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Vacation rentals with a pool in Delaware County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Delaware County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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A private hot tub is situated on a wooden deck, surrounded by the warm tones of the log cabin. Large windows showcase views of the wooded surroundings, while outdoor seating can be seen nearby, inviting relaxation in nature.

5 out of 5 average rating, 7 reviews

Cabin 1 Morning Star

Your Romantic wooded cabin retreat near Grand Lake Oklahoma. At Pine Lodge Resort you will find yourself swept away into a peaceful retreat. This fantastic property offers a Studio style Log Cabin with a wood burning fire place, king or queen sized bed, sleeper sofa, TV, full bathroom, kitchenette, dinette table and chairs. Enjoy modern amenities like WiFi, Roku, AC, and heating. Outside on the deck you can enjoy the peaceful surroundings with your own Hot Tub, grill and outdoor table & chairs.

Top guest favorite

The garage features a putting green with artificial turf, golf clubs displayed on the walls, and a mural of a golf course. A comfortable seating area is included, along with a grill positioned nearby for outdoor cooking.

5 out of 5 average rating, 27 reviews

Golfers Paradise - TeeTime Hideaway

Take it easy at this unique and tranquil getaway. Less work and more golf is our motto here at Tee Time Hideaway. Nestled in the greens of Shangri La Golf located on Monkey Island you will enjoy this 1 bed, 1 bath condo uniquely decorated to be a Golfers Retreat in Shangri La Country Estates. Enjoy your central location just 1/4 mile from The Summit for your daily dose of iron. Furnished with a king size bed in the bedroom and a Queen size futon in the living room. Go long or go home!

An aerial view captures the modern retreat nestled among lush trees, with sunlight streaming through the canopy. The roof design is angular, and multiple vehicles are parked on a gravel area. The surrounding greenery enhances the natural setting.

5 out of 5 average rating, 15 reviews

Luxury House with Heated Pool/Pickleball/Lake View

You will love our spacious 6-bedroom, 5-bath retreat, complete with luxurious hot tub, heated pool and pickleball/basketball court. This contemporary home offers ample space for your group, ensuring comfort and privacy. Modern amenities, stylish decor, and a fully equipped kitchen make it the perfect home away from home. Enjoy the hot tub and the view of the lake. The game room boasts an 85" TV with PS5, Dart board and shuffle board. So much fun and relaxation to be had at the Fire Water Escape!

A cabin-style home with a red exterior is situated amidst a wooded area. The structure features multiple windows and a green porch. Stacked logs for firewood are arranged in front of the house, and the surrounding landscape is dotted with greenery.

4.87 out of 5 average rating, 23 reviews

The Hangout-Peaceful Ozark Hideaway

Your host has been on Naked and Afraid, so if you’re craving a rustic escape with comfort and character, this is it. Tucked away in the woods, this 3BR, 2BA cabin-style home sleeps 6+ & feels like staying at Grandma’s—simple, peaceful, & full of charm. Located in a quiet gated resort with trails, pools, golf, and river floats nearby. Close to Natural Falls, Fidler’s Bend, & Arrowhead Speedway. Perfect for families or couples wanting a slow-paced retreat. Not fancy—just cozy, clean, & welcoming.

An aerial view of the property shows a spacious home surrounded by greenery. A swimming pool is visible next to a patio area, and several cars are parked along a paved driveway. The layout demonstrates ample outdoor space for recreation.

Vacation home in Jay

4.82 out of 5 average rating, 28 reviews

Eagle Ranch Resorts - Lodge EN1

Relax with the whole family at this peaceful place to stay. From Mid-America outdoors events, large group retreats, family reunions, family vacations, and more. Our Family home is here for your get aways! With our fresh water spring on the property, pond to fish, 3 prime Oklahoma fishing lakes within 15 min boat loaded on water, Kayaking & tubing locally, or on the Illinois river, south 30 min you will find all the outdoors adventures you want! Please enjoy what we’ve made home!

