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

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, (4 reviews)
"Absolutely beautiful! We loved it. The animals are wonderful. "
United States
Christin L.
$149 nightly
The price is $165
Jul 8 - Jul 9
Total with taxes and fees
Mira Bella North - 1BR Tiny House in Lake Helen

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (153 reviews)
"It was a great place for us to stay at, with all of the space coast's things to do. The hosts were great, very attentive and gracious."
United States
Ryan C.
$189 nightly
The price is $209
Jul 6 - Jul 7
Total with taxes and fees
At the Center of it All!

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very Good, (10 reviews)
"Great location to downtown Sanford!"
United States
Kathleen
$128 nightly
The price is $143
Jul 12 - Jul 13
Total with taxes and fees
Totally 80's

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Whispering Oaks
9.2 out of 10, Wonderful, (273 reviews)
"Quiet area easy to access."
United States
Amanda
$119 nightly
The price is $131
Aug 3 - Aug 4
Total with taxes and fees
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (59 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
$234 nightly
The price is $259
Jul 6 - Jul 7
Total with taxes and fees
Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
$310 nightly
The price is $343
Jul 5 - Jul 6
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat

Catalina Beach Club

Catalina Beach Club
3.5 star property
Daytona Beach
10.0 out of 10, Exceptional, (1 review)
"Beautiful views. The room was clean and everyone was so sweet"
United States
Brandy
$135 nightly
The price is $152
Jul 6 - Jul 7
Total with taxes and fees
Catalina Beach Club

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
$205 nightly
The price is $230
Jul 5 - Jul 6
Total with taxes and fees
The Front Porch

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
$220 nightly
The price is $237
Jul 8 - Jul 9
Total with taxes and fees
The Blue Aztec

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (25 reviews)
"The pool house looked exactly like the pictures and it was a very comfortable place to stay. My husband and I really enjoyed it and would definitely stay there again in the future."
United States
Dionne T.
$243 nightly
The price is $269
Jul 5 - Jul 6
Total with taxes and fees
Spacious & Private Guest Pool House Oasis

Bella Breeze

Bella Breeze
2.5 star property
Downtown Sanford
9.6 out of 10, Exceptional, (17 reviews)
"Great location for restaurants and river trail. Very well stocked so it is an easy and comfortable stay."
United States
Nancy
$130 nightly
The price is $146
Jul 5 - Jul 6
Total with taxes and fees
Bella Breeze

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
$213 nightly
The price is $236
Jul 6 - Jul 7
Total with taxes and fees
Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Boho Nights

Boho Nights
3.0 star property
Downtown Sanford
9.6 out of 10, Exceptional, (16 reviews)
"Great stay!"
United States
Nicholas
$143 nightly
The price is $160
Jul 23 - Jul 24
Total with taxes and fees
Boho Nights

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.
$135 nightly
The price is $149
Jul 7 - Jul 8
Total with taxes and fees
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

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
$131 nightly
The price is $145
Jul 8 - Jul 9
Total with taxes and fees
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Studio in the heart of Orlando

Studio in the heart of Orlando
Azalea Park
9.4 out of 10, Exceptional, (6 reviews)
"Can’t complain. Would re book for sure."
United States
Matthew
$160 nightly
The price is $160
Jul 23 - Jul 24
Total with taxes and fees
Studio in the heart of Orlando

Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Unwind in DeLand: Fire Pit Nights & Downtown Delights!
Downtown DeLand Historic District
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful quick getaway for the Microbrew fest."
United States
Paul E.
$205 nightly
The price is $228
Jul 5 - Jul 6
Total with taxes and fees
Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Silver Beach Club

Silver Beach Club
3.0 star property
Daytona Beach
8.6 out of 10, Excellent, (125 reviews)
"Great place "
United States
JohnAaron
$85 nightly
The price is $96
Jul 13 - Jul 14
Total with taxes and fees
Silver Beach Club

The Jazz Loft

The Jazz Loft
3.0 star property
Downtown Sanford
8.8 out of 10, Excellent, (9 reviews)
"Location, location, location!!! What a cute and fun space. I thoroughly enjoyed my entire Jazz Loft experience. Look fwd to next trip! "
United States
Deborah
$130 nightly
The price is $145
Jul 5 - Jul 6
Total with taxes and fees
The Jazz Loft

Hello Sunshine 321.. Lift Off

Hello Sunshine 321.. Lift Off
Royal Oak Golf Country Club
8.8 out of 10, Excellent, (23 reviews)
"Great location for the wedding we attended. Perfect size for our quick trip. We enjoyed staying here."
United States
Ed S.
$310 nightly
The price is $342
Jul 6 - Jul 7
Total with taxes and fees
Hello Sunshine 321.. Lift Off
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 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 $96 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.

Explore a world of travel with Expedia

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.