Osteen Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Osteen vacation rentals

Basic Studio | Terrace/patio
Silver Beach Club

Silver Beach Club

Silver Beach Club
3.0 star property
Daytona Beach
8.6 out of 10, Excellent, (72)
"Got the Two-Bedroom family suite was very roomy, The pool was nice. The hot tub wasn't working ,we had direct assets to the beaches, the staff was outstanding "
United States
Vickie
The price is ￥11,562
￥13,008 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Silver Beach Club
Exterior
Ocean Beach Club

Ocean Beach Club

Ocean Beach Club
2.5 star property
Coronado Beach
10.0 out of 10, Exceptional, (1)
"Great spot, clean room, would love to stay again. "
United States
james
The price is ￥18,833
￥36,784 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Ocean Beach Club
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers
Shoreline Suites & Cabana Cottages

Shoreline Suites & Cabana Cottages

Shoreline Suites & Cabana Cottages
2.0 star property
Daytona Beach Shores
8.8 out of 10, Excellent, (380)
"Love the location and how cute the cabanas are. "
United States
Jennifer
The price is ￥17,560
￥21,515 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Shoreline Suites & Cabana Cottages
Exterior
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!

Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Whispering Oaks
9.2 out of 10, Wonderful, (241)
"We had a pleasant and comfortable stay. This cost less than a night at a Country Inn and Suites we were looking at but we all got our own bedroom. The beds were comfortable. I would definitely stay at this house again if in the area."
United States
Sherry
The price is ￥10,528
￥18,406 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Mid Century Charm! KSC,Port Canaveral,Cocoa and Bio-Lume Kayak,Pet Friendly!
Outdoor pool, sun loungers
Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort

Tropical Suites at Sunglow Resort
4.5 star property
Daytona Beach Shores
8.6 out of 10, Excellent, (61)
"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
Tropical Suites at Sunglow Resort
Indoor pool, outdoor pool
~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~

~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~
Bostwick Park
8.8 out of 10, Excellent, (38)
"We were initially surprised at the size of this "
United States
Helen P.
The price is ￥6,239
￥23,299 total
includes taxes & fees
Jan 8 - Jan 9, 2026
~ Ocean ~ Daze ~ Hideaway ~ Modern Studio near the Beach ~
Terrace/patio
“NATURE IN THE CITY”

“NATURE IN THE CITY”

“NATURE IN THE CITY”
2.0 star property
Union Park
9.0 out of 10, Wonderful, (6)
" Did not expect to be in someone’s back yard but overall was a pleasant stay. "
United States
Jola L.
The price is ￥11,932
￥34,401 total
includes taxes & fees
Jan 9 - Jan 10, 2026
“NATURE IN THE CITY”
Beach/ocean view
Fantasy Island Resort, Daytona Beach Shores

Fantasy Island Resort, Daytona Beach Shores

Fantasy Island Resort, Daytona Beach Shores
4.0 star property
Rio Mar Beaches
8.8 out of 10, Excellent, (113)
"Clean room polite staff good amenities. "
United States
Werner
Fantasy Island Resort, Daytona Beach Shores
Indoor pool, outdoor pool
Sea ~ Side ~ Hideaway ~ Studio Condo ~ near the Beach ~

Sea ~ Side ~ Hideaway ~ Studio Condo ~ near the Beach ~

Sea ~ Side ~ Hideaway ~ Studio Condo ~ near the Beach ~
Bostwick Park
9.6 out of 10, Exceptional, (21)
"We enjoyed our two night stay. "
United States
Dave H.
The price is ￥7,829
￥25,150 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sea ~ Side ~ Hideaway ~ Studio Condo ~ near the Beach ~
A heated pool
DIRECT OCEANFRONT CORNER UNIT - OCEAN VIEWS FROM LIVING ROOM AND BEDROOM

DIRECT OCEANFRONT CORNER UNIT - OCEAN VIEWS FROM LIVING ROOM AND BEDROOM

DIRECT OCEANFRONT CORNER UNIT - OCEAN VIEWS FROM LIVING ROOM AND BEDROOM
Daytona Beach
10.0 out of 10, Exceptional, (112)
"this place was exactly as advertised it was great."
United States
carol r.
DIRECT OCEANFRONT CORNER UNIT - OCEAN VIEWS FROM LIVING ROOM AND BEDROOM
Property grounds
#163 Ocean Jewel

