Water Mill, New York

A house in the

Hamptons

feels incomplete without a pool. This one is huge, with both steps and a ladder to get in and plenty of surrounding land for kids to play, plus a raised deck with lots of seating and loungers to recline on. The beach barn, with its exposed wood beams and high ceilings, is a great spot for a

family get-together

—there’s room for 10 guests across four bedrooms, including one with both a king and single bed inside.

Cabo San Lucas, Mexico

One look at this spacious

Cabo San Lucas

home—12 guests can sleep across six bedrooms—is enough to make us want to plan a

family reunion

. It almost doesn’t matter what’s inside: you’ll want to spend all your time in the backyard, dining al fresco, and taking dips in the pool, which overlooks Lands End. The inside more than measures up, though, with a U-shaped dining room with wrap-around windows, bedrooms that open up onto the patio, and a master bath as big as a studio apartment. And while the nightly cost is steep, a stay comes with resort-like perks including a $300 Cabo Expeditions credit and a free airport to villa transfer.

Stellenbosch, South Africa

After you’ve gotten your fill of

Cape Town

proper, head to

Stellenbosch

for excellent wine, top-tier restaurants, and a stay at this gorgeous, quirky property. The views are spectacular, and the lengthy lap pool is no doubt worth a dip, if only to take in the surrounding mountains from a cooler spot (the outdoor patio’s wood-burning fireplace is another amenity not to miss). You’ll want to spend the rest of your time exploring the home; it’s teeming with plants, shelves of books, and eclectic art.

New Smyrna Beach, Florida

Florida is hardly lacking pools, but this New Smyrna Beach rental (about an hour outside of

Orlando

) has one that measures a head above the rest: the sails keep it partially shaded, which you’ll no doubt appreciate on hot summer days. Surrounding the pool are lounge chairs, outdoor table seating, and a hammock, with an outdoor shower and soaking tub nearby. Inside, the modern home is all clean lines and white walls, with three bedrooms and two full bathrooms, meaning it can sleep up to six comfortably.

Tamarindo, Costa Rica

There’s a lot to love about this Costa Rican villa—

Traveler

editor Lale Arikoglu

has raved about

its views—which look out over Tamarindo Bay and the surrounding tropical forests—and outdoor hot tub. But the real treat, especially for a house 20 minutes from a rowdy beach, is the sprawling, secluded infinity pool, with its proximity to lounge areas (so you can chat with friends in and out of the pool) and wraparound ledges to sit and lean on.

Valladolid, Mexico

This Yucatan cottage screams

romantic couples weekend

, so whether you were doing

long distance

with your partner during quarantine or are ready for a vacation away from the kids, this colorful one-bedroom home could be the ideal spot. The dining and living area opens up to a private plunge pool; beyond that is open skies and greenery. The house itself is in the Yucatán jungle, 10 minutes away from the town of Valladolid, and is equipped with the basics: in the kitchen, you’ll find a full-sized fridge, a two-burner electric stove, a toaster, and a French press; there’s also Wi-Fi, air conditioning, and an open-ceiling shower.

Los Angeles

It’s hard to beat an infinity pool, especially one that looks out over

Los Angeles

. Combined with the hot tub, sun loungers, BBQ grill, and full-size bar, this backyard has everything you need for long, leisurely afternoons outdoors. The inside of this four-bedroom home is worthy of a stay itself, too, though with a massive kitchen and another bar; a big, airy living room; a spa-like soaking tub; and king beds in every room.

Tepoztlán, Mexico

This is the kind of home you go to get away, turn off your phone, and enjoy your surroundings—starting with this pool, where you’re welcomed by mountain views of Tepoztlán, a town about an hour and a half south of

Mexico City

known for its natural beauty (lakes, volcanoes, and waterfalls included). Past guests note using the patios to meditate, watch the sunset, and read. Inside, there are two queen beds in one large bedroom, making the space best for a couple or a small group of friends.

Palm Springs, California

In the desert heat

Palm Springs

is known for, a pool is a necessity, and this one is calling our name. Surrounded by resort-style lounge chairs, an outdoor daybed, and a covered patio, there’s plenty of room to grill, sit and read, and swim during lazy vacation afternoons. Inside, the home is bright and airy, with boho, desert-friendly touches like geometric wallpaper and woven wall hangings alongside mid-century modern furniture and all the amenities you could need, including a washer/dryer and dishwasher.

Austin

This modern farmhouse, which sleeps eight and has a backyard with space to match, is in an ideal

Austin

location, close to both

Barton Springs

and Zilker Park. But you could just as easily stay at home to enjoy the outdoors—there’s a sprawling pool and attached jacuzzi, with a large shelf alongside one end of the pool for keeping cool without full-on swimming (we’re already dreaming of laying out in that exact spot). Around the pool, you have everything you need to roast s’mores, cook dinner on the grill, or sit and stargaze; plus, the house is stocked with cornhole and board games.

