Holiday rentals in Southampton

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Top-rated holiday rentals in Southampton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A vibrant green lawn stretches towards the water, framed by lush trees. A tall palm tree towers above, while the shoreline and ocean are visible in the background under a clear blue sky scattered with fluffy white clouds.
Home in Southampton
4.97 out of 5 average rating, 228 reviews

Sea Breeze Mews on the Little Sound

Cozy & compact, this delightful 1 bedroom/2 story waterfront hideaway affords a panoramic view of the Little & Great Sounds. On the water (walk across the lawn and jump in) with a large dock suitable for swimming, snorkeling & spectacular sunsets. "Sea Breeze Mews" is only a 10 minute walk to picturesque Church Bay beach & a short bus ride to all the magnificent South Shore Beaches. Restaurants and award winning Golf courses are only a few minutes away. Public transportation right outside gate.

Top guest favourite
A clear view of the glistening pool is presented, surrounded by lounge chairs and colorful umbrellas. The expansive lawn leads to scenic ocean views, framed by coastal vegetation and nearby homes under a blue sky.
Flat in Southampton
5 out of 5 average rating, 84 reviews

'Ripple Waters' - More for Les$ 1 Bdrm Pool House

Guests can choose from the ONE BEDROOM POOL HOUSE (spacious living room) and/or Studio B (new listing). Relax and enjoy 'Ripple Waters' home away from home. This unique and tranquil 'more for le$$' getaway offers a peaceful, relaxing and rejuvenating experience for couples! Wade in the 20' by 40' glistening pool or sunbathe on the spacious upper patio deck. Listen to the melodious, chirping birds as you read a book or gaze at the beautiful views of South Shore. Sit back, relax and enjoy!

Top guest favourite
A spacious queen-size bed with a woven rattan headboard is featured in a bright bedroom. Soft, neutral bedding complements the design. Side tables with lamps are placed beside the bed, and a sliding glass door opens to a lush outdoor area.
Guest suite in Southampton
4.96 out of 5 average rating, 395 reviews

PANATOLA STUDIO- Breathtaking Views Close to Beach

Panatola Studio is your own charming home away form home. Consistently been the most highly recommended vacation rental in beautiful Bermuda! Located in a desirable neighbourhood of Southampton with a breathtaking view! Conveniently located within walking distance to Horseshoe Bay beach, the lighthouse, a golf course and wonderful restaurants. Fully furnished with all the amenities you need for a relaxing vacation. Mini Electric car charger available! *Another studio above for other 2 guests.

Guest favourite
A private patio area features a dining table surrounded by white chairs, set against a backdrop of lush greenery and colorful homes. A light-patterned rug adorns the tiled floor, while the bright sky is dotted with fluffy clouds.
Home in Southampton
4.96 out of 5 average rating, 56 reviews

The Bungalow at Cedar Brae - Cozy and Bright

The Bungalow at Cedar Brae is a 1-bedroom, 1-bath home located on our quiet Cedar Brae property which is just a 10-minute scooter ride to Horseshoe Bay and a 3-minute walk to the closest bus stop. This is a place for couples and small families to rest and relax. We hope that you appreciate every part of your stay; from sipping a cup of coffee on the patio to enjoying a nice meal at the outdoor dining table under a clear blue sky. Check out our Instagram for a better view: @thebermudabungalow

Guest favourite
A spacious studio layout features a king-size bed with an elegant headboard and soft gray bedding. A comfortable sofa is positioned adjacent to a dark wood nightstand. Art pieces and lamps provide ambient lighting, while windows allow natural light into the room.
Flat in Southampton
4.9 out of 5 average rating, 220 reviews

SOUTH SHORE GEM (Beach, Electric Car Charger)

Located above Church Bay on beautiful South Shore (15 miles of the most beautiful coastline) sits a Modern, delightful studio full of luxuries. Features A/C, king size TEMPURPEDIC bed, Queen sofa-bed, 55" TV, WI-FI(fiber), KOHLER bubble-massage tub, full kitchen, granite countertops, washer/dryer, private patio, EV Car Charge Point/Outlets, Electric Fireplace, partial ocean view and in the unlikely event of power loss - full solar/battery backup and full generator backup if all else fails! .

Top guest favourite
The pool area of Sea Glass Cottage features a sparkling blue pool surrounded by a spacious deck. A lookout tower is positioned nearby, with shaded seating areas under large umbrellas. Lush palm trees and greenery frame the scene against a bright blue sky.
Guest house in Warwick Parish
4.95 out of 5 average rating, 179 reviews

Sea Glass Cottage with EV charging station

Your own private pool house + tower on a lush 5-acre estate Sea Glass Cottage—ranked the #6 best Airbnb in Bermuda by Condé Nast, and the #1 spot that’s not right on the water Spacious 1,400 sq. ft. pool house: Open-plan living + dining with exposed beams, soaring ceilings, separate bedroom, with AC + comfy queen bed Well stocked kitchen with full-sized fridge, BBQ Updated bathroom, walk-in shower. TV, washer/dryer, ceiling fans, dedicated Wi-Fi The only thing you’ll share? The gorgeous pool.

