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

Osteen Holiday Rentals

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Our top choices for Osteen holiday rentals

Howard Johnson by Wyndham Oceanfront Daytona Beach

Howard Johnson by Wyndham Oceanfront Daytona Beach
2.0 star property
South Peninsula Historic District
6.8 out of 10, (9 reviews)
"My family and I really enjoyed our stay. The room was spacious and accommodating at a very forgiving rate. The view was gorgeous and the beach was close by. We look forward to vacationing here again."
United States
Darla
The price is AU$113
includes taxes & fees
14 Aug - 15 Aug
Howard Johnson by Wyndham Oceanfront Daytona Beach

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (18 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
The price is AU$205
includes taxes & fees
26 July - 27 July
Bella Breeze

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 AU$202
includes taxes & fees
26 July - 27 July
Boho Nights

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 AU$232
includes taxes & fees
28 July - 29 July
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

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 AU$314
includes taxes & fees
13 Aug - 14 Aug
The Front Porch

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 AU$194
includes taxes & fees
26 July - 27 July
The Jazz Loft

The Blue Aztec

The Blue Aztec
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The price is AU$305
includes taxes & fees
26 July - 27 July
The Blue Aztec

Serenity @ Court

Serenity @ Court
Sanford
10.0 out of 10, Exceptional, (15 reviews)
"The stay was very pleasurable. We plan to stay here again soon."
United States
William W.
The price is AU$287
includes taxes & fees
7 Aug - 8 Aug
Serenity @ Court

River City Retreat

River City Retreat
Sanford
9.6 out of 10, Exceptional, (17 reviews)
"Great place and quick, simple check in."
United States
Dennis L.
The price is AU$315
includes taxes & fees
31 July - 1 Aug
River City Retreat

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 place to stay near the airport "
United States
Rodney
The price is AU$528
includes taxes & fees
28 July - 29 July
Tranquil 3-bedroom house in Sanford with AC, WiFi

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 AU$193
includes taxes & fees
4 Aug - 5 Aug
Totally 80's

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 price is AU$230
includes taxes & fees
26 July - 27 July
The Blue Aztec

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 AU$175
includes taxes & fees
7 Aug - 8 Aug
Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

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, (25 reviews)
"Great host "
United States
jordan l.
The price is AU$568
includes taxes & fees
27 July - 28 July
Historic Downtown Sanford Sunshine Cottage with Tree Top Suite!

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, (61 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is AU$384
includes taxes & fees
5 Aug - 6 Aug
Lake Mary Pool Days & Hammock Naps Book Your Escape Before It’s Gone

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 AU$202
includes taxes & fees
27 July - 28 July
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Home Sweet Home

Home Sweet Home
Sanford
9.2 out of 10, Wonderful, (30 reviews)
"Very comfortable and clean home! "
United States
Stacy B.
The price is AU$480
includes taxes & fees
5 Aug - 6 Aug
Home Sweet Home

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 2-bedroom apartment with WiFi, AC in lovely Orlando
Orlando
9.8 out of 10, Exceptional, (12 reviews)
"Very clean and hospitable. Recommend staying here for sure!"
United States
Kyle Y.
The price is AU$371
includes taxes & fees
5 Aug - 6 Aug
Charming 2-bedroom apartment with WiFi, AC in lovely Orlando

Charming 3-bedroom home away from home.

Charming 3-bedroom home away from home.
Chuluota
9.8 out of 10, Exceptional, (25 reviews)
"Great layout, clean, plenty of amenities, quiet neighborhood. Host was very friendly and responsive. "
United States
Mary B.
The price is AU$532
includes taxes & fees
29 July - 30 July
Charming 3-bedroom home away from home.

Mira Bella North - 1BR Tiny House in Lake Helen

Mira Bella North - 1BR Tiny House in Lake Helen
Lake Helen
10.0 out of 10, Exceptional, (5 reviews)
"From the start of our stay until the end, our host was amazing. The property is beautiful. You will love this property!"
United States
Angel
The price is AU$239
includes taxes & fees
4 Aug - 5 Aug
Mira Bella North - 1BR Tiny House in Lake Helen
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

Everything you need to know about Osteen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osteen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osteen holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osteen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osteen holiday rentals we have selected for you start as low as AU$154 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osteen rentals

At Expedia, we put the best Osteen holiday 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 holiday.

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. 

Frequently asked questions

Can I find holiday rentals in Osteen?

Yes, there are holiday rentals in Osteen close to Pell's Citrus & Nursery, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osteen has to offer?

Pirates Cove Resort Studios: This holiday home rental outside of Osteen 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 holiday rentals are there in Osteen?

Expedia has 3 holiday 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 holiday rental in Osteen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osteen. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for families.