Vacation Rentals With Amazing Pools for Every Kind of Getaway

The Evolve Team
The Evolve Team
April 8, 2021

Vacation rentals with amazing pools offer an escape worthy of daydreams. In these places, you can cool off, bask in the sun, and spend golden hour al fresco, sipping a cocktail and enjoying the good times. 

We’ve rounded up our most-loved vacation rentals with amazing pools, sorted by the experience you’re seeking. Whether you’re booking a bachelorette party or family trip, we’ve got you covered on what to look for in a home. Pack your biggest shades, your favorite swimsuit, and a page-turner — then dive on in. 

Evolve Tip: Looking to explore all of our vacation homes with private pools? You’ll find them right here.

The Poolside Family Reunion Trip

No matter the size of your reunion, reconnecting with your out-of-state relatives at a private pool is a memorable way to escape. Lounge by the water together, show off the recipes you’ve each mastered since your last gathering, and spend evenings playing board games with a view. If you choose an especially scenic place (like one of our oceanfront vacation rentals with a private pool), you won’t even want to leave the house.

Evolve Tip: When you’re browsing family vacation rentals with private pools, look for inviting decor that will appeal to the whole group. Knowing that you each have your own routines and travel styles, we recommend finding a place with activities to do right out your door. We also recommend looking for escapes with multiple bedrooms and bathrooms so that everyone can stick to their own routine.

Take a Dip at This Oceanfront Vacation Rental with a Private Pool

Luxury vacation rental with private outdoor oceanfront pool

This glamorous Cozumel vacation home sleeps twelve, giving each of you some private space (with a total of four bedrooms and six bathrooms). The Caribbean Sea is the backdrop of your time here — and you can drink it in from the private oceanfront pool or the elegant patio, complete with hammocks. When night rolls around, fire up the gourmet grill that sits right on the sea and enjoy the quiet of having your own private pier. Those looking for fresh air can use the bicycles this owner provides. The home even features family-friendly touches like a fountain show in the pool and rafts for the kids.

The Curated and Cultured Poolside Trip

Shop for local treasures, wind your way through offbeat museums, and savor gourmet eats on a cultured escape with fellow design-lovers. Choose an interior that evokes your surroundings — including a tasteful pool that fits the aesthetic — and experience the destination you’ve chosen every moment of your stay.

Evolve Tip: If you’re looking to blend quiet, lazy afternoons by the pool with legendary eats and shopping, Palm Springs is a must-see destination. From retro-chic homes complete with pristine kidney pools overlooking the mountains to renowned bites (like any of The Infatuation’s ideas), it’s all here. To explore a little more, check out our Palm Springs page, filled with stunning homes and ideas of what to do while you’re in town.

Take a Dip at This Retro Vacation Rental With a Heated Pool in Palm Springs

Mid-century vacation rental with heated pool

Listen to Nancy Sinatra and nurse manhattans by the heated pool from a secluded, mid-century haunt in Palm Springs. You’ll know that you’ve arrived in an upscale desert hideaway as soon as you unpack and light the fire in the living room. Bright color splashes its way throughout the home, with furniture shapes that harken back to Palm Springs’s early days. When you’re ready to adventure out, tower over the area by tram, take a modern architecture tour, or shop your heart out.

The Winter Holiday Poolside Trip

Vacation rentals with amazing pools offer a luxurious chance to restore — and there’s no reason they should be limited to summer months. If you’re interested in traveling in winter or putting a unique spin on the holidays, an indoor pool lets you splash around in any season. For bonus points, search for amenities like a hot tub and fire pit that let you stay warm with a different view.

Evolve Tip: If you’re booking a family vacation rental with a private pool over the holidays, you might want some time to yourself to wrap presents or cozy up with a good book. Choosing a place that has a game room gives the kids a place to spread out that’s a bit more private where they can watch movies and play.

