Discover Your Ideal Longboat Key, Florida, USA Vacation Rental in the Beautiful Bay Isles Area
Discover Your Perfect Bay Isles Vacation Homes
Best Vacation Homes in Bay Isles
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Security/Safety
- Wellness Facilities
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Bay Isles Luxury Rentals
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
Bay Isles Pet Friendly Vacation Rentals
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Pet Friendly
- Pool
- Parking
- Pet Friendly
- View
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- Pet Friendly
Bay Isles Large Vacation Homes
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Pet Friendly
- Security/Safety
- Air Conditioner
- Parking
- Pool
Why Choose Rent By Owner for your Bay Isles Vacation Rental Homes?
What makes our Vacation Rentals special?
Best Times to Visit Bay Isles
When should you plan your Vacation Rentals stay?
Timing your visit to this destination can enhance your experience, as the region offers optimal weather and fewer crowds during certain seasons, making it ideal for securing the perfect vacation rentals here.
Peak Season Highlights
Winter (December to February)
During this peak season, the area experiences warm and sunny days, making it an ideal time for outdoor activities and beach relaxation. The region's inviting climate attracts visitors seeking a comfortable escape from colder climates.
Spring (March to May)
Spring brings pleasant weather and vibrant scenery, drawing travelers to enjoy the scenic beauty and outdoor attractions of this coastal destination. It’s a popular time for those looking to escape early summer crowds.
Off-Season Highlights
Summer (June to August)
The summer months tend to be less busy, offering a quieter experience along the coast while still providing warm temperatures perfect for beach outings. This is an excellent period for travelers seeking lower rates and tranquility.
Fall (September to November)
Autumn sees fewer visitors, with cooler temperatures and occasional rains, creating an ideal setting for peaceful getaways. Accommodation options are more accessible during this off-peak time, making it a smart choice for budget-conscious travelers.
Weekly Weather Forecast for Bay Isles
How to Book Your Bay Isles Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Bay Isles
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private or community swimming pools, perfect for relaxing outdoors in the region’s warm climate.
- Take advantage of spacious outdoor patios or decks ideal for dining al fresco while soaking up the sun.
- Benefit from beautifully maintained gardens and lush landscaping that enhance your outdoor experience here.
- Utilize outdoor grills and barbecue areas to prepare delicious meals amidst scenic surroundings.
- Make use of dedicated outdoor shower facilities, especially if you enjoy beach activities in this popular destination.
- Relax by on-site lakes, ponds, or water features that add tranquility to your stay in this coastal area.
- Access well-equipped outdoor recreational amenities such as tennis courts or walking trails exclusive to the property community.
Top Attractions Around Bay Isles
What attractions are nearby?
In this inviting destination, you can explore nearby golf courses, indulge in water sports on the pristine beaches, or enjoy scenic boat tours just moments from your accommodations.

Family Activities
- Suncoast Beach Yoga & Wellness: Experience family-friendly yoga classes and wellness sessions along the scenic shores of Longboat Key, perfect for relaxing together as a family.
- Longboat Key Turtle Watch: Participate in guided turtle nesting and hatchling releases during the season, offering an educational adventure for children and adults alike.
- Marina Activities at Longboat Pass: Enjoy kayaking, paddleboarding, or boat rentals from the marina to explore the calm waters and observe local marine life with your loved ones.
- Coquina Beach Park: Spend a day building sandcastles, swimming, or picnicking at this family-friendly beach park known for its soft sands and gentle waves.
Adult Activities
- Golfing at Longboat Key Club: Enjoy a round of golf at one of the area's premier courses, renowned for its scenic links and challenging layouts.
- Sailing and boating adventures: Explore the calm waters surrounding this destination with private sailing or boat rentals to experience the region's natural beauty from the water.
- Fine dining experiences: Indulge in exquisite cuisine at local restaurants that showcase fresh seafood and regional flavors, perfect for relaxing evenings.
- Spa and wellness retreats: Unwind and rejuvenate at luxurious spas offering treatments designed to enhance your relaxation during your stay here.
Bay Isles Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local beaches: Make the most of your stay by relaxing on the pristine sands and enjoying the stunning coastal views that define this destination's charm.
- Plan water-based activities: Take advantage of the area's calm waters with kayaking, paddleboarding, or boat rentals to experience the region from a different perspective.
- Visit nearby dining options: Savor fresh seafood and regional specialties at the restaurants close to your vacation rental, immersing yourself in the local culinary scene.
- Utilize local resources: Connect with community centers or concierge services for personalized recommendations to enhance your experience here.
Transportation Options
- Personal Vehicles: Renting a car offers the flexibility to explore the region at your own pace, with several rental agencies conveniently located nearby.
- Public Transit: The area is serviced by local bus routes that provide an affordable way to reach popular destinations within Longboat Key and surrounding areas.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick, convenient transportation around this coastal destination.
- Bicycle Rentals: Biking is a popular choice here, with various bike rental shops offering easy access to scenic routes along the Gulf Coast.
Local Customs Options
- Respect for Local Conservation Laws: You will find that preserving the natural beauty of the area is highly valued, and adhering to guidelines for wildlife and environmental conservation is essential during your stay.
- Greetings with Courtesy: In this tranquil destination, a friendly nod or a polite handshake is customary when meeting new neighbors or local residents.
- Celebration of Community Events: Participating in or observing traditional community gatherings and local festivals offers insight into the area's rich cultural heritage.
- Coffee and Casual Conversations: Engaging in relaxed chats over coffee at neighborhood spots reflects the region’s friendly and laid-back social customs.
Frequently Asked Questions About Bay Isles?
1. What are the top vacation rentals in Bay Isles?
There are a lot of options in Bay Isles. If you plan on staying in the Bay Isles area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Bay Isles:
- Flash sale Sept 2-4/7-13, 5-floor penthouse 60 feet from water, 150+ reviews
- Flash Sale Late Sept-early Oct Take a Peek 1fabulous unit.
- Flash sale late, August/September 50 ft from sand, Private Island 125 +review
- Major Upgrades 1 of a kind home right on the beach
- Condo with a View 1: Top Floor, Oceanview!
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- Client texted view crazy
- THE BEACH #107 Summer special 210 nite+fees Beachfront Full View
- Unit #218 Sand Cay Beach Resort Gulf Front
- Waterfront Coastal 3 BR/3 BTH w/Pool, 50ft. Boat Dock, Walk to Beach
2. How many vacation rentals have private pools in Bay Isles?
There are 76 vacation rentals with private pools near Bay Isles. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Bay Isles are best for families?
If you are looking for a family-friendly vacation home in Bay Isles, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Bay Isles:
4. How many Rentbyowner vacation rentals are available in Bay Isles?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 743 in the Bay Isles area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Bay Isles.
5. What is the cancellation policy for vacation rentals in this area?
6. Are there any specific check-in and check-out procedures I should be aware of?
7. How do I ensure my reservation is secure when booking a vacation rental here?
8. What amenities are typically included with vacation rentals in this destination?
9. Is there a minimum stay requirement for reserving a vacation rental in this region?
Bay Isles Top Rated Vacation Rentals
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pool
- Air Conditioner
- Parking
- Pet Friendly