Havenstreet and Ashey holiday homes

We found 1,562 holiday rentals — enter your dates for availability
Discover a selection of 22 cottages and other holiday rentals in Havenstreet and Ashey that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the amenities that you expect and more, which might include a garden and pool. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Havenstreet and Ashey

Showing deals for:13 Nov - 20 Nov

Private kitchen
Interior
Exterior
Interior
Exceptional
(26 reviews)

2 Bedroom Chalet With Private Decking

Sandown

9% off
NZ$1,618
for 7 nights, 1 chalet
NZ$231 per night
includes taxes & fees
2 Bedroom Chalet With Private Decking
Living area
Exterior
Dining
Exterior
Exceptional
(5 reviews)

Cosy converted barn in rural location with views of the surrounding countryside.

Newport

9% off
NZ$1,913
for 7 nights, 1 cottage
NZ$273 per night
includes taxes & fees
Cosy converted barn in rural location with views of the surrounding countryside.
Room
Interior
Living area
Dining
Exceptional
(48 reviews)

Modern House with amazing views sleeps 10

Cowes

8% off
NZ$10,061
for 7 nights, 1 home
NZ$1,437 per night
includes taxes & fees
Modern House with amazing views sleeps 10
Private kitchen
Dining
Outdoor dining
Interior
Exceptional
(9 reviews)

Spacious semi-detached Southsea House

Portsmouth

13% off
NZ$3,549
for 7 nights, 1 home
NZ$507 per night
includes taxes & fees
Spacious semi-detached Southsea House
Looking from the Garden Room downstairs, uninterrupted vies out to sea
Magnificent bed from Paris 1930s
Wonderful gardens to relax in during the warmer months
The upstairs "Gallery" joining 3 of the bedrooms
Exceptional
(49 reviews)

Luxury, award winning Art Deco house for special holidays and family events

Shanklin

9% off
NZ$23,047
for 7 nights, 1 home
NZ$3,292 per night
includes taxes & fees
Luxury, award winning Art Deco house for special holidays and family events
Living area
Dining
Private kitchen
Dining
Exceptional
(11 reviews)

Superb Sea View, all amenities in walking distance, new renovation

Ventnor

38% off
NZ$2,120
for 7 nights, 1 cabin
NZ$303 per night
includes taxes & fees
Superb Sea View, all amenities in walking distance, new renovation
Dining
Exterior detail
Living area
Private kitchen
Exceptional
(10 reviews)

Bermuda House with parking, good sea view and minutes from beach and shops

Ventnor

23% off
NZ$2,251
for 7 nights, 1 home
NZ$322 per night
includes taxes & fees
Bermuda House with parking, good sea view and minutes from beach and shops
Living room to sunny deck
Day bed
Property grounds
Cosy by night
Exceptional
(83 reviews)

Luxury, Stylish Home, With Garden, Sea Views and Parking.

Ventnor

9% off
NZ$3,530
for 7 nights, 1 home
NZ$504 per night
includes taxes & fees
Luxury, Stylish Home, With Garden, Sea Views and Parking.
Garden furniture
Caribbean restaurant, 3 mins walk away.
King sized bed. Blanket box has throws and a large bedspead in.
43” smart tv and storage. Patio door to courtyard garden.
Exceptional
(42 reviews)

Self catering flat, parking, 4 min walk beach, 3 min shops. Car ferry discount.

Sandown

9% off
NZ$1,014
for 7 nights, 1 apartment
NZ$145 per night
includes taxes & fees
Self catering flat, parking, 4 min walk beach, 3 min shops. Car ferry discount.
Private kitchen
Interior
Dining
Outdoor dining
Exceptional
(42 reviews)

Lovely family holiday home in sunny Ventnor

Ventnor

9% off
NZ$4,653
for 7 nights, 1 home
NZ$665 per night
includes taxes & fees
Lovely family holiday home in sunny Ventnor
Living area
Private kitchen
Beach
Room
Exceptional
(24 reviews)

Luxury Three Bed Apartment with Balcony and Seaviews

Ventnor

9% off
NZ$6,382
for 7 nights, 1 apartment
NZ$912 per night
includes taxes & fees
Luxury Three Bed Apartment with Balcony and Seaviews
Property grounds
Shanklins Beach Huts (Small hope Beach)
Children’s area
Jasmine master bedroom
Exceptional
(15 reviews)

Jasmine Cottage, 3 Bedroom, family friendly, 10 min Walk to Beach, large Garden.

