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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Osteen vacation rentals

A modern kitchen with a marble countertop, gold faucets, and a large window.

1. Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.8 out of 10, Exceptional, (23 reviews)
"The location was perfect, can walk to restaurants easily. Unit was very clean and nicely designed, would stay again"
United States
Sara
$145 nightly
The price is $162
Nov 3 - Nov 4
Total with taxes and fees
Bella Breeze
A backyard with a hammock, outdoor seating, and string lights.

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
$150 nightly
The price is $168
Nov 8 - Nov 9
Total with taxes and fees
The Jazz Loft
A modern living room with a grey sofa, two armchairs, a coffee table, and a small side table with a lamp. There is a brick fireplace, a kitchen area with a countertop and cabinets, and a large window with blinds.

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
$274 nightly
The price is $307
Nov 15 - Nov 16
Total with taxes and fees
The Front Porch
A compact kitchen with a built-in sink, a countertop, and a grey cabinet. There is a sofa with a cushion and a small table in the adjacent living area.

4. 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
$207 nightly
The price is $232
Nov 3 - Nov 4
Total with taxes and fees
The Mellow Yellow
A living room with a sofa, coffee table, and a dining area with chairs and a table.

5. Howard Johnson by Wyndham Oceanfront Daytona Beach

Howard Johnson by Wyndham Oceanfront Daytona Beach
2.0 star property
South Peninsula Historic District
8.0 out of 10, Very good, (64 reviews)
"Best rooms in Daytona Beach for the money, it had everything you needed"
United States
Kevin
$68 nightly
The price is $75
Nov 1 - Nov 2
Total with taxes and fees
Howard Johnson by Wyndham Oceanfront Daytona Beach
A beach with sun loungers and umbrellas, a sandy shore, and high-rise buildings in the background.

6. 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
$149 nightly
The price is $167
Nov 1 - Nov 2
Total with taxes and fees
Hilton Vacation Club Daytona Seabreeze Daytona Beach
A living room with a sofa, armchair, and a coffee table. There is a ceiling fan, a TV, and a window with curtains.

7. Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
9.4 out of 10, Exceptional, (37 reviews)
"Great stay with friendly staff. Plenty to do on property for the lazy days!"
United States
James
$106 nightly
The price is $119
Nov 8 - Nov 9
Total with taxes and fees
Catalina Beach Club
An aerial view of a coastal city with a beachfront, dense urban area, and a marina.

8. 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, (139 reviews)
"It was super clean and quiet too. Everyone was super friendly!"
United States
Jessica
$111 nightly
The price is $125
Nov 29 - Nov 30
Total with taxes and fees
Fantasy Island Resort, Daytona Beach Shores
A balcony with a view of the ocean, a white sofa, a wicker table, and striped chairs.

9. Ocean Beach Club

Ocean Beach Club
3.0 star property
Coronado Beach
9.8 out of 10, Exceptional, (44 reviews)
"Very nice clean updated apartment. Modern updated appliances. On the beach close to restaurant and shopping"
United States
james
$479 nightly
The price is $538
Nov 27 - Nov 28
Total with taxes and fees
Ocean Beach Club
A beach view with a wooden pier extending into the ocean, a clear sky, and a railing in the foreground.

10. Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort
3.5 star property
Daytona Beach Shores
8.4 out of 10, Very good, (78 reviews)
"We loved the location right on the beach and the pool!"
United States
Paige
$69 nightly
The price is $77
Nov 1 - Nov 2
Total with taxes and fees
Tropical Suites at Sunglow Resort
A modern kitchen with a wooden dining table, a built-in oven, and a large window providing natural light.

11. Oceania I

Oceania I
4.0 star property
Central Beach
8.4 out of 10, Very good, (5 reviews)
"Great oceanview"
United States
Kathleen
$541 nightly
The price is $598
Nov 1 - Nov 2
Total with taxes and fees
Oceania I
A compact bedroom with a bed, a desk, a TV, and a ceiling fan.

12. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
$157 nightly
The price is $176
Nov 9 - Nov 10
Total with taxes and fees
Cozy Modern Studio
A beachfront hotel with rows of wooden chairs and tables aligned along a central walkway, leading to the ocean.

13. Shoreline Suites & Cabana Cottages

Shoreline Suites & Cabana Cottages
2.0 star property
Daytona Beach Shores
8.8 out of 10, Excellent, (391 reviews)
"The cottages are really cute and right on the beach."
United States
Laurie
$105 nightly
The price is $118
Nov 1 - Nov 2
Total with taxes and fees
Shoreline Suites & Cabana Cottages
A balcony with a pool and beach view.

14. 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)
"Everything was great I’d stay again for sure"
United States
James
$147 nightly
The price is $157
Nov 1 - Nov 2
Total with taxes and fees
Beach Front Studios in Daytona Beach
A hotel room with a large bed, a sofa, a chair, and a balcony with a view of the beach.

15. The Coastal Current at Tropical Suites Sunglow Resort

The Coastal Current at Tropical Suites Sunglow Resort
2.0 star property
Daytona Beach Shores
$292 nightly
The price is $328
Nov 1 - Nov 2
Total with taxes and fees
The Coastal Current at Tropical Suites Sunglow Resort
A balcony with two Adirondack chairs and a small table, overlooking a beach with a clear sky.

16. 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
$250 nightly
The price is $281
Nov 1 - Nov 2
Total with taxes and fees
Beautiful Beachfront Resort Condo
A balcony with turquoise chairs overlooking a pool and a beach.

17. Castaways Resort Studios

Castaways Resort Studios
3.0 star property
Daytona Beach Shores
6.0 out of 10, (119 reviews)
"Beach access was great. Room was clean"
United States
TAMMY
$132 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Castaways Resort Studios
Private kitchen

18. Accessible Orlando Retreat With Jacuzzi and Shared Pool

Accessible Orlando Retreat With Jacuzzi and Shared Pool
2.0 star property
Goldenrod
$107 nightly
The price is $120
Oct 31 - Nov 1
Total with taxes and fees
Accessible Orlando Retreat With Jacuzzi and Shared Pool
A balcony with a view of the ocean and a sunset. There are two blue chairs and a small table with two cups.

19. 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
$139 nightly
The price is $148
Nov 1 - Nov 2
Total with taxes and fees
Pirates Cove Resort Studios
A resort with a swimming pool, multiple buildings, and a body of water.

20. Daytona 3BR Getaway Pool, Gym, Pet Friendly

Daytona 3BR Getaway Pool, Gym, Pet Friendly
3.0 star property
Daytona Beach
6.0 out of 10, (1 review)
"Apartment & location was excellent. The problem was that the temperatures during our stay was extremely cold. The HVAC wasn’t working properly & I couldn’t sleep the first night thinking the heater was going to blow up trying to get the room to an acceptable temperature. It ran for 12 hours straight overnight and only got the room slightly warm. To took another day to get the unit repaired. Thankfully the 2nd night was warm enough to sleep. I would definitely stay here again but would double...
United States
Jimmy
$346 nightly
The price is $360
Nov 25 - Nov 26
Total with taxes and fees
Daytona 3BR Getaway Pool, Gym, Pet Friendly
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

Holiday Inn Express & Suites Oceanfront by IHG

Holiday Inn Express & Suites Oceanfront by IHG

10/10 Excellent
"Nice ocean view"
Joseph 2-night trip
Posted 11 hours ago
Holiday Inn Express & Suites Oceanfront by IHG

Find out more about Osteen

Everything you need to know about Osteen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osteen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osteen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osteen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osteen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $75 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osteen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osteen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osteen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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.