Vacation rentals with breakfast in Southampton

Find and book unique accommodations with breakfast on Airbnb

Quick stats about vacation rentals with breakfast included in Southampton

Total vacation rentals
Explore 30 vacation rentals in Southampton
Nightly prices starting at
Southampton vacation rentals start at $354 CAD per night before taxes and fees
Verified guest reviews
Over 600 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities
Vacation rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 of Southampton vacation rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Southampton rentals
4.9 Average rating
Southampton stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated accommodations with breakfast in Southampton

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

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Guest favourite

A charming cottage with a red exterior is surrounded by a lush garden filled with various plants and flowers. A spacious covered porch extends across the front, offering a welcoming entryway. The well-manicured lawn is complemented by vibrant greenery and colorful blooms, creating a pleasant outdoor space.

Cottage in Mount Sinai

The Red Cottage Circa 1936

This cottage is a gem to be found! From the primary room to the charming loft, this cottage can sleep 6! There is a full working kitchen. For those who wish to do exploring, you will be centrally located on LI giving you great ease in using LI rail road (.5 mile) from cottage and Port Jeff Ferry (1mile)from cottage. There is a large fenced in yard with BBQ and outdoor seating if you wish to dine in. Dogs are allowed w/prior notice and a $65 pet fee per dog. You won’t beat this value reserve now.

LocationFamilyHospitality

4.8 out of 5 average rating, 557 reviews

Superhost

The exterior of a spacious home is showcased against a clear blue sky. Lush green grass and neatly trimmed shrubs surround the house, which features a blend of shingle and clapboard siding. Large windows and a welcoming front porch can be seen on the facade.

Home in Remsenburg - Speonk

Luxury Hampton Home Near Bay 4 beds 4 Baths

Located in the quiet hamlet of Remsenburg, 70 miles East of NYC, four bedroom home has it all. Situated on a quiet park like setting 600’ from the waters edge. Take a short walk to the water or longer walks to view historical estates. Two miles from Westhampton or Eastport Main Streets where you will find eateries and shops. Open floor plan so you can socialize while preparing dinner. Resort style backyard with huge heated pool, swim spa jacuzzi, peloton bike, game room, in and outdoor dining.

LocationCleanlinessAmenities

Guest favourite

A bright and open living area features a large sectional sofa with colorful accent pillows and light-colored armchairs. A dining area with modern chairs is visible in the background, while floor-to-ceiling windows provide a view of the outdoor pool and greenery.

Home in East Hampton

Chic, Modern, Family-Friendly Home in East Hampton

This clean, beautiful, well appointed home is the perfect place for your summer (or winter) getaway! With updated appliances and designer furniture, this chic getaway is both fun and sophisticated. Whether you're a family or a small group of friends, you will make wonderful memories swimming in the heated gunite pool, playing badminton in the yard, grilling on the deck or sipping wine on the balcony. Close to the village, and both bay and ocean beaches! Rental Registry Certificate: RR-25-371

LocationFamilyCheck-in

5.0 out of 5 average rating, 17 reviews

Top guest favourite

A decorative mailbox featuring a starry night design stands at the entrance, with the number 33 visibly displayed. Bright orange flowers and lush green foliage surround the mailbox, while the cottage is partially visible in the background, framed by a white fence.

Cottage in North Fork

A Cheerful 2 - Bedroom Cottage

The cottage is the perfect resting spot for travelers. While staying here you can enjoy nature, farms, vinyards, beaches, golfing, and local attractions. We are conveniently located between the North and South Forks of Long Island. We are in walking distance to the Hampton's Jitney. A 2 min drive to the LIE. And just a 40 min drive to the Orient Pt Ferry. We are 30 mins to The Hamptons, and 5 mins to the LIRR. Most importantly we can assure your stay with us will be, peaceful and comfortable.

FamilyLocationDecor

4.98 out of 5 average rating, 51 reviews

Top guest favourite

An airy kitchen features white cabinetry and a large island with seating. Modern appliances are included, and a glass atrium provides sunlight. Potted greenery adds a touch of nature, and a view of the outdoor pool is available through expansive glass windows.

Home in Sag Harbor

Beautiful 4/bedroom Sag Harbor Home /Heated pool

Spacious 4 bedroom, 3 1/2 bathrooms,Heated pool with outdoor shower.Located on one acre, in beautiful upscale neighborhood,at end of quiet cul-de-sac street. Large 65"TV in huge cathedral ceiling main living room . 65'screen TV in large separate den,with treadmill. King size bed on 1st floor bedroom with 2 beds next door New large Spa bathroom on 1st floor. King size master bedroom 2nd floor,55"TV,with en-suite 2 beds in add bedroom, with en-suite bath July and August are Monthly Rentals

FamilyLocationAccuracy

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Home in Mastic

Modern Hamptons Home

Escape to a beautifully renovated Hamptons retreat designed for comfort, privacy, and effortless outdoor living. Enjoy a spacious deck and private fenced backyard featuring a unique outdoor lounge, BBQ grill, fire pit, and refreshing outdoor shower. Inside, bright and stylish spaces offer all the comforts of home. Perfect for relaxing, dining outdoors, and creating memorable moments with family and friends, all while being conveniently located near beaches, restaurants, shopping, and local.