Shanklin

20% off
NZ$1,920
for 7 nights, 1 cottage
NZ$274 per night
includes taxes & fees
Jasmine Cottage, 3 Bedroom, family friendly, 10 min Walk to Beach, large Garden.
Living area
Dining
Private kitchen
Room
Exceptional
(12 reviews)

Luxury ground floor one bedroom apartment yards from the beach and High Street

Ventnor

9% off
NZ$1,517
for 7 nights, 1 apartment
NZ$217 per night
includes taxes & fees
Luxury ground floor one bedroom apartment yards from the beach and High Street
Room
Front terrace leading of dining/kitchen area
Living area
Your apartment at the front of the complex
Exceptional
(159 reviews)

Luxury Cowes waterfront apartment with exceptional Marina and Solent Sea Views

Cowes

8% off
NZ$2,877
for 7 nights, 1 apartment
NZ$411 per night
includes taxes & fees
Luxury Cowes waterfront apartment with exceptional Marina and Solent Sea Views
Cottage kitchen with pine extending table & Bentwood chairs
Terrace/patio
Living area
Private kitchen
Exceptional
(85 reviews)

Edge of Old Village, close to shops, park and beach; ferry discounts

Shanklin

5% off
NZ$3,310
for 7 nights, 1 cottage
NZ$473 per night
includes taxes & fees
Edge of Old Village, close to shops, park and beach; ferry discounts
Interior
Sandown
Master bedroom
Hall
Exceptional
(36 reviews)

Seaways, in Sandown,for a great relaxing holiday, Family friendly, free parking

Sandown

8% off
NZ$1,746
for 7 nights, 1 apartment
NZ$249 per night
includes taxes & fees
Seaways, in Sandown,for a great relaxing holiday, Family friendly, free parking
Welcome to The Seascape.
Bedroom with ensuite
Enjoy the 80m landscape garden that sweeps down to the cliff edge
The Private Garden, enjoy 80m of landscape gardens
Exceptional
(15 reviews)

The Seascape, luxury 3 bed apartment with panoramic sea views, garden & hot tub

Shanklin

36% off
NZ$2,620
for 7 nights, 1 apartment
NZ$374 per night
includes taxes & fees
The Seascape, luxury 3 bed apartment with panoramic sea views, garden & hot tub
Master Bedroom
Terrace
Welcome to Dove Court!
Living space
Exceptional
(5 reviews)

Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging

Shanklin

36% off
NZ$1,515
for 7 nights, 1 apartment
NZ$216 per night
includes taxes & fees
Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging
Open Plan Living Space Kitchen, Dining, Lounge
Welcome to Dove Court!
Terrace
Kitchen/Dining
Exceptional
(8 reviews)

Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging

Shanklin

35% off
NZ$1,274
for 7 nights, 1 apartment
NZ$182 per night
includes taxes & fees
Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging
Private kitchen
Outside Terrace.
Welcome to Dove Court!
Views over Shanklin Town.
Exceptional
(9 reviews)

Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging

Shanklin

36% off
NZ$1,515
for 7 nights, 1 apartment
NZ$216 per night
includes taxes & fees
Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging
Master Bedroom
Welcome to Dove Court!
Entrance Hall.
Kitchen
Exceptional
(10 reviews)

Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging

Shanklin

36% off
NZ$1,515
for 7 nights, 1 apartment
NZ$216 per night
includes taxes & fees
Vectis Holiday Homes, Modern, spacious apartment, great location, EV Charging
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    Enjoy full kitchens, laundry, pools, gardens and more
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Find the perfect holiday rental for your Havenstreet and Ashey getaway

Learn about the unique charm of Havenstreet and Ashey with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Havenstreet and Ashey

Do you want to discover attractions to see during your stay? Venture out of your cosy holiday rental and check out everything that Havenstreet and Ashey has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Isle of Wight Zoo (4 mi / 6.4 km)
  • Clarence Pier (7.4 mi / 12 km)
  • Blackgang Chine (9.1 mi / 14.6 km)
  • The Needles Landmark Attraction (15.9 mi / 25.6 km)
  • The Quays (16.4 mi / 26.4 km)
  • Garlic Farm (1.5 mi / 2.5 km)

Exploring the natural landscape of Havenstreet and Ashey

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Havenstreet and Ashey is a great spot to appreciate mother nature. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • New Forest National Park (21.4 mi / 34.4 km)
  • Isle Of Wight Coastal Footpath (3.1 mi / 4.9 km)
  • Ryde Beach (3.2 mi / 5.2 km)
  • Seaclose Park (3.6 mi / 5.7 km)
  • Sandown Beach (4 mi / 6.4 km)
  • Yaverland Beach (4.2 mi / 6.8 km)

Transport options to and around Havenstreet and Ashey

Fly into Southampton (SOU), the closest airport, located 18.5 mi (29.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Bournemouth (BOH-Bournemouth Intl.), which is 27.9 mi (44.9 km) away.

Frequently asked questions

Can I find a holiday rental in Havenstreet and Ashey?
Yes, there are holiday rentals in Havenstreet and Ashey close to Isle of Wight Steam Railway, or you can select a more secluded option if you're looking for a relaxing stay.
How many holiday rentals are there in Havenstreet and Ashey?
With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Havenstreet and Ashey stay.
What can I see and do in Havenstreet and Ashey?
Isle of Wight Area of Outstanding Natural Beauty and Robin Hill Country Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Robin Hill. In the wider area, you'll find Isle of Wight Steam Railway and Southampton Cruise Terminal.
What are holiday rentals like in Havenstreet and Ashey?
Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Havenstreet and Ashey. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family getaway.