Guest favourite
An aerial view reveals a well-maintained cottage surrounded by lush tropical gardens. A private pool is centrally located, featuring inviting turquoise waters. Lounge chairs are positioned around the pool deck, providing a tranquil space for relaxation among the greenery.
Cottage in Warwick
4.89 out of 5 average rating, 175 reviews

Natalia Pool Cottage

This is great for a weekend getaway or even a week or two!! With quick flights from NYC and Boston and East Coast No children under 18 years old and those who cannot swim. You can now rent a TWIZY from currentvehicles !! TWIZY – a four wheeled, two seater, battery powered little car – contact them for details and to book. Drive all day – charge it overnight at Natalia!! Please note there is no Available Parking - other than for Scooters or Electric Vehicles. I.E. No Car Parking.

Top guest favourite
A cozy seating area features a blue sectional sofa adorned with striped and text-patterned cushions. Above, framed artwork of a sea turtle is displayed, complemented by a light fixture and a round wall clock. A media console below holds books and decorative items.
Guest house in Southampton
4.99 out of 5 average rating, 152 reviews

The Pool House at 'Lemon Tart'

The Pool House at 'Lemon Tart' is the perfect escape in paradise! Set in a private garden near the sea and pink sand beaches, this delightful guest rental is in an excellent location to begin exploring beautiful Bermuda. https://www.gov.bm/coronavirus-travellers-visitors Tourism info, bus route (see # 7) https://www.gotobermuda.com Ask questions on ‘Bermuda Bound’ fb page Grocery delivery: www.dropit.bm Take-out App: Sargasso Public transport app: PinknBlue Taxi app: Hitch

Guest favourite
Flat in Warwick
4.9 out of 5 average rating, 197 reviews

Private apt walk to Bermuda's Best Beaches

Private studio in a quiet residential neighbourhood across from the entrance to Warwick Long Bay Beach. Full kitchen, private patio, and garden. Walking distance to South Shore beaches, dunes, and trails, including Horseshoe Bay. Note: Bermuda is hilly. All South Shore beaches are accessed via steep hills, and there is a steep hill in and out of the neighbourhood. Not an easy walk to a grocery store. Ideal for guests comfortable with hills and a quiet setting.

Guest favourite
A modern living area features a sectional sofa with decorative pillows and a matching ottoman. Wall-mounted shelves display minimal decor. A television is positioned against the wall, complemented by a cabinet. Natural light enters through the window, partially covered by dark curtains.
Flat in Southampton Parish
5 out of 5 average rating, 32 reviews

Hole in One

Welcome to Hole in One, a modern and newly built 2-bedroom apartment with 1.5 baths! Situated just 200 yards from the prestigious PGA Port Royal Golf Course, this is a golfer's paradise. With the beach, restaurants, a playground, gas station, grocery store, boat marina, and the charming smallest drawbridge attraction within a mile, you're in the perfect location. Transport is a 10-minute walk to the nearest Ferry and the Bus stop is outside of the unit.

Top guest favourite
A bright living area showcases a comfortable seating arrangement with a beige sofa and armchair. A dining table for four is positioned near the window, framed by patterned curtains. Natural light floods the space, accentuating the polished wooden floor.
Flat in Southampton Parish
4.99 out of 5 average rating, 113 reviews

Relaxed Bermuda Cottage - 1 bedroom, sleeps 2

Cottage is a lovely 1 bedroom apartment with full kitchen, bathroom and living / dining room as well as a private patio area. Nearest beach is a 5-10 minute walk and the bus stop a similar distance. 2 restaurants are within walking distance (The Reefs and Henry VIII). Personal laundry also by arrangement with host in next door house. We have a charging station for the new Current Vehicle - TWIZY. For details see Current Vehicles website.

Top guest favourite
Two Adirondack chairs face the ocean, positioned on lush green grass. The vibrant blue water stretches into the horizon under a clear sky, creating a serene and inviting outdoor space.
Home in Bermuda
4.99 out of 5 average rating, 293 reviews

Contemporary Oceanfront Apartment with shared pool

A contemporary oceanfront apartment located at the end of a quiet lane on the south shore between Whale Bay and Church Bay. Ideal for those looking to relax, with great ocean views from every room We also have a 3 Bed Contemporary Oceanfront Villa with private horizon pool approximately a mile down the road perfect for larger groups and family gatherings! Can be booked together for groups up to 8! https://www.airbnb.com/rooms/23767162

Popular amenities for Southampton holiday rentals

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