LocationValueKitchen

4.99 out of 5 average rating, 67 reviews

Top guest favourite

A spacious bedroom features an elegantly designed headboard with a floral pattern. The walls are adorned with a soft blue and white mural, complemented by natural light filtering through a window. A tall mirror reflects the room, enhancing the sense of openness.

Guesthouse in Port Jefferson

The Buccaneer Suite ~ Your Private Seaside Escape

Come be enchanted with The Buccaneer, a private, luxurious yet charming two-bedroom duplex suite nestled within Falaena House Inn - our historic, eco-conscious retreat. Blending coastal elegance with maritime spirit, The Buccaneer offers a rare sense of seclusion while placing you a mere two-minute stroll to the beach, local shops & coastal eateries. At Falaena House Inn, we care deeply for the land, the sea, and you! We welcome you home like a captain to port (adult-only, no-pets).

FamilyLocationCleanliness

5.0 out of 5 average rating, 23 reviews

Guest favourite

The cottage exterior features a welcoming front porch, framed by large glass windows that brighten the space. Lush greenery surrounds the entrance, and a set of steps leads to the doorway. Natural light highlights the inviting Cape Cod design.

Cottage in Southampton

Summer Cottage

Cottage in Roses Groves, Southampton, NY. Great location to avoid traffic on 27. Cottage has access to a private beach on the Peconic Bay (5 min walk). 15 min drive to ocean beaches in Southampton, and Southampton village. 10 min drive to Watermill, 20 min to Sag Harbor and BH. A farm and a deli are less than a mile away. Two restaurants nearby Perfect for artists, ocean lovers, book lovers and families. A/C in living room and bedrooms. Located on a quiet street, very relaxing

FamilyValueQuiet

4.79 out of 5 average rating, 28 reviews

Guest favourite

A bright living area features a light-colored sectional sofa adorned with decorative cushions. A wooden coffee table is positioned in front, with two dark wooden chairs beside it. Natural light filters through the large windows, highlighting the textured walls and elegant decor.

Home in East Hampton

Bright and airy East Hampton cottage

Charming East Hampton cottage with heated saltwater pool and pool/guest house. This recently renovated 2000 square foot home is the quintessential Hamptons cottage The location is within walking distance to the town of East Hampton and the train station and there are several ocean beaches within 2 miles. This is the perfect house for a family beach vacation, or a get together with friends. No large groups or parties please. We love our house and our quiet neighborhood!

LocationFamilyBiking

5.0 out of 5 average rating, 19 reviews

Guest favourite

A sunlit seating area features a wooden bench adorned with colorful cushions. A round area rug is centered on the terracotta floor. A large mirror reflects light, while a doorway leads to a well-lit bedroom, accented by a photo and a decorative tub nearby.

Apartment in Sag Harbor

Artists pet friendly apartment and cabin, sauna.

Full apartment with full bathroom 10 minutes to all Hampton towns. Quiet property Walking distance to free SUP boards and canoes and only 2 minute drive to a dog friendly beaches. Extra bedroom is a Cabin in the middle of the property and was a recording studio, now has queen bed, wifi, fridge, micro wave, heat and AC, TV and DVD player but no bathroom. You have your own parking spots, entrance and outdoor dining area and outdoor shower.

LocationBeachIndoor spaces

4.84 out of 5 average rating, 25 reviews

Top guest favourite

A vibrant garden area is depicted, featuring a variety of blooming flowers in decorative pots. Greenery surrounds the space, with bushes adorned with purple blossoms. A wooden deck offers a view over the lush, well-maintained landscape.

Guesthouse in Brookhaven

The Unhampton

This Brookhaven Hamlet detached space (totally separate) is for people who love nature and preserved quiet spaces. Fire Island is a ferry ride away, Manhattan is one hour by train and the Hamptons are a 25 minute ride.15 minutes from the restaurants and coffee shops in Patchogue and just a couple of minutes from Bellport Village. Centrally located and truly peaceful!

ValueLocationCheckout

4.97 out of 5 average rating, 242 reviews

Top guest favourite

A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.

Home in North Fork

Secluded Farmhouse - Studio Apartment Style Unit

Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

FamilyLocationBathroom

4.96 out of 5 average rating, 222 reviews