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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Osteen vacation rentals

Interior

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (21 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 AED 281
AED 562 total
includes taxes & fees
29 Sep - 30 Sep
Bella Breeze
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

2. 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 AED 250
AED 527 total
includes taxes & fees
30 Sep - 1 Oct
Boho Nights
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)
"Great stay! "
United States
Ash L.
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 AED 238
AED 513 total
includes taxes & fees
6 Oct - 7 Oct
The Jazz Loft
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

5. 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 AED 250
AED 802 total
includes taxes & fees
30 Sep - 1 Oct
The Blue Aztec
Property grounds

6. A Backyard Retreat Worth Finding • Close to Downtown Sanford

A Backyard Retreat Worth Finding • Close to Downtown Sanford
Sanford
10.0 out of 10, Exceptional, (8 reviews)
"Cute, clean , cozy and convenient. We loved our stay at The Sanctuary Den!!!!!"
United States
james L.
The price is AED 264
AED 719 total
includes taxes & fees
28 Sep - 29 Sep
A Backyard Retreat Worth Finding • Close to Downtown Sanford
Interior

7. 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, (20 reviews)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
The price is AED 360
AED 621 total
includes taxes & fees
28 Sep - 29 Sep
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Interior

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 AED 393
AED 514 total
includes taxes & fees
28 Sep - 29 Sep
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Outdoor pool

9. 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, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is AED 314
AED 837 total
includes taxes & fees
28 Sep - 29 Sep
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
2 bedrooms, desk, WiFi (free)

10. 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 AED 463
AED 827 total
includes taxes & fees
28 Sep - 29 Sep
The Front Porch
Coffee/tea maker, fridge, microwave, oven

11. 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.
The price is AED 248
AED 1,088 total
includes taxes & fees
29 Sep - 30 Sep
Home Sweet Home
3 bedrooms, desk, iron/ironing board, WiFi

12. 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 AED 430
AED 1,275 total
includes taxes & fees
28 Sep - 29 Sep
Tranquil 3-bedroom house in Sanford with AC, WiFi
Exterior

13. 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, (43 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is AED 298
AED 511 total
includes taxes & fees
5 Oct - 6 Oct
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Smart TV, fireplace, video games

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is AED 281
AED 800 total
includes taxes & fees
28 Sep - 29 Sep
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
1 bedroom, iron/ironing board, WiFi (free), bed sheets

15. 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, (10 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 AED 382
AED 648 total
includes taxes & fees
28 Sep - 29 Sep
Mira Bella North - 1BR Tiny House in Lake Helen
Dining

16. River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (21 reviews)
"Worked great for our needs!"
United States
Kelley H.
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, (29 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 AED 496
AED 1,349 total
includes taxes & fees
28 Sep - 29 Sep
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Marina

18. NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry

NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
Orlando
9.2 out of 10, Wonderful, (13 reviews)
"The studio is super cute with nice outdoor space. Close to UCF campus, restaurants, and shopping."
United States
Michael
The price is AED 272
AED 618 total
includes taxes & fees
28 Sep - 29 Sep
NEW Designed Apt 2023 NrUCF PETSOk PrivateEntry
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, (11 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 AED 382
AED 648 total
includes taxes & fees
30 Sep - 1 Oct
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

Nautilus Inn

Nautilus Inn

10/10 Excellent
"Room was clean, love having the kitchen for meals. We had a problem with the toilet upon arrival and they had it fixed very quickly. easy access to the beach and a great view. Staff is very friendly and helpful."
Dawn 2-night trip
Posted 1 hour ago
Nautilus Inn

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?

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!: Visitors like this Osteen vacation home rental. It is located by the ocean and has a garden, a barbecue grill, 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 you can cook with friends or family.

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 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 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.