Porto, Portugal

Any dreams you’ve had of owning a European country home can be (temporarily) met with a stay at this rustic, cozy home. The backyard is breathtaking, with an infinity pool jetting out over the

Douro River

and a multi-layered deck. Dining tables extend out from the living and indoor dining room, and the kitchen looks straight out of a movie set, with pots and pans hanging from the stone wall and all sorts of family heirlooms, from tea kettles to mismatched dishware and wicker baskets. With provisions like fruit, bread, cheese, and wine often left out for guests, it feels like a stay at your family’s (very beautifully located) cabin.

Monteroni D’arbia, Italy

If you’re dreaming of Italy, gather your family for a visit to Monteroni D’arbia. The house, one of our

favorites across Italy

, is split up into three apartments (so there may be other guests around), but this one is the largest, with two king beds and a pull-out couch in the living room. Outside, there’s an enormous swimming pool and plenty of space to spread out and relax while surrounded by sweeping views of the Tuscan countryside.

Waimea, Hawaii

When you’re not visiting the nearby Hapuna or Mauna Kea Beaches, take a dip in this gorgeous salt-water pool (or its attached jacuzzi). There are plenty of places to sit and relax both in the sun and covered by shade—the house is built around indoor-outdoor living, with sliding glass pocket doors that completely disappear from view. It has room for eight across three bedrooms, making it a great spot for families or groups heading to Hawaii.

Tulum, Mexico

Part of Holistika, a yoga and wellness center where you can book classes and massages, this Tulum home offers the best of both worlds when it comes to having private space with hotel-like amenities. There’s room for a whole crew—two of the three bedrooms have a king bed, and the third has two doubles; plus, there are three and a half bathrooms. We’d spend most of our time out back, though, laying in the hammock or cooling off in the pool.

Hudson, New York

For an Airbnb that feels more

like a trip to the spa

, consider this Hudson rental. It is secluded and spacious—perfect for city-dwellers looking to spread out—with a large lap pool and hot tub accessible from both of the bedrooms. (Even better, the pool can be heated, so visitors are able to enjoy it year round.) Inside, the modern home has two bedrooms, each with their own pristine glass shower.

Punta Arenas, Costa Rica

Another favorite

spa-like rental

, this Costa Rican retreat sits above the trees, with a view of the ocean. Of all the pools on this list, this one might be the most unique, with a sunken seating area smack dab in the middle. Enjoy hors d’oeuvres or an evening cocktail on the plush couch, or use it as a space to dry off after a dip in the pool. The home is great for multiple families; each of the four large bedrooms has a private bathroom, and the dining table fits up to 14.

Folly Beach, South Carolina

This massive Folly Beach home looks out onto the ocean, and sits just two blocks from the beach. Take in the sunset from the screened-in porch, or head downstairs to splash in the pool; there’s a grill down there, too, to get dinner going while kids play. Inside, there are five bedrooms, four and a half bathrooms, and a massive kitchen, shown above, plus a gas fireplace. To note, this is a two-story stilt home, so know it will require climbing many steps.

New Orleans

This dreamy guesthouse sits one block outside the French Quarter, close enough to walk to the busy neighborhood’s restaurants and bars as well as the nearby Frenchman Street, where you can find more local music. Despite the proximity, it serves as a quiet retreat, with a bedroom and bathroom upstairs, and a living room and full kitchen downstairs, plus lounge chairs out back. The host, who lives in the main home, has two friendly dogs that occasionally roam in and out of the courtyard—a plus in our book.

Topanga, California

One of our

favorite Airbnbs in California

, this Topanga mansion boasts incredible views and plenty of indoor and outdoor living space. Between the wood-paneled bedrooms, room-darkening shades, and floor-to-ceiling windows, it is the ultimate chill-out spot just outside L.A. in the Santa Monica Mountains. The main attraction, of course, is the huge infinity pool in the backyard, where you can splash around while looking at unobstructed mountain and ocean views. Not enough? There’s a hot tub and grill out back, too.

Graton, California

A solar-heated swimming pool, tiki bar, and infrared sauna await you at this eco-friendly California home, along with walking and biking paths just beyond the property. The home itself is outfitted with

hotel-like amenities

, from

Parachute

robes and multiple pillow options (hypoallergenic, feather, down, memory foam, etc.) to a clawfoot tub. It sleeps four, and is situated an hour and a half from

San Francisco

in Sonoma County, with multiple wineries nearby. To note, the home is currently only available for long-term rentals of 31 days or more.

St. Augustine, Florida

This St. Augustine tiny home has everything you need and then some: a fully-equipped kitchen, washing machine, comfortable king beds in both bedrooms, and, shown above, a petite pool with a tanning ledge on one side, leading into the deep end. Plus, a small dining table on the covered front patio for morning coffee or evening drinks. Past guests note the location is great for walking

into town

, too.

Holualoa, Hawaii

It seems almost sacrilegious to swim in a pool when some of the world’s

most beautiful beaches

are nearby, but that’s not stopping us from appreciating this resort-style Holualoa home. This infinity pool on the Big Island overlooks the ocean, and is set just outside the open-plan living room (with eight-foot pocket doors, so you don’t miss an inch of the view). The hardest part will be deciding where to post up: the poolside lounge chairs, the day bed, the hot tub, or the pool itself are all options. The two-bedroom, two-bathroom home sleeps four, and was built by the same people behind the

Four Seasons Resort Hualalai

with classic Hawaiian architecture in mind.