1. USA
  2. Florida
  3. Sarasota
  4. Bay Island
  5. Rentals by Owner

Discover Your Perfect Bay Island Rentals by Owner

Bay Island Rentals by Owner

More Top-Rated Rentals by Owner in Bay Island Area

Why Choose Rent By Owner for your Bay Island vacation rental?

What makes our Rentals by Owner special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Bay Island Rentals by Owner

Where are the best neighborhoods to stay in Bay Island?

When choosing where to stay in Bay Island, Siesta Key, Florida, you’ll find that the neighborhood offers a charming and relaxed atmosphere ideal for your vacation. This area is perfect if you're seeking convenient access to stunning beaches and local amenities, all while enjoying a comfortable and private rental experience. With Rent By Owner, securing a rental in this sought-after neighborhood ensures a seamless booking process, giving you peace of mind as you prepare for an unforgettable stay in Siesta Key’s beautiful surroundings.

Siesta Key Village

Located close to the heart of Siesta Key, this vibrant neighborhood offers easy access to local shops and cafes, making it an ideal spot for those seeking a lively yet relaxing atmosphere. Here, you can enjoy a convenient stay while exploring the natural beauty of the region.

View 4411+ Rentals in Siesta Key Village

Saint Armands Key

Nestled on a charming barrier island, this area provides a sophisticated setting with upscale shopping and dining options just minutes from your rental. Visitors often choose this neighborhood for its blend of luxury and proximity to the region's stunning beaches.

View 67+ Rentals in Saint Armands Key

The Meadows

Set amidst lush greenery and tranquil surroundings, this neighborhood is perfect if you prefer a peaceful retreat near nature. It offers convenient access to parks and outdoor activities that showcase the best of the area's scenic landscape.

View 60+ Rentals in The Meadows

Central Sarasota

Known for its central location, this part of town places you within easy reach of cultural attractions, shopping districts, and dining experiences, making it a practical choice for exploring the region's diverse offerings.

View 1460+ Rentals in Central Sarasota

Sarasota Springs

A welcoming community with a warm ambiance, this neighborhood provides a comfortable base for enjoying the region’s parks, golf courses, and family-friendly attractions nearby.

View 137+ Rentals in Sarasota Springs

Downtown

Offering a vibrant urban atmosphere, downtown Sarasota is ideal if you want to immerse yourself in the city’s cultural scene, shopping, and nightlife, all within walking distance of your vacation rental.

View 1395+ Rentals in Downtown

Fruitville

This suburban area combines residential comfort with easy access to shopping centers and local amenities, providing a balanced environment for a relaxed yet convenient stay.

View 43+ Rentals in Fruitville

Gulf Gate Estates

Situated close to the coast, this neighborhood offers a laid-back vibe with easy access to the region’s beaches and outdoor recreational spots, perfect for a tranquil seaside retreat.

View 418+ Rentals in Gulf Gate Estates

Best Times to Visit Bay Island

When should you plan your Rentals by Owner stay?

To make the most of your stay, consider planning your vacation during the region's optimal seasons when the weather is ideal and rental options are plentiful, ensuring a memorable experience here in Bay Island, Siesta Key, Florida.

Peak Season Highlights

spring
Spring (March to May)

During the spring months, you can enjoy warm weather and lively beach activities, making it an ideal time for a vacation here. The area tends to be bustling with visitors seeking to experience the vibrant local scene.

Average Temperature Daytime: around 78°F to 85°F - Nighttime: approximately 60°F to 70°F
winter
Winter Holidays (December to February)

The winter season attracts travelers looking to escape colder climates, offering mild temperatures and festive atmosphere. It’s a popular period for those wanting to enjoy serene beaches and comfortable weather in this destination.

Average Temperature Daytime: about 70°F to 75°F - Nighttime: roughly 55°F to 65°F

Off-Season Highlights

image
Summer (June to August)

While summer is typically busy, it also marks the hottest period, so you might find more affordable rental options and fewer crowds. This is the perfect time if you prefer a quieter visit while still enjoying warm waters.

Average Temperature Daytime: around 88°F to 92°F - Nighttime: approximately 75°F to 80°F
image
Early Fall (September to October)

As the region transitions into fall, you may experience lower visitor numbers and better availability of rentals by owner. The weather remains warm enough for beach days, often with less humidity and a more relaxed vibe.

Average Temperature Daytime: about 82°F to 86°F - Nighttime: roughly 65°F to 72°F

Weekly Weather Forecast for Bay Island

How to Book Your Bay Island vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Bay Island

More Top-Rated Rentals by Owner in Bay Island Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

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 a private or shared outdoor pool to unwind after a day at the nearby beaches.
  • Relax in lush landscaped gardens that create a tranquil ambiance within this coastal community.
  • Take advantage of outdoor lounging areas equipped with comfortable furniture for sunbathing or evening gatherings.
  • Utilize outdoor grilling stations or BBQ areas perfect for preparing fresh seafood and local delicacies.
  • Benefit from direct access to the region's pristine beaches, ideal for swimming, sunbathing, or beachcombing.
  • Make use of well-maintained walking paths or bike trails to explore the scenic surroundings of here.
  • Participate in outdoor recreational facilities like tennis courts or volleyball courts available on-site for active fun.

