Discover Your Perfect Odessa Vacation Homes

Odessa Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Odessa 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 Odessa Vacation Rentals

Where are the best neighborhoods to stay in Odessa?

When exploring Odessa, Florida, choosing the right neighborhood can significantly enhance your stay. Whether you're seeking a peaceful retreat or easy access to local amenities, the area offers diverse neighborhoods that cater to various preferences. Located conveniently within the Tampa Bay area, Odessa provides a serene environment while remaining close to vibrant attractions and scenic parks. By selecting a strategic location within Odessa, you can enjoy a comfortable and memorable vacation experience, all while enjoying the reliable and trustworthy options for vacation rentals available nearby.

Lake Keystone

Nestled near the tranquil waters of Lake Keystone, this area offers serene surroundings and scenic views, making it an ideal choice for those seeking a peaceful retreat in Odessa. You’ll enjoy easy access to outdoor activities while staying close to the region’s attractions.

View 35+ Rentals in Lake Keystone

Ridgeland

Set within a welcoming community, Ridgeland provides a charming atmosphere combined with convenient proximity to Odessa’s amenities. It’s perfect for travelers wanting a comfortable stay in a quiet neighborhood that still keeps them connected to the area's vibrant culture.

View 45+ Rentals in Ridgeland

Cheval West

Located just outside Odessa, Cheval West features upscale neighborhoods and lush landscapes, ideal for visitors looking for elegant vacation rentals in a distinguished area. Here, you can enjoy a blend of privacy and accessibility to the region’s popular sights.

View 68+ Rentals in Cheval West

Cumberland Manors

Situated within a well-established community, Cumberland Manors offers spacious properties and a peaceful environment, making it a desirable spot for those wanting a relaxing stay close to Odessa’s natural beauty and local conveniences.

View 225+ Rentals in Cumberland Manors

Swan View Townhomes

This neighborhood provides modern townhomes with stylish amenities, perfect for travelers seeking comfort and functionality during their time here. Its convenient location makes it easy to explore Odessa’s attractions and enjoy the region’s outdoor lifestyle.

View 40+ Rentals in Swan View Townhomes

Best Times to Visit Odessa

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here ensures you can enjoy the region's climate and local events at their best, making your stay in Odessa, Florida, USA, truly memorable and relaxing.

Peak Season Highlights

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Spring (March to May)

Experience the region during spring when the weather is warm and pleasant, perfect for enjoying outdoor activities and exploring the area with comfortable daytime temperatures.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
summer
Summer (June to August)

Visit here in summer when the area comes alive with vibrant energy, ideal for beach outings and outdoor events amidst hot and humid conditions.

Average Temperature Daytime: 85°F to 90°F - Nighttime: 70°F to 75°F

Off-Season Highlights

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Fall (September to November)

During fall, the region offers cooler weather and fewer crowds, making it a great time to enjoy peaceful stays and local events without the peak season hustle.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
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Winter (December to February)

In winter, the area experiences mild temperatures that appeal to visitors seeking a quieter retreat away from the busy tourist months, ideal for relaxing in cozy accommodations.

Average Temperature Daytime: 60°F to 70°F - Nighttime: 40°F to 50°F

Weekly Weather Forecast for Odessa

How to Book Your Odessa 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 Odessa

More Top-Rated Vacation Rentals in Odessa 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 vacation rentals in the area, perfect for relaxing after a day exploring nearby attractions.
  • Take advantage of spacious private patios or decks to enjoy meals or unwind while soaking up the sunny Florida weather.
  • Many properties feature lush, well-maintained gardens or landscaped yards to enhance your outdoor experience.
  • Utilize outdoor grilling areas or BBQ facilities to host memorable cookouts with family and friends.
  • Benefit from access to tennis courts or pickleball courts often found in community settings within the region.
  • Relax on furnished balconies or verandas that provide scenic views of the surrounding landscape or nearby lakes.
  • Some vacation rentals include outdoor fire pits, ideal for cozy evenings under the stars during your stay here.

Top Attractions Around Odessa

What attractions are nearby?

Within this destination, you can enjoy a variety of outdoor activities and explore local parks, offering plenty of opportunities for relaxation and recreation during your stay.

