Photo by Simon Carey (CC BY-SA)

Havenstreet and Ashey holiday rentals

We found 1,311 holiday rentals — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

November 2025

December 2025

Holiday rentals with weekly discounts - Havenstreet and Ashey

Showing deals for:13 Feb - 20 Feb

Exceptional

(22 reviews)

Seaglass, beautiful villa with spectacular sea views over Wheelers Bay & parking

Ventnor, England

9% off

for 7 nights, 1 chalet

AU$213 per night

includes taxes & fees

Exceptional

(82 reviews)

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

Ventnor, ENG

8% off

for 7 nights, 1 home

AU$427 per night

includes taxes & fees

Exceptional

(5 reviews)

Waterfront Cottage Fantastic Sea & River Medina Views From All Aspects

East Cowes, England,

13% off

for 7 nights, 1 cottage

AU$300 per night

includes taxes & fees

Exceptional

(9 reviews)

PRETTY, COSY COTTAGE FOR 2 - 4 NEAR SOUTH COAST, BEAUTIFUL QUIET LOCATION

Ventnor, ISLE OF WIGHT

9% off

for 7 nights, 1 cottage

AU$258 per night

includes taxes & fees

Exceptional

(11 reviews)

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

Ventnor, England

9% off

for 7 nights, 1 apartment

AU$367 per night

includes taxes & fees

Exceptional

(29 reviews)

Spacious Eco friendly house, 5 beds, 4 bath, Fabulous Views, EV Charger

Yarmouth, Isle of Wight.

23% off

for 7 nights, 1 home

AU$498 per night

includes taxes & fees

Exceptional

(88 reviews)

Lovely Cottage With Excellent Sea Views, Minutes From Beaches & Coastal Path

Ventnor, Isle of Wight

22% off

for 7 nights, 1 cottage

AU$247 per night

includes taxes & fees

Exceptional

(18 reviews)

Central Cowes Victorian Cottage. Sunny Garden, 2 baths, Ferry Discount STA.

Cowes, England

8% off

for 7 nights, 1 cottage

AU$354 per night

includes taxes & fees

Exceptional

(112 reviews)

'The Blue House', A cottage with a garden to the beach and amazing sea views.

Cowes, Isle Of Wight

9% off

for 7 nights, 1 home

AU$981 per night

includes taxes & fees

Check in is 4pm. Ring the doorbell for the host.

Exceptional

(36 reviews)

Self catering flat, parking, 4 min walk to beach, 3 min shops. Ferry discount.

Sandown, England

9% off

for 7 nights, 1 apartment

AU$126 per night

includes taxes & fees

Exceptional

(14 reviews)

Jasmine Cottage, 3 Bedroom, Child friendly, 10 mins Walk to Beach, large Garden.

Shanklin, ENG

23% off

for 7 nights, 1 cottage

AU$243 per night

includes taxes & fees

Stunning and unique, the iconic Art Deco House on the Isle of Wight

Exceptional

(49 reviews)

Luxury Art Deco, Award Winning and truly iconic for up to 16 guests

Shanklin, ENG

47% off

for 7 nights, 1 home

AU$1,691 per night

includes taxes & fees

Entrance to Chestnut Mews, Clematis Cottage.

Exceptional

(25 reviews)

Clematis Cottage, Country Setting, 10 min walk to beach, Family Friendly.

Shanklin, ENG

14% off

for 7 nights, 1 cottage

AU$274 per night

includes taxes & fees

Exceptional

(7 reviews)

Lyon Court - The Old Stable - Wooden Cabin (sleeps 3), with Pool

Shanklin

9% off

for 7 nights, 1 cabin

AU$350 per night

includes taxes & fees

Eastern Lee from road with parking for 3 cars.

Exceptional

(20 reviews)

Spacious rural bungalow, disabled friendly, sleeps 2-10, 4 bedrms, 3 bathrooms.

Yarmouth, Isle of Wight

5% off

for 7 nights, 1 home

AU$600 per night

includes taxes & fees

Exceptional

(49 reviews)

Honeysuckle Cottage, Child Friendly, 10 min walk to beach, less to Shops & Park.