A two-story residence features a blue exterior with white trim and a brick façade. A garage door is prominently displayed, while the front yard is landscaped with grass. A streetlamp stands nearby, providing lighting for the walkway. The surrounding homes add to the neighborhood aesthetic.

Monkey Island Getaway

Relax & unwind in this charming 2 bedroom, 2.5 bath condo located on Monkey Island. You will have easy access to Tera Miranda Marina boat dock minutes from the door & a community pool, fire pit & fenced basketball court. You will have access to the 2 car garage which is equipped with a Tesla charger & trailer parking for your boat. Whether you’re planning a weekend retreat or an extended stay this peaceful escape offers all the comforts of home with the added perks of lake life

A fenced community pool is set within a spacious grassy area, surrounded by tall trees. A poolside building with a covered patio offers shade and seating. The clear blue sky enhances the inviting atmosphere of the outdoor space.

5 out of 5 average rating, 23 reviews

#MonkeyIslandHideaway at Grand Lake, Oklahoma

Incredible 5 bedroom waterfront home, minutes from Shangri La resort (golf, spa, and restaurants) on Monkey Island. Well appointed and spacious, perfect for entertaining any group. Steps away from boat slip at community dock, community pool, and private hot tub on deck. 4 bedrooms and 3 bathrooms on the main floor, and an additional upstairs living area/bunk room with private bath. Plenty of seating for meals and additional space on the back deck overlooking the water.

A tiny home is featured, characterized by a charming exterior with horizontal wooden siding and multiple windows. A wrap-around deck is visible, bordered by a wooden railing. Steps lead to the entrance, offering access to the inviting outdoor space.

Tiny home in Afton

4.85 out of 5 average rating, 20 reviews

Monkey Island Hide Away

This is a great location to enjoy all the island has to offer. Convenient to restaurants, nightlife, Resort life, Golf , Lake life and much more all within minutes of this location. This wonderful tiny home is located on the island within Monkey Island RV Park. Included wiith your stay, you will have access to the parks playground, swimming pool, bath house and laundromat all located within the park. (pool opens May 1)

An outdoor swimming pool is surrounded by lounge chairs and features a gently curving shape. Adjacent to the pool, a building with a shaded area and landscaped trees enhances the setting. The area is enclosed by a fence, providing a sense of privacy.

Apartment in Afton

1BR Peaceful and Spacious Suite @ Grand Lake

This resort’s Midwestern hospitality makes every generation feel right at home. Covid-19 Enhanced cleaning protocols in place. • Guest checking in must be 21+ with valid ID. • Guest must have debit/credit card to put $150 refundable security deposit on hold at resort check-in. • Name on reservation must match photo ID at check-in. Please confirm your first and last name as shown on I.D when submitting a booking.

A clean swimming pool is surrounded by lounge chairs on a sunlit patio. A light-colored building with a trellis and greenery is visible in the background, accompanied by trees and a well-maintained lawn. Fencing encloses the area, providing a sense of privacy.

4.86 out of 5 average rating, 7 reviews

3 bedroom at Grand Lake

Situated on a peninsula in Grand Lake O' the Cherokees, an area known as Monkey Island in Northeast Oklahoma invites you to play on 60,000 acres of sparkling lakes and 1,300 miles of shoreline with every activity you can image in and out of the water. Grand Lake's friendly Midwestern hospitality makes every generation feel right at home, from newlyweds to tiny tots to doting grandparents.

A seasonal outdoor pool is surrounded by lounge chairs, set against a clear blue sky. A scenic view of a lake and lush greenery can be seen in the adjacent image. The interior features a cozy seating area with a television and dining table, illuminated by natural light.

