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

Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

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 CA $105
CA $210 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $95
CA $198 total
includes taxes & fees
Aug 26 - Aug 27
The Jazz Loft

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 CA $105
CA $314 total
includes taxes & fees
Aug 31 - Sep 1
The Blue Aztec

4. 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 CA $102
CA $207 total
includes taxes & fees
Sep 14 - Sep 15
Boho Nights

5. 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 CA $166
CA $301 total
includes taxes & fees
Sep 1 - Sep 2
The Front Porch

6. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is CA $96
CA $211 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Modern Studio

7. The Mellow Yellow

The Mellow Yellow
3.0 star property
Downtown Sanford
6.0 out of 10, (3 reviews)
"Owners had over booked this property, but proactively reached out and moved me to like property, BoHo Nights. Very nice place. Easy walk to downtown Sanford. Coffee options provided were appreciated."
United States
Gary
The price is CA $99
CA $307 total
includes taxes & fees
Aug 25 - Aug 26
The Mellow Yellow

8. Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
8.6 out of 10, Excellent, (14 reviews)
"Really enjoyed the price of a beach view. Nice place to stay. Would recommend this place for anyone going to Daytona Beach."
United States
John
The price is CA $143
CA $161 total
includes taxes & fees
Sep 7 - Sep 8
Catalina Beach Club

9. Pirates Cove Resort Studios

Pirates Cove Resort Studios
3.0 star property
Daytona Beach Shores
6.2 out of 10, (161 reviews)
"It was amazing. Awesome room."
United States
Rachel
The price is CA $107
CA $216 total
includes taxes & fees
Aug 25 - Aug 26
Pirates Cove Resort Studios

10. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is CA $168
CA $384 total
includes taxes & fees
Aug 25 - Aug 26
The Contemporary

11. Beach Front Studios in Daytona Beach

Beach Front Studios in Daytona Beach
3.0 star property
Daytona Beach
7.6 out of 10, Good, (176 reviews)
"I absolutely loved my stay in Daytona ! Easy access to the beach the pool and spa tub was everything 10/10 highly recommend "
United States
Jamillah
The price is CA $107
CA $216 total
includes taxes & fees
Aug 25 - Aug 26
Beach Front Studios in Daytona Beach

12. Fantasy Island Resort, Daytona Beach Shores

Fantasy Island Resort, Daytona Beach Shores
4.0 star property
Rio Mar Beaches
8.8 out of 10, Excellent, (133 reviews)
"It was super clean and quiet too. Everyone was super friendly!"
United States
Jessica
The price is CA $117
CA $178 total
includes taxes & fees
Sep 7 - Sep 8
Fantasy Island Resort, Daytona Beach Shores

13. Hawaiian Inn Studios

Hawaiian Inn Studios
2.5 star property
Daytona Beach Shores
5.2 out of 10, (21 reviews)
"Everything was ok. Just a few details that have to be fix like the stove, just one burner working, the balcony door handler. The rest was fine. Excellent ocean view."
United States
Braulio
The price is CA $107
CA $216 total
includes taxes & fees
Aug 25 - Aug 26
Hawaiian Inn Studios

14. Castaways Resort Studios

Castaways Resort Studios
3.0 star property
Daytona Beach Shores
6.0 out of 10, (117 reviews)
"Beach access was great. Room was clean"
United States
TAMMY
The price is CA $87
CA $192 total
includes taxes & fees
Aug 25 - Aug 26
Castaways Resort Studios

15. Shoreline Suites & Cabana Cottages

Shoreline Suites & Cabana Cottages
2.0 star property
Daytona Beach Shores
8.8 out of 10, Excellent, (389 reviews)
"The cottages are really cute and right on the beach."
United States
Laurie
The price is CA $145
CA $163 total
includes taxes & fees
Aug 31 - Sep 1
Shoreline Suites & Cabana Cottages

16. Daytona 2BR Getaway Parking Family & Pet-friendly

Daytona 2BR Getaway Parking Family & Pet-friendly
3.0 star property
Daytona Beach
The price is CA $207
CA $524 total
includes taxes & fees
Aug 31 - Sep 1
Daytona 2BR Getaway Parking Family & Pet-friendly

17. Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort
4.5 star property
Daytona Beach Shores
8.4 out of 10, Very good, (73 reviews)
"Clean and comfortable condo , directly on the beach with a couple beach chairs in closet for our use . Pool was very nice and some took advantage of late night swims . Plenty of soaps , towels , and even coffee . Only disadvantage was no extra pillows , sheets or blanket for sofa bed , so might want to plan ahead with management . Would stay again."
United States
Cheryl
The price is CA $92
CA $427 total
includes taxes & fees
Aug 31 - Sep 1
Tropical Suites at Sunglow Resort

18. Ocean Front Condo w Amazing Views Pool Hot Tub

Ocean Front Condo w Amazing Views Pool Hot Tub
2.0 star property
Daytona Beach Shores
The price is CA $194
CA $652 total
includes taxes & fees
Aug 25 - Aug 26
Ocean Front Condo w Amazing Views Pool Hot Tub

19. Sun, Sand & Smiles: Daytona Shores Family Condo!

Sun, Sand & Smiles: Daytona Shores Family Condo!
3.0 star property
Daytona Beach Shores
The price is CA $206
CA $564 total
includes taxes & fees
Aug 25 - Aug 26
Sun, Sand & Smiles: Daytona Shores Family Condo!

20. Oceania I

Oceania I
4.0 star property
Central Beach
8.0 out of 10, Very good, (4 reviews)
"Great oceanview"
United States
Kathleen
The price is CA $301
CA $713 total
includes taxes & fees
Aug 28 - Aug 29
Oceania I
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osteen. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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: Visitors like this Osteen vacation home rental. It 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 Jesup Conservation Area 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.