Sister Bay Condo Rentals - Vacation Rentals in Osborne House

Beautiful Frank James Court From US $168
         

8.6 (23 Reviews)
House
  • Parking
  • View
  • Ocean View
Holly Tree House From US $235
         

|
10.0 (24 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Security/Safety
Nutcroft From US $154
         

|
8.2 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • Child Friendly
Medina by The Solent From US $431
         

10.0 (1 Review)
Cottage
  • Parking
  • Pet Friendly
  • View
Mulberry Cottage coastal holiday home From US $279
         

9.4 (10 Reviews)
Cottage
  • TV
  • View
  • Ocean View
Blue Winds and Waves From US $174
         

|
9.2 (36 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • View
The Caledon From US $135
         

|
9.8 (127 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility
Solent View Apartment From US $459
         

10.0 (25 Reviews)
Apartment
  • Parking
  • Balcony/Terrace
  • Security/Safety
7 bedroom accommodation in Wootton Bridge, near Ryde From US $756
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
3 bedroom accommodation in Wootton, near Ryde From US $389
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
Red Squirrel Lodge - UKC677 From US $172
         

10.0 (2 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
2 bedroom accommodation in Wootton Bridge From US $142
         

9.0 (12 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Security/Safety
2 bedroom accommodation in Wootton Bridge, near Ryde From US $247
         

New
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
Bodwen Corner Cottage From US $241
         

10.0 (7 Reviews)
Cottage
  • Parking
  • Balcony/Terrace
  • Security/Safety
3 bedroom accommodation in East Cowes From US $142
         

10.0 (8 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace
2 bedroom accommodation in Island Harbour, near Newport From US $130
         

9.0 (8 Reviews)
Cottage
  • Pet Friendly
  • Balcony/Terrace
  • Security/Safety
2 bedroom accommodation in Binfield, near Newport From US $103
         

9.6 (5 Reviews)
Cottage
  • Parking
  • Security/Safety
  • Bedding/Linens
A quaint, traditional hut in the heart of the Isle of Wight countryside. From US $152
         

10.0 (29 Reviews)
RV Rental
  • Parking
  • Pet Friendly
  • Security/Safety
1 bedroom accommodation in Wootton Bridge From US $126
         

10.0 (21 Reviews)
RV Rental
  • Parking
  • Pet Friendly
  • Balcony/Terrace
York Street From US $1,342
         

10.0 (8 Reviews)
Ski Chalet
  • Pet Friendly
  • TV
  • Balcony/Terrace
Bell Cottage From US $289
         

10.0 (8 Reviews)
Cottage
  • TV
  • Balcony/Terrace
  • Security/Safety
Pro Tip: Sisterbaycondorentals makes it easy to compare the best listings on Sisterbaycondorentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sisterbaycondorentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osborne House.

Weather in Osborne House

View the weather forecast for Osborne House before booking your Osborne House Vacation Rentals to confirm your best time to go.

December - February
High 43°F       Low 32°F
March - May
High 61°F       Low 36°F
June - August
High 63°F       Low 48°F
September - November
High 58°F       Low 35°F

Osborne House Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Osborne House?
How many vacation rentals are available in Osborne House?

Currently, the total number of properties listed in 2026 is over 609 in the Osborne House area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osborne House.