#163 Ocean Jewel

#163 Ocean Jewel
South Peninsula Historic District
8.8 out of 10, Excellent, (30)
"Great place"
United States
Jasmin
The price is ￥8,578
￥25,930 total
includes taxes & fees
Jan 11 - Jan 12, 2026
#163 Ocean Jewel
Terrace/patio
The Front Porch

The Front Porch

The Front Porch
3.0 star property
Sanford
10.0 out of 10, Exceptional, (2)
"What a great space. 2 big bedrooms, and a great front porch apace with a hammock to watch the sunrise. Quite street just blocks from the center of downtown Sanford. I've used their properties 8-10 tines and ive never been disappointed. "
United States
Patrick
The Front Porch
1 bedroom, desk, iron/ironing board, free WiFi
Clean Luxury Boho in Orlando 25 min from Theme Parks

Clean Luxury Boho in Orlando 25 min from Theme Parks

Clean Luxury Boho in Orlando 25 min from Theme Parks
2.0 star property
Orlando
10.0 out of 10, Exceptional, (1)
"It served its purpose for 2 nights. Wouldn’t recommend more than 2 people. Clean cozy and had come coffee in there. Very nice and responsive host. Perfect for a quick trip as it is on the smaller side but again it was perfect for my stay. "
United States
Mackenzie H.
The price is ￥10,224
￥30,237 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Clean Luxury Boho in Orlando 25 min from Theme Parks
Property grounds
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
2.0 star property
Deltona
9.6 out of 10, Exceptional, (4)
"Loved the proximity to the wonderful bike and walking trail!"
United States
Sharon H.
The price is ￥20,120
￥54,004 total
includes taxes & fees
Jan 6 - Jan 7, 2026
COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House

The Sanford Foodie Guest House

The Sanford Foodie Guest House
Sanford
8.8 out of 10, Excellent, (15)
"Cozy little place to stay"
United States
Ruth P.
The price is ￥8,206
￥21,919 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Sanford Foodie Guest House
Premium Studio, 2 Queen Beds, Kitchen, Ocean View | Desk, soundproofing, iron/ironing board, free WiFi
Pirates Cove Resort Studios

Pirates Cove Resort Studios

Pirates Cove Resort Studios
3.0 star property
Daytona Beach Shores
6.4 out of 10, (145)
"The room was clean and in a wonderful spot. Clean and easy access. I will be booking here again."
United States
Kiya
The price is ￥10,918
￥23,045 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Pirates Cove Resort Studios
Exterior
Totally 80's

Totally 80's

Totally 80's
3.0 star property
Sanford
9.4 out of 10, Exceptional, (3)
"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 ￥12,478
￥24,457 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Totally 80's
Pool
Beachfront Suite in Daytona Beach, FL with Ocean Views!

Beachfront Suite in Daytona Beach, FL with Ocean Views!

Beachfront Suite in Daytona Beach, FL with Ocean Views!
Daytona Beach
9.4 out of 10, Exceptional, (10)
"Perfect place! My husband and I enjoyed our stay. The balcony facing the beach was amazing!! Overalll would stay there again :) "
United States
Savannah T.
The price is ￥7,959
￥27,689 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Beachfront Suite in Daytona Beach, FL with Ocean Views!
Beach nearby, sun loungers
LaLa`s Beach House - Walking Distance to the Beach and Shopping

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, (36)
"much needed getaway! Lala's is comfortable, clean, fun, relaxing. Everything a beach getaway should be! "
United States
Stephanie S.
The price is ￥11,105
￥42,460 total
includes taxes & fees
Jan 13 - Jan 14, 2026
LaLa`s Beach House - Walking Distance to the Beach and Shopping
Standard Apartment | Living area | 50-inch LED TV with digital channels, Netflix, streaming services
Boho Nights

Boho Nights

Boho Nights
3.0 star property
Sanford
9.0 out of 10, Wonderful, (7)
"Wonderful spot, and excellent hosts!"
United States
Thomas
Boho Nights
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

Days Inn by Wyndham Daytona Oceanfront

Days Inn by Wyndham Daytona Oceanfront

10/10 Excellent
"Everything very clean "
Viviana 1-night trip
Posted 23 hours ago
Days Inn by Wyndham Daytona Oceanfront

Find out more about Osteen

Search for holiday rentals in Osteen on Expedia! You can easily find your home rentals, villas, holiday apartments in Osteen using one of the methods below:

  • View our selection of featured holiday rentals in Osteen
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Look no further and take a look at our great range of rental properties in Osteen!

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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: You might want to consider this vacation home rental near Osteen, which 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.