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

Holiday Rentals in Osteen

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Our top choices for Osteen holiday rentals

1. 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
The price is €143
includes taxes & fees
16 Aug - 17 Aug
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

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 €133
includes taxes & fees
15 Aug - 16 Aug
Bella Breeze

3. 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 €320
includes taxes & fees
16 Aug - 17 Aug
Tranquil 3-bedroom house in Sanford with AC, WiFi

4. 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 €191
includes taxes & fees
10 Sept - 11 Sept
Serenity @ Court

5. 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 €156
includes taxes & fees
16 Aug - 17 Aug
The Blue Aztec

6. 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
The price is €198
includes taxes & fees
16 Aug - 17 Aug
The Blue Aztec

7. 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 €195
includes taxes & fees
16 Aug - 17 Aug
The Front Porch

8. 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 €120
includes taxes & fees
16 Aug - 17 Aug
Boho Nights

9. 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 €128
includes taxes & fees
17 Aug - 18 Aug
The Jazz Loft

10. 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 €124
includes taxes & fees
7 Sept - 8 Sept
Totally 80's

11. 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.
The price is €151
includes taxes & fees
13 Sept - 14 Sept
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

12. 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 €384
includes taxes & fees
16 Aug - 17 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

13. 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 €188
includes taxes & fees
21 Aug - 22 Aug
River City Retreat

14. 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 €123
includes taxes & fees
8 Sept - 9 Sept
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

15. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Very comfortable and clean home! "
United States
Stacy B.
The price is €273
includes taxes & fees
17 Aug - 18 Aug
Home Sweet Home

16. Bella Breeze

Bella Breeze
Downtown Sanford
8.4 out of 10, Very good, (6 reviews)
"Enjoyable stay. "
United States
Carolyn R.
The price is €156
includes taxes & fees
14 Sept - 15 Sept
Bella Breeze

17. 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 €125
includes taxes & fees
17 Aug - 18 Aug
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

18. 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.
The price is €147
includes taxes & fees
16 Aug - 17 Aug
Mira Bella South - 1BR Tiny Home in Lake Helen

19. 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.
The price is €211
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal!

20. 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 €237
includes taxes & fees
16 Aug - 17 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone
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

Find out more about Osteen

Everything you need to know about Osteen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osteen holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osteen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osteen holiday rentals we have selected for you start as low as €68 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen holiday 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 holiday.

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. 

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 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 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.