Top Attractions Around Bay Island

What attractions are nearby?

In this vibrant coastal area, you'll find a variety of nearby activities to enjoy, from relaxing on pristine beaches to exploring local parks and engaging in water-based adventures, making it an ideal destination for memorable seaside getaways.

image
image

Family Activities

  • Siesta Key Beach: Enjoy a family day on powdery white sands and gentle surf, perfect for building sandcastles and relaxing by the shoreline.
  • Shelling at Point of Rocks: Explore the natural rock formations and collect unique seashells along this scenic spot, engaging children in a fun outdoor activity here.
  • Pelican Man's Bird Sanctuary: Visit this local sanctuary to observe and learn about native bird species, making it an educational experience for all ages.
  • Sunset Viewing at Siesta Key Village: Gather as a family to witness stunning sunsets over the region while enjoying nearby shops and casual dining options.
image

Adult Activities

  • Snorkeling and Diving: Discover vibrant underwater ecosystems just off the coast, perfect for exploring marine life in this beautiful region.
  • Sunset Cruises: Experience breathtaking sunsets on a scenic boat cruise that highlights the area's stunning coastline views and tranquil waters.
  • Beachfront Relaxation: Unwind along pristine sands with unobstructed views of the Gulf of Mexico, ideal for lounging or engaging in beachside activities.
  • Water Sports Adventures: Engage in kayaking, paddleboarding, or jet skiing to make the most of your visit here with exciting aquatic pursuits.

Other Places to Stay in Bay Island, FL

Bay Isle
Explore 49 Properties
More Places to Stay Near Bay Island

Bay Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for Beach Days: Secure your rental early to ensure access to prime spots on the region’s beautiful beaches, allowing you to enjoy sunbathing and swimming without worry.
  • Explore Local Dining Options: Take advantage of nearby eateries and cafes in the area to experience authentic regional flavors and conveniently complement your stay here.
  • Utilize Water Activities: Make the most of your time by trying out kayaking, paddleboarding, or snorkeling, which are popular ways to enjoy the waters here and discover the area's marine life.
  • Respect Nature and Regulations: Follow local guidelines and environmental practices during your visit to help preserve this destination’s natural beauty for future travelers.

Transportation Options

  • Personal Car Rentals: Renting a car gives you the flexibility to explore this stunning coastal area at your own pace, with many rental agencies available nearby.
  • Public Transportation: The regional bus services provide an affordable and convenient way to travel around here without the hassle of parking or driving.
  • Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily accessible, offering quick transportation to local attractions and neighboring islands.
  • Boat Rentals and Water Taxis: Given the proximity to waterways, renting a boat or using water taxis offers a scenic and enjoyable way to experience the area from the water.

Local Customs Options

  • Respect for Local Marine Life: When visiting the coastal areas, you are encouraged to observe wildlife without disturbing the natural habitat, reflecting the community’s commitment to preserving its marine environment.
  • Beach Etiquette: Here, it’s customary to keep your space clean by disposing of trash properly and following guidelines for beach use, ensuring an enjoyable experience for everyone.
  • Photography Norms: Taking photos of local residents or their property is generally discouraged unless explicitly permitted, respecting privacy in this scenic region.
  • Harbor and Boating Customs: When engaging in boating activities, adhere to local navigation rules and safety practices to ensure smooth interactions on the water.

Frequently Asked Questions About Bay Island Rentals by Owner

1. What are the top vacation rentals in Bay Island?

There are a lot of options in Bay Island. If you plan on staying in the Bay Island 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 Island:

2. How many Rentbyowner vacation rentals are available in Bay Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 60 in the Bay Island 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 Island. 

3. What is the cancellation policy for a rental by owner in this destination?

The cancellation policy varies depending on the individual listing. You should review the specific rental's cancellation terms on the listing page or contact the owner directly to understand the conditions and any applicable fees.

4. Are there any additional fees I should be aware of when booking a rental in this area?

Additional fees such as cleaning, service charges, or security deposits may apply and are detailed in each rental listing. It’s recommended to read the full description or reach out to the owner for clarification before completing your booking.

5. How do I find and confirm availability for the rental I am interested in?

Availability can be checked directly through the listing on the booking platform, where you can see open dates. Confirm with the owner if you have specific questions about the property’s availability or need special arrangements.

6. What amenities are typically included in rentals by owner here?

Amenities vary between listings but often include essentials like Wi-Fi, kitchen facilities, and parking. To ensure the rental meets your needs, review the amenities listed on the property page or contact the owner for more details.

7. What steps should I take to ensure a smooth check-in process in this region?

Check the specific check-in instructions provided by the owner in the listing, which may include key pickup procedures or access codes. Communicate with the owner ahead of your arrival to clarify any details and ensure a seamless check-in experience.

More Rentals You May Like Near Bay Island

More Top-Rated Rentals by Owner in Bay Island Area