Shanklin, England

12% off

for 7 nights, 1 cottage

AU$280 per night

includes taxes & fees

Exceptional

(40 reviews)

Lovely family holiday home in sunny Ventnor

Ventnor, Isle of Wight

9% off

for 7 nights, 1 home

AU$482 per night

includes taxes & fees

Exceptional

(8 reviews)

Elizabeth Apartment- perfectly located with smart TV

Shanklin, Isle of Wight

17% off

for 7 nights, 1 apartment

AU$173 per night

includes taxes & fees

Exceptional

(33 reviews)

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

Sandown, England

8% off

for 7 nights, 1 apartment

AU$206 per night

includes taxes & fees

Exceptional

(14 reviews)

Charming Victorian Cottage In Shanklin Old Village & Dog Friendly

Shanklin, ENG

15% off

for 7 nights, 1 home

AU$785 per night

includes taxes & fees

Exceptional

(9 reviews)

Character Victorian townhouse - conservation area

Portsmouth, England

13% off

for 7 nights, 1 home

AU$402 per night

includes taxes & fees

Exceptional

(9 reviews)

Garden Apartment- perfectly located

Shanklin, Isle of Wight

17% off

for 7 nights, 1 apartment

AU$202 per night

includes taxes & fees

Exceptional

(8 reviews)

Katharine Apartment close to all amenities and beach

Shanklin, Isle of Wight

17% off

for 7 nights, 1 apartment

AU$173 per night

includes taxes & fees

Exceptional

(10 reviews)

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

Shanklin, ENG

36% off

for 7 nights, 1 apartment

AU$189 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Havenstreet and Ashey

Fabulous new kitchen at the center of the house perfect for family and friends

Wonderful home 2min walk to Beach on private beach road, close to West Wittering

Sleeps 13 · 5 bedrooms · 3 bathrooms

Premier Host

Stunning 7 bed on Beach Pool Spa Aga Fire Games room & Exciting update for 2026

Sleeps 15 · 7 bedrooms · 3 bathrooms

Step onto the beach from the Beach House

Premier Host

Sea Front Luxury Beach House, Panoramic Views, Direct Beach access, West Sussex

Sleeps 10 · 4 bedrooms · 3+ bathrooms

Premier Host

Stunning West Wittering Seaside, pet friendly home. 2 mins walk the beach.

Sleeps 7 · 4 bedrooms · 2+ bathrooms

Welcome to Coombe Cottage In West Wittering

Stunning Coastal home only 2min walk to Beach at Wittering, 10min walk to shops

Sleeps 12 · 5 bedrooms · 4 bathrooms

Top rated rentals - Havenstreet and Ashey

Premier Host

Amazing cottage in a great location

We really enjoyed our stay and would throughly recommend it to our family and friends.

Ian H.

Stayed Apr 2025

Premier Host

Ideal location

We found this apartment to be ideal for our visit to the Island. Location was important to us and this matched our needs. Beautifully presented, our host provided everything you might need.It was cosy and comfortable.

James B.

Stayed Aug 2024

Premier Host

Perfect

Quiet, well furnished with all needs met for a very enjoyable stay.We cooked nice meals in the well equipped kitchen, slept well and availed ourselves of the gorgeous surroundings by actually walking.We were well connected to media and were able to be very comfortable.

Lindsay S.

Stayed May 2023

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Havenstreet and Ashey holiday rentals

Holiday rentals with weekly discounts - Havenstreet and Ashey

Image gallery for Seaglass, beautiful villa with spectacular sea views over Wheelers Bay & parking

Seaglass, beautiful villa with spectacular sea views over Wheelers Bay & parking

Find spaces that suit your style

Find the best place to stay - Havenstreet and Ashey

Wonderful home 2min walk to Beach on private beach road, close to West Wittering

Top rated rentals - Havenstreet and Ashey

Amazing cottage in a great location

Peace of mind

More quality time

All the privacy of home

More for less

Explore destinations around Havenstreet and Ashey

Holiday Rental options in Havenstreet and Ashey