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
9.8 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 CA $102
CA $210 total
includes taxes & fees
Oct 13 - Oct 14
Bella Breeze

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 CA $115
CA $225 total
includes taxes & fees
Oct 13 - Oct 14
Boho Nights

3. 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 $212
CA $357 total
includes taxes & fees
Oct 12 - Oct 13
The Front Porch

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 CA $90
CA $196 total
includes taxes & fees
Oct 11 - Oct 12
The Jazz Loft

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 CA $103
CA $318 total
includes taxes & fees
Oct 11 - Oct 12
The Blue Aztec

6. 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 $109
CA $324 total
includes taxes & fees
Oct 12 - Oct 13
The Mellow Yellow

7. 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 CA $226
CA $254 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Vacation Club Daytona Seabreeze Daytona Beach

8. Howard Johnson by Wyndham Oceanfront Daytona Beach

Howard Johnson by Wyndham Oceanfront Daytona Beach
2.0 star property
South Peninsula Historic District
7.6 out of 10, Good, (37 reviews)
"Amazing place"
United States
Kristin
The price is CA $76
CA $98 total
includes taxes & fees
Oct 22 - Oct 23
Howard Johnson by Wyndham Oceanfront Daytona Beach

9. Oceania II

Oceania II
4.0 star property
Central Beach
10.0 out of 10, Exceptional, (1 review)
The price is CA $405
CA $885 total
includes taxes & fees
Oct 11 - Oct 12
Oceania II

10. 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, (137 reviews)
"It was super clean and quiet too. Everyone was super friendly!"
United States
Jessica
The price is CA $117
CA $179 total
includes taxes & fees
Oct 23 - Oct 24
Fantasy Island Resort, Daytona Beach Shores

11. Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
9.2 out of 10, Wonderful, (28 reviews)
"Clean, quiet and quite spacious! Great ocean views!"
United States
Diane
The price is CA $154
CA $174 total
includes taxes & fees
Oct 21 - Oct 22
Catalina Beach Club

12. Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort
3.5 star property
Daytona Beach Shores
8.4 out of 10, Very good, (75 reviews)
"We loved the location right on the beach and the pool!"
United States
Paige
The price is CA $115
CA $129 total
includes taxes & fees
Nov 8 - Nov 9
Tropical Suites at Sunglow Resort

13. Shoreline Suites & Cabana Cottages

Shoreline Suites & Cabana Cottages
2.0 star property
Daytona Beach Shores
8.8 out of 10, Excellent, (390 reviews)
"The cottages are really cute and right on the beach."
United States
Laurie
The price is CA $167
CA $187 total
includes taxes & fees
Oct 11 - Oct 12
Shoreline Suites & Cabana Cottages

14. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is CA $104
CA $223 total
includes taxes & fees
Oct 21 - Oct 22
Cozy Modern Studio

15. Steps to Atlantic Ocean & Dining! Couples Retreat

Steps to Atlantic Ocean & Dining! Couples Retreat
3.0 star property
Coronado Beach
The price is CA $110
CA $290 total
includes taxes & fees
Oct 22 - Oct 23
Steps to Atlantic Ocean & Dining! Couples Retreat

16. Oceanfront Penthouse Pool Hot Tub Beach Access

Oceanfront Penthouse Pool Hot Tub Beach Access
2.0 star property
Daytona Beach Shores
10.0 out of 10, Exceptional, (2 reviews)
"The stay was so great I wish we could have stayed longer. I will be back. "
United States
Danielle
The price is CA $305
CA $863 total
includes taxes & fees
Nov 4 - Nov 5
Oceanfront Penthouse Pool Hot Tub Beach Access

17. Beach Front Studios in Daytona Beach

Beach Front Studios in Daytona Beach
3.0 star property
Daytona Beach
7.6 out of 10, Good, (178 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 $113
CA $225 total
includes taxes & fees
Oct 19 - Oct 20
Beach Front Studios in Daytona Beach

18. Beautiful Beachfront Resort Condo

Beautiful Beachfront Resort Condo
3.0 star property
Daytona Beach
9.0 out of 10, Wonderful, (19 reviews)
"Amazing location and cute little condo. Checking in was a little confusing with access codes. The views are incredible and the fireworks that could be seen from the balcony on Saturday nights were a bonus! Would stay here again."
United States
Kathleen
The price is CA $160
CA $341 total
includes taxes & fees
Oct 31 - Nov 1
Beautiful Beachfront Resort Condo

19. Oceania III

Oceania III
3.0 star property
Central Beach
9.8 out of 10, Exceptional, (10 reviews)
"Great location, close to everything, but not too close."
United States
Gregory
The price is CA $538
CA $1,034 total
includes taxes & fees
Oct 23 - Oct 24
Oceania III

20. 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 $90
CA $199 total
includes taxes & fees
Oct 12 - Oct 13
Pirates Cove Resort Studios
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?

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.