Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

Ocean Beach Club

Ocean Beach Club
2.5 star property
Coronado Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great spot, clean room, would love to stay again. "
United States
james
The price is CA $293
CA $467 total
includes taxes & fees
Feb 17 - Feb 18
Ocean Beach Club

Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort
4.5 star property
Daytona Beach Shores
8.6 out of 10, Excellent, (61 reviews)
"The hotel was so clean and it had a nice pool. The staff were so friendly and helpful! Will definitely stay again in the future!"
United States
Michaela
The price is CA $98
CA $432 total
includes taxes & fees
Feb 10 - Feb 11
Tropical Suites at Sunglow Resort

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, (248 reviews)
"Very clean and comfortable place to spend a night before our cruise. Beds were really comfortable "
United States
Fred
The price is CA $157
CA $234 total
includes taxes & fees
Mar 2 - Mar 3
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Totally 80's

Totally 80's
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 reviews)
"Cute, clean, and comfortable. Located in a safe neighborhood, the house had everything we needed for a great stay. Communication was timely and smooth—highly recommend."
United States
Serge
The price is CA $98
CA $202 total
includes taxes & fees
Mar 9 - Mar 10
Totally 80's

Charming hotel suite with AC and WiFi in delightful Titusville

Charming hotel suite with AC and WiFi in delightful Titusville
Titusville
The price is CA $92
CA $161 total
includes taxes & fees
Feb 13 - Feb 14
Charming hotel suite with AC and WiFi in delightful Titusville

“NATURE IN THE CITY”

“NATURE IN THE CITY”
Union Park
9.0 out of 10, Wonderful, (6 reviews)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is CA $105
CA $303 total
includes taxes & fees
Feb 10 - Feb 11
“NATURE IN THE CITY”

The Blue Aztec

The Blue Aztec
3.0 star property
Sanford
9.6 out of 10, Exceptional, (13 reviews)
"Great location! Great Dining! "
United States
Lisa
The Blue Aztec

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!
Geneva
9.6 out of 10, Exceptional, (17 reviews)
"This place was perfect for me and my dad and my son to stay at while my son played ball close by."
United States
Kevin D.
The price is CA $122
CA $217 total
includes taxes & fees
Feb 17 - Feb 18
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

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, (37 reviews)
"Very nice clean cottage in a quiet secluded location. "
United States
Ervin M.
The price is CA $123
CA $204 total
includes taxes & fees
Feb 17 - Feb 18
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Front Porch

The Front Porch
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3 reviews)
"Enjoyed the place. Nice and relaxing. Close to downtown and lots of options for food. "
United States
Johnny
The Front Porch

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.2 out of 10, Wonderful, (62 reviews)
"It was a good area to stay "
United States
Christanah O.
The price is CA $111
CA $213 total
includes taxes & fees
Mar 11 - Mar 12
Tiny Hidden Cottage

Silver Beach Club

Silver Beach Club
3.0 star property
Daytona Beach
8.4 out of 10, Very good, (83 reviews)
"Room/building is older, but clean. Front desk staff were excellent."
United States
Daniel
The price is CA $129
CA $146 total
includes taxes & fees
Feb 10 - Feb 11
Silver Beach Club

Clean Luxury Boho in Orlando 25 min from Theme Parks

Clean Luxury Boho in Orlando 25 min from Theme Parks
Orlando
10.0 out of 10, Exceptional, (2 reviews)
"The room was beautifully decorated and SPOTLESS. Just what we needed. Close to the airport and highways. Highly recommend."
United States
Leslie
The price is CA $90
CA $268 total
includes taxes & fees
Feb 17 - Feb 18
Clean Luxury Boho in Orlando 25 min from Theme Parks

Boho Nights

Boho Nights
3.0 star property
Sanford
9.2 out of 10, Wonderful, (10 reviews)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights

The Jazz Loft

The Jazz Loft
3.0 star property
Sanford
8.4 out of 10, Very good, (7 reviews)
"Amazing! They had everything I needed and were so flexible as I almost needed to extend my stay due to the storm. The vibe was great, very cool and seamless check in and access. Close to everything needed. I will definitely be returning! Can’t wait."
United States
Rae
The Jazz Loft

Down town historic Titusville. apt B Private no Host.

Down town historic Titusville. apt B Private no Host.
Le Barons Of Titusville
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable. "
United States
Shelly K.
The price is CA $108
CA $283 total
includes taxes & fees
Feb 22 - Feb 23
Down town historic Titusville. apt B Private no Host.

LaLa`s Beach House - Walking Distance to the Beach and Shopping

LaLa`s Beach House - Walking Distance to the Beach and Shopping
Central Beach
9.8 out of 10, Exceptional, (37 reviews)
"much needed getaway! Lala's is comfortable, clean, fun, relaxing. Everything a beach getaway should be! "
United States
Stephanie S.
The price is CA $109
CA $390 total
includes taxes & fees
Feb 10 - Feb 11
LaLa`s Beach House - Walking Distance to the Beach and Shopping

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.6 out of 10, Exceptional, (8 reviews)
"Cute little cottage with basic amenities. Very convenient location to get to Sanford airport. Would definitely stay again. "
United States
Jacob
Bella Breeze

Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀
Orlando
9.6 out of 10, Exceptional, (13 reviews)
"The property was immaculately clean, stylish, roomy and private! It was so convenient to everything yet on the outskirts in a quiet peaceful neighborhood. "
United States
KELLY Z.
The price is CA $80
CA $233 total
includes taxes & fees
Feb 11 - Feb 12
Sunshine Escape Guesthouse ☀

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (29 reviews)
"Mercedes is an amazing host and has thought of - and provided EVERYTHING you need for a fantastic stay. Would ABSOLUTELY stay here again and HIGHLY recommend!!"
United States
Rick K.
The price is CA $116
CA $250 total
includes taxes & fees
Feb 10 - Feb 11
Cozy Private Apartment - Stylish & Spotless — No sharing areas
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?

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 Monroe Conservation Area and Lake Jesup 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.