It’s only September, but you know what’s coming. Some people embrace winter — they wax their skis, swaddle in wool, and insist they actually enjoy short, gray days. And then there are the rest of us, who know ourselves well enough to admit that by January we’ll be miserable. The light therapy lamp won’t be cutting it, our boots will always be wet, and every time we step outside, we’ll swear it’s the coldest we’ve ever felt.
If you fall into that camp, don’t let a warm-weather getaway be an afterthought. By the time December rolls around, all the best Airbnbs in sunny places will already be booked. Instead, plan ahead and give yourself something to look forward to — a midwinter escape where “layering up” means a billowing kaftan and the only hazardous ice is the oversized hipster cube in your cocktail. And luckily you don’t have to go far. From Mexico to California to Puerto Rico, these coastal Airbnbs are worth bookmarking now, so when the dark days hit, your escape plan is already in place.
We hope you love the spaces and stays we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Bohemian beachfront home with deck and whale watching in Ventura, California
See more photosBlending traditional and modern design, this house features oceanfront views and contemporary amenities from a superb location at Faria Beach. Get cozy inside this dreamy space and gaze out the large windows at the water, or watch the surf and look for wildlife like whales while getting some fresh air on the spacious private deck. The “beachy” feeling space emits a sense of relaxation and eclecticism, with nautical decor elements like seashells and light blue and whitewashed walls.
The living, dining and kitchen areas are oceanfront — meaning idyllic views. Make a meal in the fully equipped kitchen with a dishwasher and subzero refrigerator. There are two main bedrooms with clean and comfortable queen beds on the main level, and the sleeping space is in the family-style living room, with two twin beds and a couch, TV, and laundry machine.
Six guests, three bedrooms
Price: $930 per night
The ultimate beach house in Port Aransas in Padre Island, Texas
Padre Island, also known as North Padre, is surprise, surprise, north of the laid-back South Padre Island near Brownsville, Texas. To complicate this further, I’m adding Mustang Island to the mix and suggest staying in Port Aransas. Mustang Island is accessible by a ferry from the north or a bridge from the top of Padre. The entire region deserves exploration, so base yourself in Port Aransas, bring or hire a vehicle, and allow yourself time to enjoy the miles of sandy beaches and the climate of the tropical southern tip of Texas.
One to bookmark, this is the ultimate beach house. You’ll be set up for success with a stay here as the hosts have thought of everything. Entertainment is sorted with the game room with arcade machines, outdoor games for the yard, and a private heated pool with an outdoor shower. There’s a built-in EV charger, complimentary beach gear, and the rental comes with a six-seater golf cart for zooming around the island.
12 guests, four bedrooms
Price: $750 per night
Dream 3-bedroom villa with infinity pool in Todos Santos, Mexico
An hour north of Cabo but a world away in atmosphere, Todos Santos skips the resort sprawl in favor of cobblestone streets, colorful art galleries, and a distinctly bohemian pace. Winter brings clean Pacific swells that keep surfers paddling out at Playa Cerritos, while in town you can wander between craft coffee shops, taco stands, and small studios before catching one of Baja’s signature fiery sunsets.
Staying in Todos Santos usually means choosing between tucked-away casitas near the town’s galleries or modern villas with views of the Pacific. This three-bedroom home sits right at that intersection — close to shops and restaurants but perched above an arroyo with sweeping mountain and ocean views. The design blends contemporary lines with hacienda-style details, and each bedroom opens to the outdoors. A chef’s kitchen, shaded dining patio, and a lap pool for cooling off make it an easy base for exploring town or the beaches just down the road.
Six guests, three bedrooms
Price: $615 per night
Planning a winter vacation? Check out Matador’s winter accommodations guides:
- The Best Ski-In/Ski-Out Airbnbs in Park City Minutes From the Slopes
- Get Cozy in These 10 Lake Tahoe Cabins and Mountain Homes on Airbnb
- Stunning Aspen Airbnbs to Take in the Country’s Most Glamorous Mountain Town
- Surrey’s Cottage Core Airbnbs Help You Live Out ‘The Holiday’ IRL
- The most sought-after ski-in/Ski-out Airbnbs in Big Sky Montana for groups and families
- The 63 Most Exciting New Hotels of 2024
Cliff House with stunning pool and waterfall view in Maui, Hawai’i
Winter in Maui means peak humpback whale season. Every year, thousands of whales migrate from Alaska to the warm Hawaiian waters to give birth and raise calves, and sightings are almost guaranteed from December through April. The beaches around Kāʻanapali and Wailea are perfect for spotting spouts offshore, and guided whale-watching tours get you even closer to the action. Add in warm ocean temps for snorkeling, lush hikes through ‘Iao Valley, and the Road to Hana’s waterfalls — Maui delivers both adventure and relaxation in the middle of winter.
