Discover Your Perfect Oyster Bay Vacation Homes

Best Vacation Homes in Oyster Bay

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10.0 (183 Reviews)
Cottage
The Inn On Siesta Key
  • Air Conditioner
  • Parking
  • Pet Friendly
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Oyster Bay Pet Friendly Vacation Rentals

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Oyster Bay Large Vacation Homes

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Why Choose Rent By Owner for your Oyster Bay Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals

Where are the best neighborhoods to stay in Oyster Bay?

When choosing a neighborhood to stay in within Oyster Bay, Sarasota, Florida, you'll find an inviting community that offers both tranquility and convenience. This area is perfect for travelers seeking easy access to the scenic beauty and welcoming atmosphere of Sarasota. Whether you're looking for a peaceful retreat or a lively spot close to local amenities, Oyster Bay provides a variety of options for comfortable and reliable vacation rentals. Enjoy the serenity of this charming neighborhood while staying close to everything you need for a memorable Florida getaway.

South Sarasota

This area offers a tranquil setting with easy access to the natural beauty of Sarasota, making it an ideal choice for those seeking a peaceful retreat. Here, you can enjoy proximity to local amenities while experiencing the relaxed atmosphere that defines the region.

View 116+ Rentals in South Sarasota

Best Times to Visit Oyster Bay

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you can enjoy the region's best weather and activities, making your stay in Oyster Bay, Sarasota, Florida, USA, all the more memorable.

Peak Season Highlights

winter
Winter (December to February)

During the winter months, you can enjoy warm weather and pleasant coastal breezes, making this an ideal time for beach activities and outdoor adventures.

Average Temperature Daytime: 75°F - Nighttime: 60°F
spring
Spring (March to May)

Spring transforms this area with blooming flora and mild temperatures, perfect for exploring nature and relaxing by the water.

Average Temperature Daytime: 78°F - Nighttime: 63°F

Off-Season Highlights

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Summer (June to August)

While summer offers warmest weather and vibrant local events, it is also the most crowded period, so booking early is recommended.

Average Temperature Daytime: 88°F - Nighttime: 74°F
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Fall (September to November)

Autumn features cooler temperatures and quieter beaches, providing a peaceful setting for your getaway when crowds are fewer.

Average Temperature Daytime: 80°F - Nighttime: 65°F

Weekly Weather Forecast for Oyster Bay

How to Book Your Oyster Bay Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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 Vacation Rentals in Oyster Bay Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 your stay with access to private outdoor pools, perfect for relaxing under the sun.
  • Benefit from spacious outdoor patios or decks, ideal for entertaining or dining al fresco.
  • Discover beautifully landscaped gardens and lush green spaces surrounding your rental.
  • Take advantage of outdoor grilling areas to prepare delicious meals during your visit.
  • Relax in screened-in porches that let you enjoy the fresh air while keeping pesky insects away.
  • Make the most of nearby tennis courts or pickleball facilities for active recreation.
  • Utilize outdoor recreational setups like shuffleboard or bocce ball courts for added fun.

Top Attractions Around Oyster Bay

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities such as relaxing on beautiful beaches, exploring scenic parks, and engaging in water sports right here in Sarasota's coastal region.

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Family Activities

  • Myakka River State Park: Explore the area's natural beauty by taking a family-friendly airboat tour or enjoying a picnic amid lush landscapes.
  • Sarasota Jungle Gardens: Experience an engaging day with exotic animals, interactive shows, and educational experiences suitable for all ages.
  • Marie Selby Botanical Gardens: Discover tropical plants and vibrant flowers while strolling through beautifully curated gardens along the water.
  • South Lido Park: Relax on pristine beaches, build sandcastles, or enjoy gentle nature walks in this scenic coastal park.
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Adult Activities

  • Exploring the Sarasota Bayfront Park: Enjoy a leisurely stroll or a relaxing afternoon at this scenic waterfront park, offering stunning views and peaceful surroundings.
  • Discovering local art and culture at the Ringling Museum of Art: Immerse yourself in world-class art collections and captivating exhibitions within this cultural landmark nearby.
  • Playing a round of golf at nearby courses: Tee off at expertly maintained golf courses in the region that cater to both beginners and seasoned players alike.
  • Taking a boat tour around Sarasota's waterways: Experience the area's natural beauty and diverse wildlife on guided boat excursions along the tranquil waters.

Oyster Bay Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local outdoor activities: Take advantage of the region’s scenic parks and waterways to enjoy activities like kayaking, fishing, or leisurely walks that showcase the area's natural beauty.
  • Plan your visit around seasonal events: Check for community festivals or cultural events happening during your stay to immerse yourself in the local vibe and make unforgettable memories.
  • Utilize local dining spots: Indulge in authentic regional cuisine at nearby restaurants to experience the flavors that define this destination’s culinary scene.
  • Choose a well-located vacation rental: Select a property close to key attractions and the coastline for easy access and maximize your leisure time here.

Transportation Options

  • Shuttle Services: You can take advantage of local shuttle options that connect you to key spots around the area, ensuring convenient access to Sarasota’s attractions from your vacation rental.
  • Rental Cars: Renting a car provides the freedom to explore all that this region offers at your own pace, with many rental agencies nearby for easy pick-up and drop-off.
  • Public Transit: The local bus system offers an economical way to navigate here, making it simple to reach beaches, shopping centers, and entertainment venues without hassle.
  • Taxi and Ride-Sharing: Taxis and ride-sharing services are readily available in the area, providing quick and dependable transportation when you need to get around efficiently.

Local Customs Options

  • Local Seafood Festivals: Participating in regional seafood festivals allows you to enjoy fresh catches and traditional dishes, celebrating the area's coastal heritage.
  • Gulf Coast Etiquette: It’s customary to adhere to relaxed yet respectful social manners that emphasize friendliness and environmental respect here on the Gulf Coast.
  • Beach Tanning Customs: Embracing the laid-back vibe includes understanding that casual beach attire and sunbathing are integral parts of the seaside culture.
  • Eco-Conscious Practices: Respect for local natural resources is evident through participation in conservation efforts and environmentally friendly activities prevalent in the region.

Frequently Asked Questions About Oyster Bay?

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 vacation rentals have private pools in Oyster Bay?

There are 1428 vacation rentals with private pools near Oyster Bay. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Oyster Bay are best for families?

If you are looking for a family-friendly vacation home in Oyster Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Oyster Bay:

4. 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 7569 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. 

5. What is the cancellation policy for vacation rentals here?

Cancellation policies vary depending on the individual property owner or manager. To understand the specific terms, please review the listing details or contact the property owner directly before booking.

6. Are there any fees I should be aware of when booking a rental in this destination?

Additional fees such as cleaning, service charges, or taxes may apply and are typically outlined in the listing. Be sure to check the detailed description or ask the owner for clarification before confirming your reservation.

7. How do I confirm the availability of my preferred dates?

Availability can fluctuate, so it’s best to verify your dates directly through the listing. If you have questions about open dates, reaching out to the owner can provide the most accurate information.

8. Is it possible to inquire about special requests or additional amenities?

Yes, many hosts are willing to accommodate special requests or provide extra amenities. Contact the property owner prior to booking to discuss any specific needs or preferences.

9. What should I know about check-in and check-out procedures?

Check-in and check-out times vary by property. Details are usually specified in the listing, but contacting the owner beforehand ensures a smooth arrival and departure process during your stay in the area.

Oyster Bay Top Rated Vacation Rentals

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