Discover Your Perfect Glen Oaks Vacation Homes

Best Vacation Homes in Glen Oaks

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10.0 (1 Review)
House
Sunshine Tiny Home Pinecraft
  • Air Conditioner
  • Parking
  • Security/Safety
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Glen Oaks Luxury Rentals

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Glen Oaks Pet Friendly Vacation Rentals

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Glen Oaks Large Vacation Homes

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8.8 (6 Reviews)
House
Alta Vista Respite
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
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Why Choose Rent By Owner for your Glen Oaks 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 Glen Oaks Vacation Rentals

Where are the best neighborhoods to stay in Glen Oaks?

When selecting the perfect neighborhood to stay in Sarasota, Florida, Glen Oaks offers a tranquil and welcoming environment ideal for your vacation. Located conveniently within the city, this area provides easy access to local amenities and scenic surroundings, making it an excellent choice for those seeking a relaxed yet connected experience. Whether you prefer a quiet retreat or a central spot to explore the broader Sarasota region, Glen Oaks provides a dependable and comfortable setting for your stay. Trust in quality vacation rentals here to ensure a seamless and enjoyable trip to Sarasota's charming neighborhoods.

Kensington Park

In this charming neighborhood, you can enjoy the peaceful atmosphere while being close to Sarasota's vibrant attractions. It’s an ideal area for those seeking comfortable and convenient vacation rentals in a serene setting.

View 1022+ Rentals in Kensington Park

Best Times to Visit Glen Oaks

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you experience the region’s best weather and activity offerings, making your stay in Sarasota’s Glen Oaks area truly memorable.

Peak Season Highlights

winter
Winter (December to February)

During winter, you can enjoy the warm climate of this destination, making it an ideal time to explore outdoor activities and relax in the pleasant weather.

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

Spring offers mild temperatures and blooming landscapes, encouraging you to indulge in outdoor adventures and experience the area's lively atmosphere.

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

Off-Season Highlights

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Summer (June to August)

In summer, you might encounter hotter days with higher humidity, which is perfect if you're seeking sunbathing or water-based activities by the region's beaches.

Average Temperature Daytime: 88°F - Nighttime: 75°F
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Fall (September to November)

Fall brings cooler temperatures and fewer crowds, providing a peaceful setting to enjoy the natural beauty and tranquility here.

Average Temperature Daytime: 78°F - Nighttime: 65°F

Weekly Weather Forecast for Glen Oaks

How to Book Your Glen Oaks 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 Glen Oaks

More Top-Rated Vacation Rentals in Glen Oaks 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 outdoor swimming pools available at many properties, perfect for relaxing under the Florida sun.
  • Take advantage of private or shared patios and decks to unwind and soak in the scenic surroundings.
  • Benefit from lush, landscaped gardens that enhance your outdoor living experience.
  • Make use of outdoor grilling facilities to host barbecues and gatherings with friends and family.
  • Relax on spacious outdoor furniture designed for comfort and leisure during your stay.
  • Utilize nearby walking trails or biking paths that allow you to explore the natural beauty of the region.
  • Access well-maintained tennis courts or other sports amenities often featured in the area’s vacation rentals.

Top Attractions Around Glen Oaks

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of outdoor activities, scenic beaches, and cultural attractions just a short drive from your vacation rental in Sarasota, offering an ideal backdrop for relaxation and exploration.

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Family Activities

  • Sarasota Jungle Gardens: Discover the vibrant local wildlife at this family-friendly attraction, offering engaging animal encounters and lush botanical gardens right in the region.
  • Myakka River State Park: Enjoy scenic outdoor adventures such as boat tours, nature walks, and wildlife viewing in this expansive park that showcases the natural beauty of here.
  • The Ringling Museum of Art: Introduce your family to art and culture at this renowned Sarasota museum, featuring captivating exhibits and beautiful grounds just a short drive away.
  • Siesta Key Beach: Relax and play on one of Florida’s most famous beaches, known for its soft white sands and family-friendly swimming spots close to here.
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Adult Activities

