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

Osteen Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Osteen holiday 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
6.4 out of 10, (10 reviews)
"My family and I really enjoyed our stay. The room was spacious and accommodating at a very forgiving rate. The view was gorgeous and the beach was close by. We look forward to vacationing here again."
United States
Darla
The price is HK$487
HK$619 total
includes taxes & fees
24 Aug - 25 Aug
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
The price is HK$600
HK$1,199 total
includes taxes & fees
7 Aug - 8 Aug
Bella Breeze
Smart TV

3. 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
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
Exterior

4. 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
The price is HK$565
HK$1,159 total
includes taxes & fees
7 Aug - 8 Aug
The Jazz Loft
Interior

5. Totally 80's

Totally 80's
3.0 star property
Sanford
8.6 out of 10, Excellent, (11 reviews)
"Super cute property and fantastic hosts!!"
United States
Angi
The price is HK$529
HK$1,120 total
includes taxes & fees
7 Aug - 8 Aug
Totally 80's
Living area

6. The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is HK$600
HK$1,787 total
includes taxes & fees
9 Aug - 10 Aug
The Blue Aztec
Living area

7. Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
The price is HK$600
HK$1,199 total
includes taxes & fees
10 Aug - 11 Aug
Boho Nights
2 bedrooms, desk, free WiFi

8. 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
The price is HK$988
HK$1,766 total
includes taxes & fees
10 Aug - 11 Aug
The Front Porch
1 bedroom, iron/ironing board, WiFi, bed sheets

9. Serenity @ Court

Serenity @ Court
Sanford
9.8 out of 10, Exceptional, (16 reviews)
"The stay was very pleasurable. We plan to stay here again soon."
United States
William W.
The price is HK$941
HK$1,681 total
includes taxes & fees
5 Sept - 6 Sept
Serenity @ Court
Coffee/tea maker, fridge, microwave, paper towels

10. 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.
The price is HK$741
HK$987 total
includes taxes & fees
7 Aug - 8 Aug
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Exterior

11. 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.
The price is HK$635
HK$1,092 total
includes taxes & fees
17 Aug - 18 Aug
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Terrace/patio

12. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Perfect location within walking distance of all the fun yet nice and quiet. Place was squeaky clean. Will stay again"
United States
Min O.
The price is HK$667
HK$1,374 total
includes taxes & fees
10 Aug - 11 Aug
The Blue Aztec
1 bedroom, iron/ironing board, free WiFi, 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
The price is HK$776
HK$1,295 total
includes taxes & fees
31 Aug - 1 Sept
Mira Bella North - 1BR Tiny House in Lake Helen
Outdoor pool

14. 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, (63 reviews)
"Everything was great as usual!!"
United States
Christine B.
The price is HK$882
HK$2,102 total
includes taxes & fees
16 Aug - 17 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
3 bedrooms, desk, iron/ironing board, WiFi

15. 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.
The price is HK$918
HK$2,894 total
includes taxes & fees
11 Aug - 12 Aug
Tranquil 3-bedroom house in Sanford with AC, WiFi
Dining

16. 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.
The price is HK$953
HK$1,695 total
includes taxes & fees
16 Aug - 17 Aug
River City Retreat
Exterior

17. 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, (27 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.
The price is HK$1,129
HK$3,124 total
includes taxes & fees
9 Aug - 10 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Smart TV, fireplace, video games

18. Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits

Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
Lake Mary
10.0 out of 10, Exceptional, (20 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is HK$706
HK$1,881 total
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal! Crystal Springs Adventure Awaits
Interior

19. 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, (8 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.
The price is HK$776
HK$1,295 total
includes taxes & fees
10 Aug - 11 Aug
Mira Bella South - 1BR Tiny Home in Lake Helen
Exterior detail

20. Pet Friendly!✰ Charming home with big patio!

Pet Friendly!✰ Charming home with big patio!
Oviedo
9.8 out of 10, Exceptional, (24 reviews)
"Host was very helpful. It’s a nice place to stay. Very comfortable."
United States
Sandranel B.
The price is HK$902
HK$2,742 total
includes taxes & fees
10 Aug - 11 Aug
Pet Friendly!✰ Charming home with big patio!
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

Hilton Orlando/Altamonte Springs

Hilton Orlando/Altamonte Springs

10/10 Excellent
"This hotel was so reasonably priced for such a property. The staff is first-rate; everyone was so kind, helpful, friendly and genuine. My room was spacious, the bed was very comfortable and the air conditioning was powerful (very important to me). The hotel also has a great bar/restaurant with a varied menu with more than your standard fare. Breakfast was fantastic (but not free)."
Tamara 4-night trip
Posted less than an hour ago
Hilton Orlando/Altamonte Springs

Find out more about Osteen

Search for holiday rentals in Osteen on Expedia! You can easily find your home rentals, villas, holiday apartments in Osteen using one of the methods below:

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Look no further and take a look at our great range of rental properties in Osteen!

Frequently asked questions

Can I find holiday rentals in Osteen?

Yes, there are holiday rentals in Osteen close to Pell's Citrus & Nursery, or you can select a more secluded option if you're looking for a relaxing stay.

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

Pirates Cove Resort Studios: This holiday home rental outside of Osteen 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 holiday rentals are there in Osteen?

Expedia has 3 holiday rentals for your stay in Osteen.

What’s there to see and do in Osteen?

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

What’s a holiday rental in Osteen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osteen. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.