Holiday rentals with a pool in North America

Grace — Vintage Soul, Million-Dollar View + Horses

April 8th Update: This is a new listing! Next weeknight availability is: April 19th Next weekend availability is: April 18th Welcome to Grace, the Enchanted Bus — a handcrafted 1956 International Harvester school bus turned magical hilltop retreat. Nearly everything inside is wood or vintage metal. Grace has a second story with a bedroom and meditation loft (with a small mattress too). Perched on a hill with sweeping views of rolling countryside with horses that come right to the deck!

Guesthouse Las Palomas, Gila, New Mexico.

We are in Gila, NM! This is high desert, 83 ranch acres on Bear Creek, beside the Gila Wilderness, a private guesthouse w/private hot tub, amazing wildlife, beautiful views, dark night skies, reasonably fast Wifi (20+mbps), Internet TV, Tempurpedic Queen + Queen with Tempurpedic top, ORGANIC breakfast fixin's to start you off in a well appointed kitchen. Propane BBQ Grill. Dog friendly (only with all vaccinations and never left alone in house), eco-friendly. This is a vacation destination.

Sol y Luna Mountain Retreat Hacienda

Enjoy the lovely setting of this romantic spot in nature and discover the serenity in our cozy farmhouse. This private villa wraps you in a lovely and peaceful environment with majestic mountains all around. The house is fully equipped for your convenience. It is ideal for couples in need of a nice getaway or just reconnect with yourself and nature. It is on a gorgeous tropical private 3 acre estate with private pool. Located in Villalba, Puerto Rico, just 50 minutes from Ponce's Airport.

Heated Pool, Hot Tub, Playground & Outdoor Lounge!

Unwind in our cozy Hochatown cabin featuring a heated pool, hot tub, fire pit, and outdoor TV—perfect for lounging and nights under pines. Inside, you’ll find a fully equipped kitchen, fireplaces, and a family-friendly layout with king suites and bunk beds—ideal for group getaways. ⭐ “Highly recommend this Airbnb to anyone with kids!” - Roxy 🌄 HIGHLIGHTS ✓ Heated pool for year-round use ✓ Hot tub, fire pit, TV lounge & playground ✓ Family-friendly w/ king suites & bunks

The Aloha House - Hot Tub - Pool

The Aloha House is located just above the University and only 1.5 miles from downtown Ashland. Nestled up a hill in the forest, you'll be transported to your own little private resort-like getaway with stunning views, architectural design that brings the outdoors in, and ample space for dining and entertaining poolside. The property consists of two separate studios (both included) connected by a unique outdoor living space with a seasonal pool, spa, outdoor shower, bar & BBQ, and more!

Private Heated Pool, Hot Tub & Game Room Getaway

Cloud Level is a modern A-frame getaway made for relaxing and making memories, with a private heated pool, hot tub, and beautiful mountain views. Inside, you’ll love the bright open layout, cozy gathering spaces, and a game room with a pool table for nonstop fun. Outside, enjoy the fire pit, amphitheater-style lounge seating, and a covered patio with an outdoor kitchen and bar area—perfect for grilling, hanging out, and soaking in the scenery. Just minutes from Hot Springs favorites!

Wildlife Oasis Cabin

Almost Home Wildlife Oasis is a small ranch near the San Felipe Creek, located between Laughlin AFB and central Del Rio. This brand-new cabin has a spa-like feel for a relaxing getaway. The exterior includes a fire pit, grill, and a stock tank cowboy pool. With walking trails in which you'll see deer, rabbits, roadrunners, and some wonderful farm animals right outside the cabin, you'll fall in love with this unique Del Rio experience! (No outside animals allowed due to wildlife.)

Wildwood Ranch- Pool, Media Rm, Sport Ct on 160 ac

Get away from it all at Wildwood Ranch! The 3,600 square foot ranch house has recent updates with an open concept kitchen/dining/living, perfect for groups. The beautifully-decorated 4 bedrooms and 4.5 bathrooms will welcome you home after exploring the 160 acres of natural beauty! Take a dip in the sparkling pool, fish the ponds, hike miles of trails or relax by the campfire at night. Come enjoy some peace and quiet in the country- you may not want to leave!

Modern Design Close to the City, Far from Reality

Built in 1803 and transformed in the 1960s by renowned designer Ward Bennett, whose work lives in MoMA's collection, this classic stone barn is unlike anywhere you've ever stayed. Comfortable and stylish, we've designed this home to be the ultimate retreat; featuring a hidden pool, large greenhouse, Japanese garden, and plenty of spots to curl up with a good book. An inspiring and cozy escape for couples, creatives, and bookish types alike.

Tranquil river cabin with a 1950’s vibe

Watch evening sunsets, have cocktails on the dock or around the fire pit, enjoy boating the St Mary’s River, or bird-watching from the river room of this secluded space. Stargaze from the backyard (no light pollution here!). A boat ramp is nearby for boat launching. (Tie your boat up at our dock during your stay) 45 min. from Jacksonville Fl 45 min. from Fernandina Beach Fl 20 miles to Cumberland Island Ferry 25 miles to Okefenokee Swamp

CaveB Escape-2bd/2bth +HOT TUB +view+winery

Perched on a hill above the Columbia River with majestic views of the gorge and vineyards, sit a series of newly built luxury modern homes designed by Olson Kundig. One of a few homes with unobstructed views, Cave B Escape comfortably sleeps 6 adults and 4 toddlers. The perfect destination for couples, families, work retreats or concerts. Walk to the Gorge Amphitheater, winery, restaurant + spa. The list of extra amenities is endless!

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).