home in Bay Isles?
Prices for vacation rentals in Bay Isles 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 Isles 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 Isles vacation house rentals?
You can find great discounts on house rentals in Bay Isles 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 Isles?
In Bay Isles, popular vacation rental amenities include heated pools, shared pools, fully equipped kitchens, and coffee and tea makers. These amenities cater to travelers seeking comfort and convenience during their stay. Many rentals are situated in proximity to scenic views and local attractions, enhancing the overall vacation experience.
Are there any family house rentals in Bay Isles?
In Bay Isles, Florida, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. This picturesque area features spacious homes equipped with amenities that cater to families, including full kitchens for preparing meals and ample living spaces for relaxation and gatherings. Many properties also offer outdoor areas, such as private pools or patios, where kids can enjoy some fun in the sun.

Visitors will find themselves in close proximity to beautiful beaches, great for family outings, and local parks that provide playgrounds and recreational facilities. The nearby Gulf of Mexico adds to the charm, offering opportunities for water activities and exploration.
Can I rent a vacation home with a pool or hot tub in Bay Isles?
In Bay Isles, Florida, there are several vacation homes available for rent that feature both pools and hot tubs, with around 11 options to choose from. This beautiful coastal community offers a serene atmosphere and is conveniently located near the stunning beaches of Longboat Key. Travelers can expect a variety of amenities in these rentals, including private pools, relaxing hot tubs, and spacious outdoor areas superb for entertaining or enjoying the Florida sunshine. Many properties also come with fully equipped kitchens, comfortable living spaces, and easy access to local attractions, making them ideal for families or groups looking for a relaxing getaway.
Are there any Bay Isles vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Bay Isles 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 find long-stay vacation rentals in Bay Isles?
A long-stay vacation rental in Bay Isles 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 Isles for a vacation rental?
The best time to visit Bay Isles for a vacation rental is during the peak season from February to April, with March being particularly popular among travelers seeking sun and relaxation. This period offers beautiful weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit, ideal for enjoying the area's stunning beaches and outdoor activities. Visitors can partake in a variety of water sports, such as kayaking or paddleboarding, while also taking advantage of the vibrant local dining scene.

As the winter crowds flock to Bay Isles, you'll find an array of events and festivals that celebrate the region's unique culture and natural beauty. Whether you're lounging by the beach or exploring the picturesque coastal paths, there's no shortage of activities to keep you entertained.

For those looking for a more budget-friendly option, consider visiting in November. This month offers pleasant weather and fewer tourists, allowing for a more tranquil experience while still enjoying the beautiful surroundings. The quieter beaches and local attractions provide a great opportunity for relaxation and exploration without the hustle and bustle of the peak season.

Ultimately, your choice of when to visit Bay Isles will depend on whether you prefer the vibrant energy of the peak season or the peaceful charm of the shoulder months.
Are there any remote work vacation rentals in Bay Isles?
In Bay Isles, Florida, there are several remote work vacation rentals available, with a total of 11 options to choose from. This picturesque area, known for its beautiful waterways and proximity to the Gulf of Mexico, offers a tranquil setting for those looking to balance work and leisure. Travelers can expect properties equipped with amenities that cater to remote work needs, such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs.

In addition to the practical work-related features, many rentals feature inviting living areas, fully equipped kitchens, and outdoor spaces great for relaxation after a day of work. The nearby beaches and local parks provide opportunities for outdoor activities, making it a great location to unwind. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Bay Isles vacation rental?
Book your Bay Isles 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.
Can I change or cancel my Bay Isles home rental booking on Vrbo?
To find Bay Isles 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 Isles 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.

More Vacation Ideas