A sunset over a calm lake with islands and a bridge.

Osteen Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Osteen vacation rentals

27-inch flat-screen TV with cable channels, TV

1. Howard Johnson by Wyndham Oceanfront Daytona Beach

Howard Johnson by Wyndham Oceanfront Daytona Beach
2.0 star property
South Peninsula Historic District
6.8 out of 10, (12 reviews)
"Hi so I don’t have alot of complaints I paid 263 for 2 nights which was a good deal I was not aware there in the middle of a remodel there was no easy entrance to the beach you had to walk around to the main entrance the hot tub was down the pool was clean and nice not a bad stay you pay for what you get for staff was kind"
United States
Katie
$70 nightly
The price is $79
Sep 7 - Sep 8
Total with taxes and fees
Howard Johnson by Wyndham Oceanfront Daytona Beach
Interior

2. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (20 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
$145 nightly
The price is $162
Aug 22 - Aug 23
Total with taxes and fees
Bella Breeze
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

3. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$143 nightly
The price is $160
Aug 31 - Sep 1
Total with taxes and fees
Boho Nights
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

4. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (14 reviews)
"Great location! Great Dining! "
United States
Lisa
$213 nightly
The price is $230
Aug 19 - Aug 20
Total with taxes and fees
The Blue Aztec
Exterior

5. The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Great overnight stay. Really cute loft. Would definitely stay again."
United States
Tiffany
$137 nightly
The price is $153
Aug 19 - Aug 20
Total with taxes and fees
The Jazz Loft
Smart TV

6. A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Deltona
9.6 out of 10, Exceptional, (23 reviews)
"Host was extremely attentive and available whenever we reached out. She was flexible with our arrival as well. The property was clean, cozy and perfect for our needs. "
United States
Kimberly
$145 nightly
The price is $160
Aug 19 - Aug 20
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Terrace/patio

7. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (15 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
$158 nightly
The price is $167
Aug 19 - Aug 20
Total with taxes and fees
The Blue Aztec
Coffee/tea maker, fridge, microwave, oven

8. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"The house was perfect for our three night stay. The location was a short distance to all our activities. It was super clean and had very nice updates. The area was quiet and the house very comfortable. If we are in the area again, we’ll definitely stay there again!"
United States
Janice M.
$283 nightly
The price is $312
Aug 19 - Aug 20
Total with taxes and fees
Home Sweet Home
Exterior

9. The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Lake Helen
9.8 out of 10, Exceptional, (42 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
$126 nightly
The price is $139
Aug 19 - Aug 20
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Interior

10. Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Geneva
9.4 out of 10, Exceptional, (19 reviews)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
$143 nightly
The price is $158
Aug 22 - Aug 23
Total with taxes and fees
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Coffee/tea maker, fridge, microwave, paper towels

11. Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Sanford
10.0 out of 10, Exceptional, (8 reviews)
"Perfect spot for a quick night after your flight into Sanford. Close to the airport, clean accommodations in a quiet neighborhood. Couldn’t ask for more!"
United States
Julia F.
$152 nightly
The price is $168
Aug 22 - Aug 23
Total with taxes and fees
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
2 bedrooms, desk, WiFi (free)

12. The Front Porch

The Front Porch
3.0 star property
Downtown Sanford
9.2 out of 10, Wonderful, (5 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
$202 nightly
The price is $227
Aug 19 - Aug 20
Total with taxes and fees
The Front Porch
1 bedroom, iron/ironing board, WiFi (free), bed sheets

13. Mira Bella North - 1BR Tiny House in Lake Helen

Mira Bella North - 1BR Tiny House in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (8 reviews)
"From the start of our stay until the end, our host was amazing. The property is beautiful. You will love this property!"
United States
Angel
$149 nightly
The price is $165
Aug 19 - Aug 20
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen
3 bedrooms, desk, iron/ironing board, WiFi

14. Tranquil 3-bedroom house in Sanford with AC, WiFi

Tranquil 3-bedroom house in Sanford with AC, WiFi
Sanford
9.6 out of 10, Exceptional, (28 reviews)
"Beautiful home! My friends and I had such an amazing time and I loved the dog bed & bowls for my dog Venus who stayed with us"
United States
Janelle G.
$334 nightly
The price is $369
Aug 19 - Aug 20
Total with taxes and fees
Tranquil 3-bedroom house in Sanford with AC, WiFi
Smart TV, fireplace, video games

15. Early Check In Lake Mary Last-Minute Deal!

Early Check In Lake Mary Last-Minute Deal!
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$214 nightly
The price is $237
Aug 19 - Aug 20
Total with taxes and fees
Early Check In Lake Mary Last-Minute Deal!
Outdoor pool

16. Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (64 reviews)
"Everything was great as usual!!"
United States
Christine B.
$244 nightly
The price is $269
Aug 19 - Aug 20
Total with taxes and fees
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Interior

17. Bella Breeze

Bella Breeze
Downtown Sanford
8.4 out of 10, Very Good, (6 reviews)
"Enjoyable stay. "
United States
Carolyn R.
$166 nightly
The price is $176
Aug 22 - Aug 23
Total with taxes and fees
Bella Breeze
Dining

18. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (20 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
$193 nightly
The price is $213
Aug 25 - Aug 26
Total with taxes and fees
River City Retreat
Exterior

19. Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Sanford
10.0 out of 10, Exceptional, (28 reviews)
"We absolutely loved this house! So cute and ample space. The outdoor space was so nice to grill and hangout!"
United States
Danielle C.
$357 nightly
The price is $395
Aug 20 - Aug 21
Total with taxes and fees
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Interior

20. Mira Bella South - 1BR Tiny Home in Lake Helen

Mira Bella South - 1BR Tiny Home in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (9 reviews)
"I enjoyed everything about Mira Bella. The accommodations were great and Dara was very responsive. Would definitely stay again in the future."
United States
susan b.
$149 nightly
The price is $165
Aug 19 - Aug 20
Total with taxes and fees
Mira Bella South - 1BR Tiny Home in Lake Helen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osteen Hotel Reviews

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Holiday Inn Express & Suites Sanford- Lake Mary by IHG

10/10 Excellent
"Very clean and updated room, comfy beds, quality soap and nice, strong shower. Decent fridge and microwave, hair dryer and clean, white linens. Comfortable lobby with several televisions. Spacious dining area for delicious hot breakfast with several options and free parking! Close to highway, shopping and dining options. This is our go-to hotel when in the Sanford/Lake Mary area!"
Pierre 2-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Sanford- Lake Mary by IHG

Find out more about Osteen

Everything you need to know about Osteen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osteen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osteen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osteen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osteen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $78 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osteen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osteen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osteen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Osteen?

Yes, we have vacation rentals in Osteen close to Pell's Citrus & Nursery, or you can choose a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Osteen has to offer?

Pirates Cove Resort Studios: Visitors like this Osteen vacation home rental. It is on the beach and equipped with air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave, and a coffee maker.

How many vacation rentals are there in Osteen?

Expedia has 3 vacation rentals for your stay in Osteen.

What’s there to see and do in Osteen?

Lake Jesup and Lake Butler Chain are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Pell's Citrus & Nursery. Lake Monroe Conservation Area and Lake Jesup Conservation Area are other places to visit while you're in town.

What’s a vacation rental in Osteen like?

Vacation rentals are private properties you can stay in for several days or longer in Osteen. Vacation rentals provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.