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Family Activities

  • Suncoast Watersports: Experience a fun-filled day with water activities like paddleboarding and kayaking on nearby lakes, perfect for family adventure in the area.
  • Odessa Community Park: Enjoy outdoor picnics, playgrounds, and walking trails in this family-friendly park situated close to your vacation rental.
  • Local Wildlife Reserves: Discover native wildlife and nature walks, providing educational and entertaining experiences for children and adults alike here in the region.
  • Family-Friendly Dining: Explore a variety of casual restaurants and cafes that cater to families, offering delicious meals just minutes from your stay in Odessa.
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Adult Activities

  • Golfing at the Odessa Golf and Country Club: Enjoy a relaxing day on scenic courses that cater to all skill levels, offering both challenges and breathtaking views.
  • Exploring local parks and nature preserves: Discover the area's natural beauty through peaceful walks and wildlife observation in nearby parks and preserved lands.
  • Shopping and dining in the region's retail centers: Experience a variety of shopping options and taste local cuisine at popular restaurants nestled within this vibrant area.
  • Visiting cultural and community events: Immerse yourself in the local culture by attending seasonal festivals, markets, and live performances held throughout the year here.

Other Places to Stay in Odessa, FL

Lake Rogers Park
Lake Rogers Park Vacation Rentals
Brooker Creek Headwaters Nature Preserve
Brooker Creek Headwaters Nature Preserve Vacation Rentals
Crescent Lake
Crescent Lake Vacation Rentals
Lake Fern
Lake Fern Vacation Rentals
Ridgeland
Ridgeland Vacation Rentals
Swan View Townhomes
Swan View Townhomes Vacation Rentals
Silver Dollar Golf Club
Silver Dollar Golf Club Vacation Rentals
Lake Keystone
Lake Keystone Vacation Rentals
Keystone Lake
Keystone Lake Vacation Rentals
Keystone
Keystone Vacation Rentals
The Eagles Golf Club
The Eagles Golf Club Vacation Rentals
More Places to Stay Near Odessa

Odessa Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Outdoor Adventures: Take advantage of the region’s beautiful natural surroundings by exploring nearby parks and outdoor spaces to fully enjoy the scenic beauty of this Florida destination.
  • Discover Local Dining Options: Make sure to sample the area’s popular eateries, which showcase authentic flavors that highlight the region’s culinary charm during your stay.
  • Explore Nearby Attractions: Spend time visiting local points of interest that capture the essence of this destination, ensuring a memorable experience in the area.
  • Choose the Right Vacation Rental: Select a comfortable, well-located property that provides easy access to key sites, helping you make the most of your visit here.

Transportation Options

  • Odessa Trolley Service: This convenient option offers local transportation around the region, making it easy for you to explore nearby attractions without hassle.
  • Rental Cars: Opting for a rental car provides the flexibility to discover the area at your own pace, with numerous agencies available close to vacation rentals here.
  • Public Transit Buses: Local bus services connect key points across the destination, offering an affordable way to navigate the region comfortably.
  • Taxi and Ride-Sharing Services: Reliable taxi and ride-sharing options are readily accessible, providing quick and effortless transportation directly from your vacation rental here.

Local Customs Options

  • Southern Hospitality: You will notice a warm and welcoming attitude from locals that embodies the regional charm of Odessa, Florida, making your stay more inviting.
  • Fresh Seafood Celebrations: Participating in local seafood festivals and dining traditions gives you a taste of coastal culture unique to this destination.
  • Community Events: Engaging with neighborhood gatherings and farmers' markets provides a glimpse into the area’s close-knit and friendly atmosphere.
  • Respect for Nature: Observing local customs that emphasize environmental preservation encourages you to enjoy the region’s natural beauty responsibly.

Frequently Asked Questions About Odessa?

1. What are the top vacation rentals in Odessa?

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

2. How many vacation rentals have private pools in Odessa?

There are 1 vacation rentals with private pools near Odessa. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Odessa are best for families?

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

4. How many Rentbyowner vacation rentals are available in Odessa?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 65 in the Odessa 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 Odessa. 

5. What is the cancellation policy for vacation rentals in Odessa, Florida?

Cancellation policies vary by listing, so it’s important to review the specific terms provided by the owner before booking. Many rentals offer flexible options, but some may have stricter rules, especially during peak seasons or special events.

6. How do I know if a vacation rental in Odessa, Florida, is available for my travel dates?

Availability is shown in real-time on the listing page. To ensure your dates are open, use the booking calendar and contact the property owner if you have any questions about availability or potential scheduling conflicts.

7. Are there any house rules or restrictions I should be aware of when staying in a vacation rental here?

Each property has its own set of house rules and restrictions that are outlined in the listing. It’s recommended to read these carefully before booking, as they can include policies on pets, smoking, noise levels, and maximum occupancy.

8. What amenities can I expect in a vacation rental in this region?

Amenities vary by property but often include essentials such as Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces. Be sure to check the listing details for the specific amenities available at your chosen rental.

9. How do I contact the owner or manager if I have questions about my stay?

Contact information is provided in the listing, allowing you to communicate directly with the owner or property manager. It’s advisable to reach out prior to booking to clarify any concerns or special requests.