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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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 P4,652
P9,298 total
includes taxes & fees
Aug 12 - Aug 13
Bella Breeze
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 P4,652
P9,298 total
includes taxes & fees
Aug 10 - Aug 11
Boho Nights
2 bedrooms, desk, WiFi (free)

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 P7,663
P13,691 total
includes taxes & fees
Aug 10 - Aug 11
The Front Porch
Living area

4. 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 P4,652
P13,859 total
includes taxes & fees
Aug 9 - Aug 10
The Blue Aztec
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 P4,379
P8,991 total
includes taxes & fees
Aug 9 - Aug 10
The Jazz Loft
Exterior

6. The Contemporary

The Contemporary
3.0 star property
Downtown Sanford
The price is P7,663
P17,230 total
includes taxes & fees
Aug 10 - Aug 11
The Contemporary
Interior

7. 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 P4,105
P8,685 total
includes taxes & fees
Aug 9 - Aug 10
Totally 80's
Living area

8. 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 P4,379
P13,552 total
includes taxes & fees
Aug 16 - Aug 17
The Mellow Yellow
WiFi (free)

9. Cozy Modern Studio

Cozy Modern Studio
2.0 star property
Casselberry
The price is P4,433
P9,527 total
includes taxes & fees
Aug 11 - Aug 12
Cozy Modern Studio
Interior

10. Walk to Lake: Stunning Central Florida Home!

Walk to Lake: Stunning Central Florida Home!
3.0 star property
Lake Mary
The price is P23,962
P45,169 total
includes taxes & fees
Aug 16 - Aug 17
Walk to Lake: Stunning Central Florida Home!
View from room

11. Oceania III

Oceania III
3.0 star property
Central Beach
9.8 out of 10, Exceptional, (7 reviews)
"Very nice location and great front desk staff. Queen bed needs repair/replace. Kinf was great!"
United States
Micheal
The price is P12,544
P30,662 total
includes taxes & fees
Aug 23 - Aug 24
Oceania III
Living area

12. Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
8.8 out of 10, Excellent, (13 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 P7,072
P7,956 total
includes taxes & fees
Aug 23 - Aug 24
Catalina Beach Club
2 bedrooms

13. Stunning Hacienda at La Cita Country Club

Stunning Hacienda at La Cita Country Club
2.0 star property
La Cita
The price is P8,098
P19,165 total
includes taxes & fees
Aug 11 - Aug 12
Stunning Hacienda at La Cita Country Club
Terrace/patio

14. 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 P4,744
P9,533 total
includes taxes & fees
Aug 9 - Aug 10
Pirates Cove Resort Studios
Balcony view

15. Beautiful Beachfront Resort Condo

Beautiful Beachfront Resort Condo
3.0 star property
Daytona Beach
9.0 out of 10, Wonderful, (17 reviews)
"Beyond expectations!!!"
Canada
Sara
The price is P8,210
P16,078 total
includes taxes & fees
Aug 9 - Aug 10
Beautiful Beachfront Resort Condo
Terrace/patio

16. Beach Front Studios in Daytona Beach

Beach Front Studios in Daytona Beach
3.0 star property
Daytona Beach
7.6 out of 10, Good, (175 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 P4,754
P9,555 total
includes taxes & fees
Aug 9 - Aug 10
Beach Front Studios in Daytona Beach
Balcony view

17. Castaways Resort Studios

Castaways Resort Studios
3.0 star property
Daytona Beach Shores
6.0 out of 10, (115 reviews)
"The room was perfect for our weekend stay. It had all your home necessities. I will be booking again real soon. "
United States
Jeana
The price is P3,831
P8,507 total
includes taxes & fees
Aug 9 - Aug 10
Castaways Resort Studios
Terrace/patio

18. 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 P7,121
P8,011 total
includes taxes & fees
Aug 9 - Aug 10
Shoreline Suites & Cabana Cottages
Floor plan

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

Daytona 2BR Getaway Parking Family & Pet-friendly
3.0 star property
Daytona Beach
The price is P9,141
P23,176 total
includes taxes & fees
Aug 31 - Sep 1
Daytona 2BR Getaway Parking Family & Pet-friendly
Exterior

20. 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, (132 reviews)
"Room was clean and hotel was conveniently located on the beach."
United States
David J.
The price is P5,172
P7,871 total
includes taxes & fees
Aug 23 - Aug 24
Fantasy Island Resort, Daytona Beach Shores
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

Home2 Suites by Hilton Daytona Beach Speedway

Home2 Suites by Hilton Daytona Beach Speedway

10/10 Excellent
"Buena atención del team y el lugar bien ubicado."
Ramber 1-night trip
Posted less than an hour ago
Home2 Suites by Hilton Daytona Beach Speedway

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:

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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?

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 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.