Apartment in Afton

4.9 out of 5 average rating, 31 reviews

Grand Lake 2 Bed/2 Bath Condo Resort ~ Pool ~ Hot Tub

**Condo: spacious 2 bedroom/2 bath home (1,075 square feet) with a king bed in the master bedroom, two twin beds (request if you would like a Queen bed in the 2nd bedroom) in the guest room and one Murphy bed in the living room. Additional amenities include a full kitchen and dining area, fireplace, washer and dryer and balcony. Maximum occupancy is 6 people.

An inviting outdoor pool area features a large swimming pool and a separate hot tub, surrounded by multiple lounge chairs. The surrounding landscape includes greenery and a well-maintained building, creating a tranquil atmosphere for relaxation and leisure activities.

5 out of 5 average rating, 3 reviews

Scenic Lakeside Escape: 3BR at Wyndham Grand Lake

Experience the enchantment of Monkey Island in northeast Oklahoma, where 60,000 acres of shimmering lakes and 1,300 miles of pristine shoreline beckon you to indulge in thrilling water adventures. Immerse yourself in the unparalleled charm of Wyndham Grand Lake, offering a captivating King Bed Suite that promises an unforgettable retreat.

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Convenient locations with everyday essentials

Popular amenities for Delaware County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

4.47 out of 5 average rating, 45 reviews

Shared Hot Tub, Pool & Dock: Lakefront Grove House

A spacious dining area is highlighted by a large wooden table surrounded by chairs, with a modern design. Natural light filters through the windows, illuminating the open living space, which features a comfortable seating arrangement and a stone fireplace, providing a cozy atmosphere.

Home in Delaware County

4.83 out of 5 average rating, 12 reviews

Pool Access, Deck & Boat Slip: Monkey Island Oasis

An outdoor pool is highlighted against a backdrop of open fields and distant trees, framed by a textured patio surface. Two lounge chairs are positioned nearby, creating a relaxed setting for enjoying the sunny landscape.

Home in Gravette

4 out of 5 average rating, 5 reviews

Ranch life experience with private pool

An aerial view captures a serene pond surrounded by lush greenery and mature trees. A charming cabin can be seen in the distance, nestled among the natural landscape. The water reflects the vibrant colors of the foliage, creating a tranquil atmosphere.

4.67 out of 5 average rating, 3 reviews

Eagles Nest 3, Lodge EN3

Top guest favorite

5 out of 5 average rating, 6 reviews

Family-Friendly Home with Private Pool

A covered patio features a dining set with six chairs and a table, accompanied by a gas grill. Expansive views of the open landscape and distant lake are visible, creating a serene outdoor space for gatherings.

4.91 out of 5 average rating, 11 reviews

Near Shangri-La: Lake-View Monkey Island Home!

The living area features a neutral-toned sofa adorned with blue accent pillows, complemented by two blue chairs. Natural light filters through sheer white curtains over the windows, illuminating the space. Two lamps on side tables add to the serene ambiance.

Home in Delaware County

5 out of 5 average rating, 4 reviews

Cozy Monkey Island Townhome

A modern living area is highlighted by a bright color palette, featuring a plush yellow armchair and a cozy white sofa. Unique wall art adds character, while a sleek kitchen is visible with stylish bar stools and stainless steel appliances in the background.

Grand Lake Shangri La Country Estates Condo

Condo rentals with a pool

An outdoor hot tub is positioned adjacent to a swimming pool, surrounded by lounge chairs and shaded umbrellas. Palm trees provide greenery in the background, contributing to a relaxed atmosphere. The space is designed for leisure and enjoyment during warmer seasons.

Grand Lake 2 br condo

An outdoor pool is surrounded by lounge chairs, featuring a gently curving shape. The clear water reflects the blue sky, while a building with large windows stands in the background, alongside trees and landscaped areas.

5 out of 5 average rating, 8 reviews

Grand Lake, OK, 2 Bedroom T #1

The open living area features a comfortable sofa with decorative pillows, a round ottoman, and a large flat-screen TV. An adjacent kitchen showcases stainless steel appliances and a breakfast bar. Natural light fills the space through large windows, enhancing the modern decor.

