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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Osteen vacation rentals

Smart TV

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 AED 347
AED 588 total
includes taxes & fees
16 Aug - 17 Aug
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood
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 AED 281
AED 562 total
includes taxes & fees
14 Aug - 15 Aug
Bella Breeze
3 bedrooms, desk, iron/ironing board, WiFi

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 AED 430
AED 1,355 total
includes taxes & fees
16 Aug - 17 Aug
Tranquil 3-bedroom house in Sanford with AC, WiFi
1 bedroom, iron/ironing board, WiFi, bed sheets

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 AED 441
AED 787 total
includes taxes & fees
7 Sep - 8 Sep
Serenity @ Court
Terrace/patio

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 Blue Aztec
Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

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 AED 268
AED 823 total
includes taxes & fees
16 Aug - 17 Aug
The Blue Aztec
2 bedrooms, desk, WiFi (free)

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 AED 456
AED 819 total
includes taxes & fees
23 Aug - 24 Aug
The Front Porch
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

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 AED 239
AED 514 total
includes taxes & fees
18 Aug - 19 Aug
Boho Nights
Exterior

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 AED 258
AED 536 total
includes taxes & fees
17 Aug - 18 Aug
The Jazz Loft
Interior

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 AED 239
AED 515 total
includes taxes & fees
21 Aug - 22 Aug
Totally 80's
Interior

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 AED 360
AED 621 total
includes taxes & fees
4 Sep - 5 Sep
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Exterior

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 AED 645
AED 1,626 total
includes taxes & fees
16 Aug - 17 Aug
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!
Dining

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 AED 446
AED 794 total
includes taxes & fees
19 Aug - 20 Aug
River City Retreat
Coffee/tea maker, fridge, microwave, paper towels

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 AED 347
AED 462 total
includes taxes & fees
14 Aug - 15 Aug
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex
Coffee/tea maker, fridge, microwave, oven

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 AED 248
AED 1,143 total
includes taxes & fees
17 Aug - 18 Aug
Home Sweet Home
Interior

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 AED 312
AED 644 total
includes taxes & fees
14 Aug - 15 Aug
Bella Breeze
Exterior

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 AED 298
AED 511 total
includes taxes & fees
17 Aug - 18 Aug
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Interior

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 AED 364
AED 607 total
includes taxes & fees
16 Aug - 17 Aug
Mira Bella South - 1BR Tiny Home in Lake Helen
Smart TV, fireplace, video games

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 AED 327
AED 855 total
includes taxes & fees
17 Aug - 18 Aug
Early Check In Lake Mary Last-Minute Deal!
Outdoor pool

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 AED 413
AED 984 total
includes taxes & fees
15 Aug - 16 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

Nautilus Inn

Nautilus Inn

10/10 Excellent
"Everything was exactly, I will recommend this hotel."
Halina 7-night trip
Posted 2 hours 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?

Pirates Cove Resort Studios: Visitors like this Osteen vacation home rental. It 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 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 Ashby Park and Lake Butler Chain 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.