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Holiday Rentals in Osceola County

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Our top choices for Osceola County holiday rentals

Indoor pool, outdoor pool
Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio

Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio

Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio
ARNOLDS PARK
10.0 out of 10, Exceptional, (76)
"Had a great time on our vacation. The cabin was great."
United States
Deborah B.
Beautiful 1500+ sq ft cabin with outdoor pool just steps off the patio
Pool
PRIME LOCATION AT BRIDGES BAY RESORT!!!

PRIME LOCATION AT BRIDGES BAY RESORT!!!

PRIME LOCATION AT BRIDGES BAY RESORT!!!
Arnolds Park
10.0 out of 10, Exceptional, (87)
"Nice, clean property located conveniently to water park/pool area. "
United States
Mike B.
PRIME LOCATION AT BRIDGES BAY RESORT!!!
Property grounds
Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes

Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes
Arnolds Park
10.0 out of 10, Exceptional, (95)
"We loved the condo. The views out the living room and deck are wonderful! Would definitely stay here again "
United States
Rhonda M.
The price is €472
includes taxes & fees
22 Dec - 23 Dec
Lakefront Luxury! Spacious corner condo, wrap around deck. 6 BB waterpark passes
Indoor pool, outdoor pool
Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat

Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat

Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat
Arnolds Park
9.8 out of 10, Exceptional, (134)
"Very clean and awesome location. "
United States
Joshua C.
Okoboji Bridges Bay Cabin 111~ Waterpark Passes and Relaxing Retreat
Indoor pool, outdoor pool
Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.

Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.
Arnolds Park
9.8 out of 10, Exceptional, (81)
"We enjoyed our stay! Beautiful view and living space."
United States
Josi J.
The price is €411
includes taxes & fees
28 Dec - 29 Dec
Penthouse Luxury with Lake Views & 6 FREE waterpark passes daily at Bridges Bay.
TV, fireplace, books
Morehead Retreat on 75 ft of East Lake Okoboji

Morehead Retreat on 75 ft of East Lake Okoboji

Morehead Retreat on 75 ft of East Lake Okoboji
2.0 star property
Spirit Lake
Morehead Retreat on 75 ft of East Lake Okoboji
Indoor pool, outdoor pool
Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB

Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB

Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB
Arnolds Park
10.0 out of 10, Exceptional, (53)
"The place was Wonderful. I would stay there again. Very close to the water park and restaurants."
United States
JoLynn H.
The price is €428
includes taxes & fees
21 Dec - 22 Dec
Penthouse Perfection-Spacious 4 Bedroom-Panoramic Views & Waterpark Passes at BB
Terrace/patio
Secluded Lakefront Lodge in Iowa's Great Lakes

Secluded Lakefront Lodge in Iowa's Great Lakes

Secluded Lakefront Lodge in Iowa's Great Lakes
Jackson
10.0 out of 10, Exceptional, (231)
"What a beautiful place to stay. We loved how it was nestled in the woods quiet and beautiful views of the lake. Spectacular sunrise viewsFishing wasn’t good but we enjoyed sitting on the dock. So much to do in the area too. Wineries and breweries and shops everywhere We loved it !"
United States
Joseph H.
Secluded Lakefront Lodge in Iowa's Great Lakes
Indoor pool, outdoor pool
Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.

Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.
Arnolds Park
10.0 out of 10, Exceptional, (166)
"Great stay! Beautiful condo with gorgeous view! Walking distance (about a mile) to plenty of activities. "
United States
Teresa L.
The price is €379
includes taxes & fees
27 Dec - 28 Dec
Lake view condo! Updated unit with 8 beds and 6 waterpark passes at Bridges Bay.
Property grounds
Amazing West Lake Okoboji Home! Location, Location, Location!!!

Amazing West Lake Okoboji Home! Location, Location, Location!!!

Amazing West Lake Okoboji Home! Location, Location, Location!!!
Arnolds Park
9.8 out of 10, Exceptional, (192)
"We enjoyed our stay! Thank you"
United States
Jill F.
Amazing West Lake Okoboji Home! Location, Location, Location!!!
Terrace/patio
Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities

Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities

Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities
Spirit Lake
9.8 out of 10, Exceptional, (12)
"Great place to stay!"
United States
Kamden C.
Cozy Lakeside Retreat with Beach Access, Scenic Views & Endless Amenities
Beach
Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!

Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!

Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!
Arnolds Park
10.0 out of 10, Exceptional, (117)
"Loved our time at stay-cation! This was such a great place to host our huge group. Plenty of space for everyone to hang out, play, sleep!"
United States
SummerB
The price is €625
includes taxes & fees
17 Dec - 18 Dec
Bring ALL of your family and friends to stay at the Central Stay Cation in Arnolds Park!
Interior
Quiet 1 bedroom in Milford

Quiet 1 bedroom in Milford

Quiet 1 bedroom in Milford
Milford
9.8 out of 10, Exceptional, (111)
"very centrally located with very accommodating hosts."
United States
sylvia w.
The price is €113
includes taxes & fees
16 Jan - 17 Jan 2026
Quiet 1 bedroom in Milford
Indoor pool, outdoor pool
Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.

Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.

Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.
Arnolds Park
10.0 out of 10, Exceptional, (85)
"We loved every minute of our stay! The place was so clean and prettier than the pictures. The hosts were so responsive and friendly! We will definitely stay there again! "
United States
Tayna R.
Lakefront BB Corner Condo. Expanded deck & panoramic views & 6 waterpark passes.
Indoor pool, outdoor pool
Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.

Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.

Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.
Arnolds Park
10.0 out of 10, Exceptional, (27)
"Beautiful and spacious property that was perfect for our family weekend getaway. Everything was as advertised and couldn't have been more happy with our stay. Property owners were great as well. Responded to us very quickly allowing us to have an earlier check-in and providing us more time to check-out! "
United States
Anonymous traveller
Spacious 4 Bedroom Lakefront Luxury. Panoramic Views & 6 waterpark passes at BB.
Outdoor dining
Spacioius Bridges Bay Cabin 3BR/2BA+loft for separate kids space - Sleeps 14

Spacioius Bridges Bay Cabin 3BR/2BA+loft for separate kids space - Sleeps 14

Spacioius Bridges Bay Cabin 3BR/2BA+loft for separate kids space - Sleeps 14
Arnolds Park
9.6 out of 10, Exceptional, (44)
"Great place to stay"
United States
Tammy B.
Spacioius Bridges Bay Cabin 3BR/2BA+loft for separate kids space - Sleeps 14
Pool
Bridges Bay Boji Lake-View Condo For Rent!!

Bridges Bay Boji Lake-View Condo For Rent!!

Bridges Bay Boji Lake-View Condo For Rent!!
Arnolds Park
9.8 out of 10, Exceptional, (126)
"Awesome place great people to work with! Will stay again!"
United States
Andrew V.
The price is €352
includes taxes & fees
22 Dec - 23 Dec
Bridges Bay Boji Lake-View Condo For Rent!!
Interior
Sandy Feet Retreat Lakefront on Big Spirit Lake

Sandy Feet Retreat Lakefront on Big Spirit Lake

Sandy Feet Retreat Lakefront on Big Spirit Lake
Spirit Lake
9.8 out of 10, Exceptional, (17)
"This was our fourth year at the house. Accommodations were very nice "
United States
Richard M.
Sandy Feet Retreat Lakefront on Big Spirit Lake
Interior
Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.

Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.

Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.
2.0 star property
Spirit Lake
10.0 out of 10, Exceptional, (4)
"This was a great place to stay. Sitting on the deck with the views of this calm section of the lake was a highlight of our vacation. "
United States
Amy F.
Beautiful, quiet and fully renovated lakehouse on East Okoboji Lake.
Indoor pool, outdoor pool
The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa

The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa

The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa
Arnolds Park
10.0 out of 10, Exceptional, (95)
"Very nice property, we enjoyed our stay there. "
United States
Joan M.
The Good Life Cabin - Bridges Bay Resort in Okoboji, Iowa
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 Osceola County Hotel Reviews

AmericInn by Wyndham Okoboji

AmericInn by Wyndham Okoboji

10/10 Excellent
"Everything was great during our last-minute stay. The woman at the front desk was very pleasant to work with, our room was great, the hotel was quiet, the pool area was nice (the sauna was an unexpected extra), and there was a great selection at breakfast. We would definitely stay again."
Rachel 1-night trip
Posted 7 days ago
AmericInn by Wyndham Okoboji

Find out more about Osceola County

Holiday Homes in Osceola County

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