Osteen Holiday Rentals

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Check prices for these dates

Our top choices for Osteen holiday rentals

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (23 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 NZ$261
includes taxes & fees
11 Nov - 12 Nov
Bella Breeze

2. 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 NZ$282
includes taxes & fees
6 Nov - 7 Nov
The Jazz Loft

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 place to stay near the airport "
United States
Rodney
The price is NZ$624
includes taxes & fees
8 Nov - 9 Nov
Tranquil 3-bedroom house in Sanford with AC, WiFi

4. 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 NZ$385
includes taxes & fees
8 Nov - 9 Nov
The Front Porch

5. 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 NZ$264
includes taxes & fees
8 Nov - 9 Nov
Boho Nights

6. The Blue Aztec

The Blue Aztec
Downtown Sanford
10.0 out of 10, Exceptional, (17 reviews)
"Everything was incredible and the owners were extremely helpful and accommodating! Would stay here again 100%!"
United States
Kael
The price is NZ$309
includes taxes & fees
8 Nov - 9 Nov
The Blue Aztec

7. Serenity @ Court

Serenity @ Court
Sanford
9.8 out of 10, Exceptional, (17 reviews)
"The stay was very pleasurable. We plan to stay here again soon."
United States
William W.
The price is NZ$338
includes taxes & fees
14 Nov - 15 Nov
Serenity @ Court

8. Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Sanford
9.8 out of 10, Exceptional, (9 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 NZ$221
includes taxes & fees
5 Nov - 6 Nov
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO

9. A Backyard Oasis Worth Finding • Close to Downtown Sanford

A Backyard Oasis Worth Finding • Close to Downtown Sanford
Sanford
10.0 out of 10, Exceptional, (9 reviews)
"Great cozy cute spot. Would stay again. Host was super responsive. Highly recommended."
United States
Blake
The price is NZ$349
includes taxes & fees
8 Nov - 9 Nov
A Backyard Oasis Worth Finding • Close to Downtown Sanford

10. Home Sweet Home

Home Sweet Home
Sanford
9.4 out of 10, Exceptional, (33 reviews)
"Second time to stay at property and it was ideal. Clean, comfortable and easy"
United States
Aimee B.
The price is NZ$549
includes taxes & fees
9 Nov - 10 Nov
Home Sweet Home

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, (44 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is NZ$234
includes taxes & fees
16 Nov - 17 Nov
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

12. 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, (12 reviews)
"Amazing place. Great fishing! Amenities were awesome. Close drive to town. We will return."
United States
John C.
The price is NZ$304
includes taxes & fees
9 Nov - 10 Nov
Mira Bella South - 1BR Tiny Home in Lake Helen

13. Cozy Countryside Studio Near Sanford - 1 BR, 1BA

Cozy Countryside Studio Near Sanford - 1 BR, 1BA
Sanford
9.8 out of 10, Exceptional, (6 reviews)
"Dana was amazing and was very accommodating. Our trip was relaxing and we would stay again. "
United States
Lisa B.
The price is NZ$356
includes taxes & fees
9 Nov - 10 Nov
Cozy Countryside Studio Near Sanford - 1 BR, 1BA

14. 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, (31 reviews)
"Really cute cottage with charming eclectic style. Stayed with two adults and four teens and everyone had plenty of space with comfortable sleeping. Would absolutely stay again!"
United States
Wendy K.
The price is NZ$780
includes taxes & fees
8 Nov - 9 Nov
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

15. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (69 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is NZ$458
includes taxes & fees
16 Nov - 17 Nov
Orlando Pool Days & Hammock Naps Book Your Escape NOW!

16. Howard Johnson by Wyndham Oceanfront Daytona Beach

Howard Johnson by Wyndham Oceanfront Daytona Beach
2.0 star property
South Peninsula Historic District
8.0 out of 10, Very good, (68 reviews)
"Best rooms in Daytona Beach for the money, it had everything you needed"
United States
Kevin
The price is NZ$134
includes taxes & fees
5 Nov - 6 Nov
Howard Johnson by Wyndham Oceanfront Daytona Beach

17. Hilton Vacation Club Daytona Seabreeze Daytona Beach

Hilton Vacation Club Daytona Seabreeze Daytona Beach
3.0 star property
Daytona Beach Shores
8.8 out of 10, Excellent, (22 reviews)
"We loved this place, great customer service, clean modern rooms and beautiful views from our balcony. It was quiet, relaxing and one of the best places we’ve stayed at near Daytona shores. "
United States
Kevin
The price is NZ$299
includes taxes & fees
8 Nov - 9 Nov
Hilton Vacation Club Daytona Seabreeze Daytona Beach

18. Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
9.4 out of 10, Exceptional, (39 reviews)
"Great stay with friendly staff. Plenty to do on property for the lazy days!"
United States
James
The price is NZ$238
includes taxes & fees
16 Nov - 17 Nov
Catalina Beach Club

19. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is NZ$434
includes taxes & fees
2 Dec - 3 Dec
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

20. Fantasy Island Resort, Daytona Beach Shores

Fantasy Island Resort, Daytona Beach Shores
4.0 star property
Rio Mar Beaches
8.6 out of 10, Excellent, (141 reviews)
"It was super clean and quiet too. Everyone was super friendly!"
United States
Jessica
The price is NZ$223
includes taxes & fees
2 Dec - 3 Dec
Fantasy Island Resort, Daytona Beach Shores
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.

Find holiday rentals that suit your style

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, 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 NZ$134 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?

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!: This holiday home rental outside of Osteen is located by the ocean, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.