This epic cliff house, 300 feet above the ocean, encapsulates everything great about a stay on Maui. The ocean is right there, you have a private pool and hot tub, and you can relax over cocktails while gazing at the Hanehoi Waterfall. Hana is visible from the home, as is the north coast of Maui. Relax over a book next to the 10-foot marble fireplace, though focusing on the pages may prove to be a struggle with the scenery of paradise in the background. You’ll never have a better view from a hot tub, this we can guarantee. For more stunning Airbnbs on the island, check out Matador’s wider selection of Maui Airbnbs and other great finds on Hawai’i’s beaches.
Three guests, one bedroom
Price: $481 per night
Beachfront 2-bedroom apartment with pool on Dogman’s Beach in Rincón, Puerto Rico
On Puerto Rico’s west coast, Rincón earns its reputation as the “surfing capital of the Caribbean.” From December to March, the waves are at their best, drawing surfers from around the globe. But it’s not just for board riders: the town is famous for golden sunsets, casual beach bars, and whale-watching along the coast. No passport needed for US travelers, and with warm evenings perfect for outdoor dining, Rincón offers an easy Caribbean getaway during the colder months back home.
In Rincón, many Airbnbs line the town’s surf breaks, ranging from simple beach apartments to larger villas with shared pools. This two-bedroom unit sits right on Dogman’s Beach, one of the area’s most famous stretches of sand, with Maria’s Beach just to the north and Steps Beach to the south. Inside, there’s an open kitchen and living space that opens onto a front patio with sunset views, while outside guests share access to a pool, gazebo, grills, and an outdoor bar. It’s an easy spot for surfers or snorkelers who want the water only steps from the door.
Four guests, two bedroom
Price: $175 per night
Lighthouse-style home with ocean views in Amelia Island, Florida
North of Jacksonville, Amelia Island is a stretch of Atlantic coastline that stays mild through the winter, with daytime highs that make the beach a year-round draw. Fernandina Beach is the hub, with historic streets, casual seafood spots, and easy access to the sand. The quieter vibe sets it apart from Florida’s bigger resort towns, and in winter it feels especially calm.
This beachfront lighthouse is just steps from the ocean at Fernandina Beach. The New England-style home has three bedrooms, a wrap-around deck, and uninterrupted views of the Atlantic Ocean.
Six guests, three bedrooms Price: $533 per night
Luxury retreat with rooftop deck and sunset views in Orange County, California
See more photosTucked away between Huntington Beach and Seal Beach in a neighborhood dubbed “Sunset Beach,” this bohemian-feeling, peaceful seaside property was designed to give visitors a feeling of being transported to the tropical sands of Tulum. The stunning sunsets seen over the water will be breathtaking from each of the four levels to explore within this home that feels more like a resort.
Luxurious on-site at this property amenities include a Sonos sound system, a soaking bathtub, a bidet toilet system, a 3-car garage, and designer outdoor equipment, including beach bikes and bodyboards. Other amenities include a beachfront first-floor deck outfitted with a natural gas firepit and grill and enough lounge seating to fit everyone for an outdoor dining or stargazing session. There’s also a fully equipped kitchen with all the tools needed to create a tasty meal and three comfortable bedrooms — including a well-appointed primary suite.
Don’t miss the fourth-level rooftop deck, which is equipped with chaise lounges, a large sectional and 360-degree views—including the hills of San Pedro, the sparkling skyline of Downtown Long Beach, the Huntington Beach pier and Harbor, and, of course, the ocean.
Eight guests, three bedrooms
Price: $1,679 per night
Modern 3-bedroom villa with panoramic oceanfront patio in Rosarito, Mexico
See more photosThe crown jewel of this upscale, three-bedroom attached villa is likely the breathtaking ocean views from its enormous patio space overlooking the ocean. Listening to the sound of the waves below is the best way to relax within the recently remodeled, updated open-concept living spaces. Contemporary furnishings and amenities include high-speed internet access and a big flatscreen Smart TV in the living room. Cook in the modern kitchen, which features granite countertops, stainless steel appliances, and a water filter, in addition to a myriad of cooking tools and dinnerware.
The villa is a 5-10 minute walk from the festivities of downtown Rosarito, but peace and safety are paramount within the neighborhood due to a 24-hour security detail and gated community-only access. Other community-wide accessible amenities include a pool, sauna, spa and gym.
