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

Osteen Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Osteen vacation rentals

Interior

1. 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 ￥11,942
￥23,866 total
includes taxes & fees
Sep 9 - Sep 10
Bella Breeze
Standard Apartment | Living area

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 ￥11,942
￥23,866 total
includes taxes & fees
Sep 22 - Sep 23
Boho Nights
Standard Apartment | Living area

3. 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 ￥11,660
￥35,638 total
includes taxes & fees
Sep 28 - Sep 29
The Blue Aztec
Property grounds

4. 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.
A Backyard Retreat Worth Finding • Close to Downtown Sanford
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
The price is ￥11,239
￥23,078 total
includes taxes & fees
Sep 14 - Sep 15
The Jazz Loft
Terrace/patio

6. 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
The price is ￥13,496
￥27,818 total
includes taxes & fees
Sep 7 - Sep 8
The Blue Aztec
Terrace/patio

7. Boho Nights

Boho Nights
Downtown Sanford
10.0 out of 10, Exceptional, (14 reviews)
"Best stay in Downtown Sanford"
United States
John C.
The price is ￥13,496
￥27,818 total
includes taxes & fees
Sep 7 - Sep 8
Boho Nights
Exterior

8. 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 ￥12,861
￥22,110 total
includes taxes & fees
Sep 7 - Sep 8
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Room

9. 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 ￥18,577
￥58,120 total
includes taxes & fees
Sep 8 - Sep 9
Tranquil 3-bedroom house in Sanford with AC, WiFi
Room

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 ￥19,669
￥35,141 total
includes taxes & fees
Sep 9 - Sep 10
The Front Porch
Private kitchen

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 ￥10,677
￥48,424 total
includes taxes & fees
Sep 9 - Sep 10
Home Sweet Home
Interior

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, (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 ￥16,513
￥28,005 total
includes taxes & fees
Sep 8 - Sep 9
Mira Bella South - 1BR Tiny Home in Lake Helen
Bathroom

13. 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 ￥20,006
￥25,582 total
includes taxes & fees
Sep 6 - Sep 7
Modern Private Suite w/Dedicated Entrance-Minutes to Boombah Sports, SFB & MCO
Pool

14. 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)
"A great, cozy home that checked all of our boxes. We have stayed a few times with this host and find them consistently good. Very comfy and clean!! Already have them booked twice more!"
United States
Lisa M.
The price is ￥13,576
￥36,960 total
includes taxes & fees
Sep 8 - Sep 9
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Terrace/patio

15. The Front Porch

The Front Porch
Downtown Sanford
10.0 out of 10, Exceptional, (9 reviews)
"Nicely decorated great location"
United States
stephanie b.
The price is ￥22,229
￥40,457 total
includes taxes & fees
Sep 7 - Sep 8
The Front Porch
Living area

16. Labor Day Weekend! Orlando Last-Minute Deal! Book Today!

Labor Day Weekend! Orlando Last-Minute Deal! Book Today!
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 ￥12,147
￥35,200 total
includes taxes & fees
Sep 8 - Sep 9
Labor Day Weekend! Orlando Last-Minute Deal! Book Today!
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, (28 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.
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Room

18. 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, (9 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 ￥16,513
￥28,005 total
includes taxes & fees
Sep 7 - Sep 8
Mira Bella North - 1BR Tiny House in Lake Helen
Room

19. Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
Casselberry
9.8 out of 10, Exceptional, (55 reviews)
"The residence met all of our needs for an entertaining/relaxing stay."
United States
Kevin K.
The price is ￥20,371
￥39,582 total
includes taxes & fees
Sep 9 - Sep 10
Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osteen Hotel Reviews

Nautilus Inn

Nautilus Inn

10/10 Excellent
"We loved everything about our stay at Nautilus Inn! The room was spotless and had everything we could possibly need or want. The staff was very friendly and helpful. The price was very reasonable. The location was great. The beach view was outstanding. The patio and pool area was very nice. Everything in the hotel inside and out was well maintained and spotlessly clean. We were so impressed. We’re definitely going back!"
Laurie 2-night trip
Posted 4 hours ago
Nautilus Inn

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:

  • View our selection of featured holiday rentals in Osteen
  • Use the map to find apartments and other holiday homes in the Osteen neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osteen while they last

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

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?

Daytona Beach XI: You might want to consider this vacation home rental near Osteen, which is located near the beach and offers an arcade game room, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

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 Ashby Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Pell's Citrus & Nursery. Lake Butler Chain and Lake Monroe 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.