Holiday rentals with a pool in North America

Cabin in the Country with Private Pool- Near Tulsa

Escape to your own cabin on a working 80 acre ranch in Haskell, Oklahoma. Enjoy a private pool with rock waterfall and slide, relax in the hot tub, and take in the quiet beauty of ranch life with horses nearby. Gather around the fire pit under the stars and enjoy peaceful country evenings. Pet friendly with approval. Perfect for a romantic getaway or peaceful retreat near Tulsa, with plenty of space to unwind, reconnect, and enjoy the slower pace of country living. Haskell Airport 12 min away!

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!

Hoss’s Tiny House

The tiny house is located behind a big garage with a large gravel parking lot. It is very secluded and quaint away from the main road. The parking area is behind at the back porch on the tiny house were you can sit and enjoy peace and quiet. We are 1 mi from South Holston Lake. 2 mi from Creeper Trail, 6 mi Main Street Abingdon, 8 mi downtown Bristol, 10 mi Bristol Speedway. We have farm animals in the fields beside the tiny house that are very friendly. All the farm animals enjoy visitors.

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.

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!

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.)

Casa Eden, Barra de Santiago. Motor boat included

Escape to Casa Edén, a beachfront and estuary retreat—perfect for sharing with family or friends. 🌊🌿 🏖️ Relax in the private pool with views of Barra de Santiago beach, or unwind on the deck overlooking the estuary, volcanoes, and mountains. 🚤 Craving adventure? Your stay includes access to a motorboat, kayak, paddle board, and even inflatable tubes for water fun. ✨ Here, every day becomes an unforgettable experience: relaxation, adventure, and memories that last forever.

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!

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).

Dew: Mirror Cabin w/ Private Pool + Hilltop View

Meet Dew—an Asian Zen mirror cabin tucked behind bamboo, with glass views over treetops and the river valley. Made for quiet mornings, warm baths and slow nights. Enjoy: ✔︎Panoramic windows + skylight stargazing ✔︎Private bamboo-fenced yard + expansive deck ✔︎Private pool + loungers ✔︎Luxury bedding + curated interiors ✔︎EV charger • BBQ • Fire pit ✔︎Special decoration available Breathe. Unplug. Come back to love