Osteen Vacation Rentals from $96: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Osteen vacation rentals

1 bedroom, iron/ironing board, free WiFi, bed sheets

Mira Bella North - 1BR Tiny House in Lake Helen

Lake Helen

Christin L.

$149 nightly

Jul 8 - Jul 9

Total with taxes and fees

At the Center of it All!

Indian River City

Ryan C.

$189 nightly

Jul 6 - Jul 7

Total with taxes and fees

Totally 80's

Sanford

Kathleen

$128 nightly

Jul 12 - Jul 13

Total with taxes and fees

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

Whispering Oaks

Amanda

$119 nightly

Aug 3 - Aug 4

Total with taxes and fees

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

Lake Mary

Jaelyn M.

$234 nightly

Jul 6 - Jul 7

Total with taxes and fees

Incredible Private Lakefront Cottage Retreat

Altamonte Springs

Lisa

$310 nightly

Jul 5 - Jul 6

Total with taxes and fees

One Bedroom Two Bathroom Deluxe Oceanfront Suite | Living area | 50-inch flat-screen TV with cable channels, DVD player

Catalina Beach Club

Daytona Beach

Brandy

$135 nightly

Jul 6 - Jul 7

Total with taxes and fees

The Front Porch

Downtown Sanford

Johnny

$205 nightly

Jul 5 - Jul 6

Total with taxes and fees

Standard Apartment | Living area | 50-inch LCD TV with digital channels, Netflix, streaming services

The Blue Aztec

Downtown Sanford

Lisa

$220 nightly

Jul 8 - Jul 9

Total with taxes and fees

Spacious & Private Guest Pool House Oasis

Union Park

Dionne T.

$243 nightly

Jul 5 - Jul 6

Total with taxes and fees

Bella Breeze

Downtown Sanford

Nancy

$130 nightly

Jul 5 - Jul 6

Total with taxes and fees

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

Lake Mary

Tricia S.

$213 nightly

Jul 6 - Jul 7

Total with taxes and fees

Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services

Boho Nights

Downtown Sanford

Nicholas

$143 nightly

Jul 23 - Jul 24

Total with taxes and fees

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

Lake Helen

Stacy S.

$135 nightly

Jul 7 - Jul 8

Total with taxes and fees

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Deltona

Kimberly

$131 nightly

Jul 8 - Jul 9

Total with taxes and fees

Studio in the heart of Orlando

Azalea Park

Matthew

$160 nightly

Jul 23 - Jul 24

Total with taxes and fees

Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Downtown DeLand Historic District

Paul E.

$205 nightly

Jul 5 - Jul 6

Total with taxes and fees

Silver Beach Club

Daytona Beach

JohnAaron

$85 nightly

Jul 13 - Jul 14

Total with taxes and fees

The Jazz Loft

Downtown Sanford

Deborah

$130 nightly

Jul 5 - Jul 6

Total with taxes and fees

Hello Sunshine 321.. Lift Off

Royal Oak Golf Country Club

Ed S.

$310 nightly

Jul 6 - Jul 7

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Osteen Hotel Reviews

Hilton Orlando/Altamonte Springs

10/10 Excellent

"Excellent"

Nautilus Inn

10/10 Excellent

"I have stayed at this property many times and it never disappoints. The beach access is what I appreciate the most. Being able to stay in a hotel and walk directly to the beach less than 2 to 3 minutes time is the ultimate convenience for me. They have a spray section to remove all sand from yourself and your chairs, boogie boards, etc. The staff is always friendly. Great place for a great price. My only 95 stars would be the cleanliness of the bathroom. It left a little to be desired. It also seemed like they renovated the room, but did not upgrade the bathrooms which I found interesting. But I look forward to going back there again."

HomeTowne Studios by Red Roof Orlando - UCF Area

8/10 Good

"The staff was great, including the office during check in and the property maintenance that helped me early morning to check out before the office opened. The property itself is decently maintained, considering it's an older property. Has a fridge, sink, and microwave in the unit. Cleaning could have been a little deeper/better for the bathroom. Pricing was fair and matches the unit. Overall 4/5 for me and would stay her again in the future."

Bahama House

10/10 Excellent

"We chose to stay here because of the location and all the incredible Google reviews—and those 5-star reviews were absolutely right! We had an amazing stay. Everything was spotless and felt fresh the moment we walked in. My daughter especially loved playing the piano in the lobby, which was such a nice touch. Breakfast was excellent, and the hot pancakes were exactly what we were hoping for! We booked a partial ocean view room, but thanks to the hotel's layout, it felt more like a full ocean view. The balcony was fantastic, and we spent a lot of time enjoying it. The only minor downside was that, although I have a medical marijuana card for my neck injuries, smoking wasn't permitted on the balcony. Aside from that, everything was perfect, and we'd definitely stay here again!"

Days Inn by Wyndham Daytona Oceanfront

10/10 Excellent

"I think we are in the double digits regarding the number of times we have stayed here. Love the hot tub. Rooms are clean and comfortable. The staff is always friendly and professional - available to assist with any needs. We get the efficiency oceanfront. It’s nice having the larger refrigerator and oven to heat up leftovers. Will be coming back in September & November."

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.

Osteen Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Osteen vacation rentals

Mira Bella North - 1BR Tiny House in Lake Helen

At the Center of it All!

Totally 80's

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

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

Incredible Private Lakefront Cottage Retreat

Catalina Beach Club

The Front Porch

The Blue Aztec

Spacious & Private Guest Pool House Oasis

Bella Breeze

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

Boho Nights

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

A Tranquil Hideaway in a peaceful, quiet Deltona neighborhood

Studio in the heart of Orlando

Unwind in DeLand: Fire Pit Nights & Downtown Delights!

Silver Beach Club

The Jazz Loft

Hello Sunshine 321.. Lift Off

Find vacation rentals that suit your style

Top Osteen Hotel Reviews

Hilton Orlando/Altamonte Springs

Find out more about Osteen

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app