Osteen Vacation Rentals

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Our top choices for Osteen vacation rentals

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, (271 reviews)
"Quiet area easy to access."
United States
Amanda
The price is CA $114
CA $187 total
includes taxes & fees
Jun 6 - Jun 7
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!

Boho Nights

Boho Nights
3.0 star property
Sanford
9.6 out of 10, Exceptional, (15 reviews)
"Great location very clean awesome decor "
United States
Heather
The price is CA $93
CA $197 total
includes taxes & fees
May 27 - May 28
Boho Nights

Bella Breeze

Bella Breeze
2.5 star property
Sanford
9.8 out of 10, Exceptional, (14 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 CA $79
CA $181 total
includes taxes & fees
May 28 - May 29
Bella Breeze

At the Center of it All!

At the Center of it All!
Indian River City
9.8 out of 10, Exceptional, (153 reviews)
"Great stay! Very responsive hosts! Would recommend and would stay again!"
United States
Jennifer C.
The price is CA $185
CA $319 total
includes taxes & fees
May 27 - May 28
At the Center of it All!

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 price is CA $91
CA $298 total
includes taxes & fees
May 27 - May 28
The Blue Aztec

The Cozy Crash Pad: Tiny House Experience

The Cozy Crash Pad: Tiny House Experience
Orlando
8.8 out of 10, Excellent, (25 reviews)
"The host communicated when needed. A great stay for a quick trip. "
United States
Jamee O.
The price is CA $88
CA $205 total
includes taxes & fees
Jun 1 - Jun 2
The Cozy Crash Pad: Tiny House Experience

Poolside Nights & Cozy Vibes — Book Now

Poolside Nights & Cozy Vibes — Book Now
Lake Mary
9.8 out of 10, Exceptional, (53 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is CA $124
CA $331 total
includes taxes & fees
May 27 - May 28
Poolside Nights & Cozy Vibes — Book Now

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
9.4 out of 10, Exceptional, (19 reviews)
"Wonderful host. Very comfortable accommodations. We enjoyed it very much."
United States
Bobbijo A.
The price is CA $134
CA $232 total
includes taxes & fees
May 31 - Jun 1
Luxury RV nested in a country setting, Only 9 minutes from Sanford airport!

Cozy Private Apartment - Stylish & Spotless — No sharing areas

Cozy Private Apartment - Stylish & Spotless — No sharing areas
Orlando
10.0 out of 10, Exceptional, (32 reviews)
"Awesome place to stay! Clean as a whistle, and nice and private! "
United States
N T.
The price is CA $117
CA $253 total
includes taxes & fees
May 31 - Jun 1
Cozy Private Apartment - Stylish & Spotless — No sharing areas

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (36 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is CA $199
CA $511 total
includes taxes & fees
May 30 - May 31
Incredible Private Lakefront Cottage Retreat

The Front Porch

The Front Porch
3.0 star property
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 CA $144
CA $277 total
includes taxes & fees
May 31 - Jun 1
The Front Porch

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, (20 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 CA $111
CA $199 total
includes taxes & fees
May 27 - May 28
A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

The Blue Aztec

The Blue Aztec
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 CA $97
CA $219 total
includes taxes & fees
May 27 - May 28
The Blue Aztec

Totally 80's

Totally 80's
3.0 star property
Sanford
8.4 out of 10, Very good, (10 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 $83
CA $186 total
includes taxes & fees
May 31 - Jun 1
Totally 80's

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
The price is CA $67
CA $219 total
includes taxes & fees
May 31 - Jun 1
Studio in the heart of Orlando

Spacious & Private Guest Pool House Oasis

Spacious & Private Guest Pool House Oasis
Union Park
9.8 out of 10, Exceptional, (22 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.
The price is CA $144
CA $375 total
includes taxes & fees
May 28 - May 29
Spacious & Private Guest Pool House Oasis

Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Unwind in DeLand: Fire Pit Nights & Downtown Delights!
Downtown DeLand Historic District
9.0 out of 10, Wonderful, (8 reviews)
"Wonderful quick getaway for the Microbrew fest."
United States
Paul E.
The price is CA $166
CA $322 total
includes taxes & fees
Jun 1 - Jun 2
Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Relax Tonight. Cozy, Quiet and Super Clean.

Relax Tonight. Cozy, Quiet and Super Clean.
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $124
CA $330 total
includes taxes & fees
Jun 7 - Jun 8
Relax Tonight. Cozy, Quiet and Super Clean.

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, (3 reviews)
"Absolutely beautiful! We loved it. The animals are wonderful. "
United States
Christin L.
The price is CA $137
CA $228 total
includes taxes & fees
May 29 - May 30
Mira Bella North - 1BR Tiny House in Lake Helen

Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside
Casselberry
9.4 out of 10, Exceptional, (10 reviews)
"Good location, just off 436. Safe, quiet neighborhood."
United States
Dwain H.
The price is CA $93
CA $194 total
includes taxes & fees
Jun 8 - Jun 9
Traveler's Dream: Refresh & Recharge Poolside
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?

Daytona Beach XI: Visitors like this Osteen vacation home rental. It is located by the ocean and offers an arcade game room, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings.

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 Ashby Park and Lake Jesup Conservation Area 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.