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  3. Sarasota
  4. Oyster Bay
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Discover Your Perfect Oyster Bay Rentals by Owner

Oyster Bay Rentals by Owner

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10.0 (9 Reviews)
Apartment
Casa Limonada Boutique Motel
  • Air Conditioner
  • View
  • Ocean View
View Availability
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10.0 (4 Reviews)
Villa
Lido Beach Villa
  • Air Conditioner
  • Parking
  • Pool
View Availability
More Top-Rated Rentals by Owner in Oyster Bay Area

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

What makes our Rentals by Owner special?

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

Popular Areas for Oyster Bay Rentals by Owner

Where are the best neighborhoods to stay in Oyster Bay?

When choosing a place to stay in Sarasota, Florida, exploring the neighborhoods around Oyster Bay offers you a blend of tranquility and convenient access to local amenities. Each neighborhood provides a unique atmosphere, whether you prefer a peaceful retreat or a vibrant community setting. Booking a rental by owner in this area ensures you enjoy a dependable and seamless experience, allowing you to focus on discovering all that Sarasota has to offer. From scenic quiet streets to lively residential areas, these neighborhoods are ideal for those seeking comfort and convenience during their visit to Sarasota, Florida.

South Sarasota

In this part of the region, you’ll find an inviting atmosphere perfect for relaxing getaways. Staying here offers convenient access to local amenities and a peaceful environment, making it an ideal choice for your stay.

View 116+ Rentals in South Sarasota

Best Times to Visit Oyster Bay

When should you plan your Rentals by Owner stay?

To make the most of your stay here, consider visiting during the shoulder seasons when the weather is pleasant and rental rates are more affordable, allowing you to enjoy the region's serene environment without the peak season crowds.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, the area experiences warm and pleasant weather, making it an ideal time for outdoor activities and enjoying the beaches.

Average Temperature Daytime: 75°F - Nighttime: 55°F
spring
Spring (March to May)

Spring brings mild temperatures and blooming landscapes, attracting visitors seeking a vibrant yet comfortable environment in this coastal region.

Average Temperature Daytime: 80°F - Nighttime: 60°F

Off-Season Highlights

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Summer (June to August)

The summer season offers hotter temperatures and higher humidity, which might be ideal for beachgoers looking to fully enjoy the waters and sunshine here.

Average Temperature Daytime: 88°F - Nighttime: 72°F
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Fall (September to November)

Autumn features slightly cooler temperatures and less crowded conditions, providing a peaceful opportunity to explore and relax in the area.

Average Temperature Daytime: 78°F - Nighttime: 58°F

Weekly Weather Forecast for Oyster Bay

How to Book Your Oyster Bay 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 Oyster Bay

More Top-Rated Rentals by Owner in Oyster Bay 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 outdoor lounging areas with chairs and tables for relaxing in the sunshine.
  • Take advantage of private pools or access to community swimming facilities for refreshing dips.
  • Benefit from well-maintained outdoor grills or barbecue stations perfect for preparing meals al fresco.
  • Make use of expansive patios or decks ideal for outdoor dining and entertaining guests.
  • Experience the convenience of lush, landscaped gardens or yard spaces for outdoor activities.
  • Utilize outdoor shower amenities, especially if your stay involves water-based pursuits in the area.
  • Relax in shaded pergolas or gazebo structures designed for restful retreats amidst tropical surroundings.

Top Attractions Around Oyster Bay

What attractions are nearby?

In this vibrant area, you can enjoy a variety of outdoor activities, including scenic walks along the waterfront and exploring local parks, all just moments from your rental by owner in Oyster Bay, Sarasota, Florida.