Six guests, three bedrooms
Price $185 per night
Newly renovated cottage with harbor views on Catalina Island, California
Take the Californian chilled lifestyle, add a dash of European island vibes, and you get one heck of a combo. That’s Catalina in a nutshell. It reminds me of the South of France or the Amalfi, and with quick one-and-a-half-hour transfers from three ports in South California, it’s a lot easier for West Coasters to get to than Europe. There are two towns on the island, Avalon and Two Harbors. Those wanting to stay in Avalon will need to book in advance, even in winter. As you might expect, Airbnbs and other holiday rentals are a hot commodity.
This newly renovated cottage is beautifully decorated, and when you’re not at the beach club, you can chill in the spacious private outdoor yard and take in the views of the harbor. There are three bedrooms and two bathrooms, and the location is spot on. It’s a one-minute walk to the grocery store and three minutes to the harbor and restaurants.
Six guests, three bedrooms
Price: $1,036 per night
87-foot water-tower-turned-home in Seal Beach, California
See more photosThis one-of-a-kind four-story, 87-foot Water Tower House is famed for its beautiful views and easy access to the local happenings of Seal Beach on the California coast. The structure itself dates back to 1892, initially serving as a source of water and power for Pacific Railway steam engines — but has since been converted into a home featuring three bedrooms, four baths, a family room, a dining area, and stunning views.
The elevator offers guests access to the first three levels. Up to the main level, admire the enormous windows with panoramic sights of the city and the scenery, and step out onto the wraparound deck, which has a jacuzzi. There’s a whimsical spiral staircase to reach the 4th and 5th Floors. The fully equipped kitchen has all the tools needed to make a yummy dinner, and the laundry facilities mean guests can extend their stay and keep fresh. The fifth floor features a well-appointed living room space with a bar, games, 360-degree views, and multiple Smart TVs for staying entertained any time of day or night.
Eight guests in four bedrooms
Price: $729 per night
Spacious 5-bedroom modern beachfront home with elevator in Oxnard, California
See more photosThis tasteful, upscale oceanfront home sits on Hollywood Beach in Oxnard, a historically favorite spot for celebrities to relax in their beach home. But this personally customized house itself is brand new. The property sits right on the sand — and was completed in December of 2018, featuring luxurious amenities like an elevator, four 70′ inch smart TVs, and a master bedroom perched up on the third floor showcasing unobstructed, panoramic views of the water below.
Seemingly, every room in the house boasts an impeccable view of the ocean. Watch the waves roll in from the large windows looking out onto the water in the living room space, relax in the luxurious soaking tub in the master bathroom (which also features sights of the ocean), or get cozy on the couch in front of one of the enormous televisions. There’s a large kitchen with an island to gather around and share a meal, and balconies on each level of the home to enjoy the fresh sea air and sunshine.
Fourteen guests, five bedrooms
Price: $786 per night
Elegant villa with ocean-view veranda and jetted tub in Laguna Beach, California
See more photosFeel like royalty in this large villa property boasting sweeping ocean views, an enormous patio, three bedrooms and two and one-half baths. Lounge out on the spacious, private, shaded veranda, which has a gas barbecue and chaise lounges. Rest in one of the comfortable and stylishly furnished bedrooms. Share a meal at the dining room table, surrounded by glass windows featuring sights of the blue sky and ocean below.
There’s a large skylight in the kitchen, letting in an abundance of natural light, and the stainless steel appliances and sleek countertops offer a great spot to make a home-cooked meal. Additional on-site amenities include a cozy gas fireplace, central air-conditioning, a large flat-screen TV, and a relaxing jetted tub in the master bath.
Eight guests, three bedrooms
Price: $1,069 per night
Minimalist home with balcony on The Strand in Manhattan Beach, California
See more photosThis clean, light-filled property is set on the iconic Strand in Manhattan Beach. Enjoy beautiful sea views and unparalleled beach access — just two elements that make this property feel exceptionally special. Gaze out the large windows onto the beach or step outside onto the balcony and breathe in the sea air.
Bright, modern design elements and a touch of vivid color in the furnishings add a bohemian flair to the otherwise minimalist decor. There’s a cozy living room with a large sectional, flatscreen TV, and a fireplace flanked by a wall of windows. The compact but functional kitchen has everything needed to make a home-cooked meal. It’s within walking distance of the sand and many shops and restaurants of downtown Manhattan Beach.
Five guests, two bedrooms
Price: $512 per night