4.86 out of 5 average rating, 22 reviews

Pool Access: Condo w/ Patio in Afton

Two outdoor pools are set against a clear blue sky, surrounded by a spacious patio. Numerous lounge chairs are arranged around the pools, providing ample seating for relaxation. The clubhouse is visible in the background, offering additional amenities.

4.8 out of 5 average rating, 5 reviews

Grand Lake, OK, 3 Bedroom #1

A two-story building is visible, featuring a combination of stone and wood exteriors. Lush green grass surrounds the structure, and several trees provide natural shade. Balconies are accessible from the upper floor, enhancing the inviting outdoor ambiance.

Club Wyndham Grand Lake, 2 bedroom Condo

Exterior of a two-story building featuring balconies adorned with black railings. Lush green lawns and trimmed bushes enhance the landscape, while vibrant pink flowers add a pop of color. A clear blue sky provides a bright backdrop for the setting.

Family Fun on Monkey Island in this resort 2BD con

A community swimming pool glistens under a clear blue sky. Surrounding the pool are multiple lounge chairs, and a shaded structure provides amenities. Lush greenery and tennis courts are visible in the background, creating a refreshing outdoor space.

4.91 out of 5 average rating, 58 reviews

Lofted Condo w/Golf Cart & Pool in Shangri La

An outdoor pool area features a large swimming pool and a smaller hot tub, surrounded by a spacious patio. Multiple lounge chairs are arranged along the poolside, with clear blue skies and green trees in the background, creating a relaxing atmosphere.

5 out of 5 average rating, 4 reviews

Scenic Lakeside Escape: 2BR at Wyndham Grand Lake

Other vacation rentals with a pool

An outdoor pool area features a spacious blue swimming pool, surrounded by a concrete deck lined with numerous lounge chairs. A separate hot tub is designed in an organic shape nearby, with trees visible in the background, adding a natural element to the setting.

Scenic Lakeside Escape: 2BR at Wyndham Grand Lake

A two-story resort building is nestled among trees, featuring a mix of stone and wood exterior. Balconies with railings are visible on several units, offering outdoor space. Lush green grass surrounds the building, providing a serene setting against the clear sky.

Scenic Lakeside Escape: 1BR at Wyndham Grand Lake

An inviting swimming pool area is surrounded by lounge chairs, offering a relaxing space for guests. A light-colored building is seen in the background, featuring large windows and a shaded patio space. Lush greenery and a tennis court are visible beyond the pool area.

2 bedroom grand lake fun

A sunset casts warm hues across the sky, blending oranges and yellows against a backdrop of dark clouds. Silhouetted trees and a barn structure are visible in the foreground, with open grassy fields extending towards the horizon.

Eagles Nest #5, EN5

A seasonal outdoor pool area showcases two pools, including a larger rectangular pool and a smaller, heart-shaped pool. Surrounding the pools are numerous lounge chairs arranged for relaxation, while a building with large windows and landscaped greenery is visible in the background.

Scenic Lakeside Escape Studio @ Grand Lake Resort

A spacious outdoor area features two swimming pools, one in a kidney shape and a rectangular design adjacent to it. Surrounding the pools are numerous lounge chairs positioned under clear blue skies and well-maintained landscaping adds greenery to the setting.

Scenic Lakeside Escape Studio @ Grand Lake Resort

A two-story building features a combination of stone and wood exterior, set against a green lawn. Balconies are visible on the upper level, providing outdoor space for guests. Lush trees border the property, contributing to a serene environment.

Scenic Lakeside Escape: 1BR at Wyndham Grand Lake

An outdoor pool area features two separate pools surrounded by a spacious deck. Chaise lounges are arranged neatly along the edge, providing ample seating. A building with large windows is visible in the background, and lush greenery borders the area.

Apartment in Afton

4.67 out of 5 average rating, 3 reviews

Grand Lake 2 Bdrm Condo Resort

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