Holiday rentals in Weymouth and Portland District

Blue Skies Retreat,Modern house Chesil Beach

Modern semi-detached house located two minutes walk from Portland Marina and Chesil beach. Perfectly situated for divers, walkers sailors and anyone who pursues water based activities. Pubs restaurants and takeaways within walking distance of the house. Private parking situated at the front of the property. This house has a modern contemporary interior with two double bedrooms. One of these with twin beds. Enclosed rear garden with patio and seating area perfect for watching the Chesil sunset.

Islands Wrest (The Galleon Rm). Pet friendly.

Nautical galleon themed room with own entrance, kitchen & shower room this your own space within owner occupied property. Explore Portland, an Island that features breathtaking views, beautiful walks. Castles, 3 lighthouses. Chesil beach. a Museum, rock climbing, wildlife, water sports. History of smugglers & pirates explore Church Ope Cove. 20 min on bus to Weymouth for more seaside fun! Set centrally on the Jurassic coast. This is a real hidden gem. Not suitable for infants (Adults only)

Flat One The Beaches

New for 2026 parking permit for Zone F on street parking The apartment is in a central position & can be noisy in the evenings especially at the weekends Recently converted Grade II listed property on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.

Seaside studio cabin minutes from 'secret' beach

Tucked away up an unmade track & five minutes walk from a 'secret' local beach; Cove Cabin is a compact, stylish, private space; perfect for a couple or two companions. On the doorstep of lesser known beaches & gardens but not far from Weymouth's bustling scenic harbour & golden sands. Ideal stop off whilst walking the SW Coast Path. The perfect area for watersports, wild swimming, walking, mooching around the harbour & locality, sampling the local seafood & eateries & just simply relaxing.

Townhouse Flat

A lovely one bed first floor flat within family home. The flat sleeps 4, max 5 with z bed. The flat is self-contained, but is accessed via the family home front door, hallway and stairs. The flat is on the first floor of a period townhouse on Dorchester Road, and is close to local amenities (Tesco Express, pub, Post Office and chip shop). The beach is a 10 min walk away and the town centre is a 20 min walk. Free on street parking is available. See additional charges for Z bed hire.

Newly built self contained Annex in Weymouth

A new purpose built self-contained annex, located in one of Weymouth's most prestigious and quiet locations. Situated a few minutes walk from a local beach and with just a 10 minute walk to Weymouth harbour. The property is thoughtfully furnished to provide a comfortable experience. A large Juliet balcony and plenty of windows ensure a light and airy ambience. Private gated off road parking with security cameras leads to a rear self contained outdoor patio area and the main entrance.

Beachside View

Enjoy easy access both beach and town centre from this beachfront couples' retreat. This top floor (3rd floor) flat has panoramic views across the bay and there's even a telescope. This apartment is right next to a M&S food hall and within 100m of a fish n chip shop, a Chinese takeaway, a traditional pub and several bars and restaurants. There is a king size bed in the bedroom and a sofa that pulls out into a bed in the lounge. Access to the bathroom is through the bedroom.

Breeze - White Stones Studios

Come and enjoy unique contemporary eco-friendly accommodation set in peaceful and creative surroundings at the heart of Easton, Portland, on the tip of The Jurassic coast. Located to the rear of White Stones Art Cafe's secluded and tranquil gardens there are three holiday studios available, each sat nestled together in peaceful surroundings. Breeze is one of our three bespoke holiday studios, finished to a high standard and providing a contemporary holiday experience.

The Palms at No10 - Spacious and Family Friendly

Welcome to the Palms at No10! Unwind in this stylish and beautifully appointed home for your stay on the Jurassic Coast. The property offers ample space for 6 guests across three stunningly finished bedrooms, and our outdoor terrace provides al fresco to unwind after a day exploring everything Dorset has to offer. The Palms is perfectly located for a coastal getaway, with both the town centre just a short 20 minute walk away and the seaside only a stones throw away.

The Penthouse (Small but mighty)

Enjoy a stylish experience at this centrally-located place on the Isle of Portland. So many places to visit and all within a stones throw away from our newly refurbished Penthouse. Guest access- just off the road down a private drive with one parking space directly outside. The space- One small but stylish room with a double bed and luxury bedding. Mini fridge and kettle. En-suite modern bathroom, towels included. Check-in from 16:00pm Check out before 10:00am

Quirky 2 bed holiday home with hot tub and sauna.

Newly built 2 bedroom cottage with hot tub and sauna located in Easton on Portland in Dorset. This unique home is built in Portland stone and has a ground floor outdoor space with patio and outdoor oven area as well as having an upstairs outdoor mezzanine area with bi-folding doors. The main living space that includes a 90” smart television. Both bedrooms have super king beds and are en-suite with doors to outside access and large smart tv screens

"The Escape" 2 bed property 100m from beach ..

Location, Location, Location! The Escape is nestled right in the heart of Weymouth, a few minutes walk from the beach, shops, pubs and restaurants. This beautiful refurbished 2 bedroom 2 bath maisonette can sleep up to 5 comfortably, perfect for a family holiday or couple/s enjoying a short break . Bedroom 2, has a King size bed and a single bed. Nearby carparks. A permit can be arranged at extra cost. Parking is not guaranteed.