  • Golfing at The Legacy Golf Club: Enjoy a round of golf on the scenic courses that showcase the region’s lush landscapes and well-maintained fairways, perfect for a relaxing day in the area.
  • Exploring Marie Selby Botanical Gardens: Immerse yourself in the breathtaking plant displays and tranquil settings that highlight the natural beauty of Sarasota's botanical garden oasis.
  • Sailing and Water Sports: Take advantage of the nearby Gulf Coast waters for sailing, paddleboarding, or kayaking and experience the region’s stunning coastline firsthand.
  • Dining at Local Cuisine Spots: Savor fresh seafood and regional delicacies at charming restaurants that reflect the culinary spirit of this popular Florida destination.

Glen Oaks Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining options: Take advantage of the region’s diverse culinary scene to enjoy authentic flavors and make your stay more memorable.
  • Plan outdoor activities: Utilize nearby parks and scenic spots to experience the natural beauty that makes this destination unique.
  • Visit nearby beaches: Relax on pristine shores or take part in water sports to fully enjoy the coastal charm of this area.
  • Discover cultural experiences: Engage with local arts and community events to immerse yourself in the vibrant atmosphere here.

Transportation Options

  • Rental Car Services: You can conveniently access major rental car providers in the area to explore Sarasota and its surroundings at your own pace.
  • Public Transit: The local bus system offers an affordable and reliable way to travel around here and reach nearby attractions within the region.
  • Taxi and Rideshare: Taxis and rideshare options like Uber and Lyft are readily available for quick, direct trips throughout the destination.
  • Shuttle Services: Several shuttle services operate in this part of Florida, providing easy transportation between the airport and your preferred accommodation here.

Local Customs Options

  • Southern Hospitality: You will often notice the warm and friendly greeting that exemplifies the region's reputation for Southern hospitality in this part of Sarasota.
  • Local Fishing Etiquette: Engaging in fishing here involves respecting local regulations and practicing catch-and-release to preserve the area's aquatic life.
  • Community Events: Participating in neighborhood gatherings or outdoor festivals provides an authentic glimpse into the area's rich cultural traditions.
  • Gardening Customs: Many residents take pride in maintaining lush, native plant gardens that reflect the region’s tropical climate and eco-conscious values.

Frequently Asked Questions About Glen Oaks?

1. What are the top vacation rentals in Glen Oaks?

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

2. How many vacation rentals have private pools in Glen Oaks?

There are 250 vacation rentals with private pools near Glen Oaks. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Glen Oaks are best for families?

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

4. How many Rentbyowner vacation rentals are available in Glen Oaks?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1320 in the Glen Oaks 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 Glen Oaks. 

5. What is the cancellation policy for vacation rentals in this area?

The cancellation policy varies by property. You should review the specific listing details or contact the property owner directly to understand the terms related to cancellations and potential refunds.

6. How do I know if my preferred dates are available for booking?

Availability depends on the individual property’s calendar. Check the listing online or reach out to the owner for real-time availability and to confirm your desired dates.

7. Are there any additional fees I should be aware of when booking here?

Additional fees such as cleaning, service charges, or taxes may apply. These are outlined in the listing details, but it’s best to verify with the property owner before finalizing your reservation.

8. What amenities are typically included in vacation rentals in this region?

Most properties offer essential amenities like Wi-Fi, parking, and kitchen facilities, but offerings can differ. Review each listing carefully to ensure it meets your needs or contact the owner for specific questions.

9. How do I contact the property owner if I have questions after booking?

You can use the messaging system provided on the booking platform to communicate directly with the property owner. They can assist with any additional questions about your stay or the property itself.

Glen Oaks Top Rated Vacation Rentals

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10.0 (2014 Reviews)
Hotel
Carlisle Inn
  • Air Conditioner
  • Parking
  • Pool
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10.0 (34 Reviews)
House
A Whale of a Good Time!
  • Air Conditioner
  • Parking
  • Pet Friendly
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