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Family Activities

  • Myakka River State Park: Explore the region's natural beauty with a family-friendly tram tour or a scenic hike through lush landscapes and diverse wildlife.
  • South Lido Park: Enjoy a day at this nearby park, perfect for picnicking, bird watching, and relaxing on pristine beaches with your loved ones.
  • Big Sarasota Pass: Embark on a boat trip or paddleboarding adventure to appreciate the area's coastal ecosystem and observe marine life in its natural habitat.
  • John and Mable Ringling Museum of Art: Experience cultural enrichment as a family by visiting this renowned museum showcasing impressive European artwork in a beautiful setting.
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Adult Activities

  • Sailing and Boating: Explore the waters surrounding this destination with a relaxing sailing or boat tour, offering spectacular views of the Gulf Coast and a chance to unwind on the water.
  • Golfing: Enjoy a round at one of the premier golf courses in the region, where lush fairways and scenic landscapes await to challenge your skills and provide a tranquil escape.
  • Wildlife Watching: Visit local parks and nature reserves to observe diverse bird species and coastal wildlife, perfect for outdoor enthusiasts seeking peaceful exploration.
  • Dining Experiences: Indulge in the area's renowned restaurants featuring fresh seafood and regional cuisine, ideal for savoring authentic flavors in a relaxed setting.

Oyster Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Events and Markets: Take advantage of nearby markets and community events to experience the authentic vibe and support local businesses in the area.
  • Plan Outdoor Activities: Make the most of the region’s pleasant weather by scheduling outdoor adventures like beach visits or nature walks right from your rental accommodation.
  • Utilize Nearby Amenities: Choose a rental that offers convenient access to essential amenities, ensuring a comfortable and hassle-free stay in this coastal destination.
  • Connect with Your Hosts: Communicate with your rental hosts for insider tips on hidden gems and the best ways to enjoy your time here, elevating your overall experience.

Transportation Options

  • Car Rentals: Renting a vehicle here offers the flexibility to explore the area's charming neighborhoods and scenic coastal routes at your own pace.
  • Public Transit: The regional bus services provide an affordable and reliable way to navigate the region's key destinations without the hassle of parking.
  • Taxi and Rideshare Services: Convenient options like taxis and rideshare apps ensure you can easily access local attractions and amenities whenever needed.
  • Bicycle Rentals: Biking is an enjoyable and eco-friendly way to experience the tranquil surroundings and scenic paths in this part of Sarasota County.

Local Customs Options

  • Respect for Local Waterfront Etiquette: You’ll find that maintaining quiet and orderly behavior near the region’s waterways is appreciated by residents and visitors alike.
  • Celebration of Regional Art and Craftsmanship: Participating in or observing local art festivals showcases the area's appreciation for Sarasota's rich cultural heritage.
  • Environmental Conservation Practices: The community values sustainable practices, so be mindful of preserving the natural beauty that makes this destination unique.
  • Greeting Customs and Hospitality: Warm and friendly interactions are typical here, reflecting the welcoming spirit of those who call this part of Florida home.

Frequently Asked Questions About Oyster Bay Rentals by Owner

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

There are a lot of options in Oyster Bay. If you plan on staying in the Oyster Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Oyster Bay:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 4352 in the Oyster Bay 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 Oyster Bay. 

3. What is the cancellation policy for a rental by owner in Oyster Bay?

The cancellation policy varies by listing. Please review the specific rental's terms on the listing page or contact the owner directly to understand the conditions and potential fees associated with cancellations.

4. How do I contact the property owner for special requests or questions about my stay?

You can reach out to the property owner through the messaging platform provided on the booking website. They are typically responsive and can assist with special requests or additional information about your stay here.

5. 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. These details are usually listed on the property page, but it’s best to confirm with the owner before completing your reservation.

6. What amenities are generally included in rentals by owner in this region?

Most rentals by owner in this destination offer amenities like Wi-Fi, parking, kitchen facilities, and laundry options. To see what’s included for a specific property, please check the listing details or contact the owner directly.

7. Is it possible to extend my stay at a rental in Oyster Bay if I wish to stay longer?

Availability for extending your stay depends on other bookings. You should contact the property owner as early as possible through the booking platform to discuss extension options and availability.

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More Top-Rated Rentals by Owner in Oyster Bay Area