Take a Dip at This Family Vacation Rental With a Private Indoor Pool in Liberty Lake 

Family vacation rental with private indoor pool

Liberty Lake, WA, is an oasis for families. In less than an hour, you can drive to Mt. Spokane, where skiing, tubing, and winter play await. Hit the slopes together, then sip cocoa back at this stunning 5,000 square-foot vacation rental that sleeps ten people. Let the kids swim in this incredible indoor pool complete with toys, sit by the fire in the sophisticated farmhouse living room, or enjoy access to the lake just a block away. And yes, there’s even a game room with foosball.

The Special Occasion Poolside Trip

It’s just about time to catch up on the big occasions that last year made it challenging to celebrate — birthdays with your high school friends, the overdue bachelorette party, or an anniversary where you want to do something you’ll never forget. When you’re celebrating a special occasion by the pool, you’ll want a special home. Look for an immersive setting that will make for great photos, ideally with plenty of outdoor seating and places to spread out. This trip is less about going out and more about staying in and splashing around.

Evolve Tip: Make memories by cooking something new together, right outside. We recommend finding a vacation rental with an amazing pool that also has an outdoor grill set up. This way, you can grab local snacks and drinks before you arrive, then grill up burgers on the grill in between your afternoon and evening swim. 

Take a Dip at This Texas Vacation Rental With a Private Outdoor Swimming Pool on Pilot Point Ranch

Texas vacation rental with private outdoor pool

Every new room of this house is a photograph waiting to happen — from the outdoor/indoor seating gazebo with a grill overlooking the pool to the enormous couch by the fire in the living room. No matter what you’re toasting to here, it’s sure to feel festive as you admire eight acres of private ranchland.

The Pet-Friendly Poolside Trip

Embark on a tranquil, poolside getaway where everyone is included — even your pet. Let them nap in the sun while you swim, knowing that they’re able to relax too. Then, curl up together after dark for a night that feels just like being at home (without the mess or responsibility).

Evolve Tip: Many poolside escapes sit high on a hill (with landscaping that isn’t exactly pet-friendly). When you’re booking a pet-friendly vacation rental with a private pool, be sure to look for a place that has a grassy area where they can go outside or stretch their legs. Also, note the home’s specific pet-policy to find out if it matches your travel situation — the owner will often specify the number of pets allowed. You’ll also want to choose a place without the clutter that could become a problem for a pet guest. Luckily, all of Evolve’s homes are pristine and 100% ready for your arrival.

Take a Dip at This Pet-Friendly Vacation Rental With a Private Pool in Galveston, TX

Beachfront private pool at pet-friendly vacation rental

A serene tropical paradise awaits you at this palm-tree-laden Texas vacation rental with a private pool. Swims have a full resort feel here with an outdoor bar, palapa huts that invite you to retreat into the shade, and an outdoor hammock — and if you want to get out of the house, a long walk, you’re by the beach. This place welcomes up to two pets.

The Girls’ Poolside Trip

Arrive at a posh place in awe as you take in the gorgeous surroundings from enormous windows. Relive your favorite memories together and make new ones by the pool. Get a little silly by evening by having a dance party with a view — then enjoy a grown-up sleepover filled with popcorn, comedy classics, and some self-care. 

Evolve Tip: When you’re splitting your trip several ways, it gives you the freedom and flexibility to splurge on something glamorous. Opt for a breathtaking location and choose a house that will become a memory in itself. Think: beautiful scenery, impeccable interiors, and enough square footage that you can each have your own space.

Take a Dip at This Lakefront, Modern Vacation Home With a Private Outdoor Swimming Pool

Lakefront vacation rental with private outdoor swimming pool

Have that “wow moment” as soon as you walk into this unbelievable modern property with a sophisticated pool overlooking the mountains and Lake Chelan — which is home to its own wine valley, perfect for a midday tasting. From the top of the bluff, you can swim all day long, cook a family-style dinner in the beautifully appointed kitchen, and wind down in a bedroom that has a view.

Rest Easy by the Pool

Master your butterfly stroke without a care in the world. All of these vacation rentals with amazing pools are verified in person and backed by our Rest Easy Promise — meaning they’ll always be as pristine as you saw on our site. If your stay isn’t up to our standards, we’ll make it right.


Read Next: For more private getaways with unique scenery, check out this feature on our favorite tiny houses for rent. Or, find sun on an adventure to one of America’s best national parks.

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