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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

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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, 22 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!

A welcoming pool area is framed by shaded yellow umbrellas and lounge chairs. Two sparkling pools are visible, surrounded by spacious concrete patio. A stone building with signage is positioned nearby, complementing the serene, natural surroundings of trees and open fields.

4.82 out of 5 average rating, 17 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.

The living area features two comfortable sofas, a wooden coffee table, and a flat-screen TV mounted on the wall. Natural light enters through two windows, complemented by light-colored walls and a ceiling fan above. A patterned area rug enhances the space.

Townhouse in Afton

4.87 out of 5 average rating, 15 reviews

Walk to Lake: Family Gem w/ Pool Access in Afton

Discover where worries meet their end and the fun begins when you visit Afton! This 3-bed, 3-bath vacation rental in The Reserve community puts adventure on land and on water within your reach. Walk to Grand Lake O' the Cherokees for endless water recreation, visit Royal Horse Ranch across the road for horseback riding and wine tasting, or make a splash at the community pool. When you're not checking off the vacation to-dos, spend downtime in this townhome featuring all of the comforts of home!

A spacious outdoor area features a large infinity pool bordered by a stone deck. The home showcases an expansive facade with tall columns and large windows. Warm colors from the sunset reflect off the water, enhancing the serene atmosphere of the setting.

3.67 out of 5 average rating, 3 reviews

Luxury Resort Home - Stunning Clifftop Lake View

Luxury Clifftop Retreat at Grand Lake is spacious and perfect for the entire family. Perched high on a cliff, this stunning escape offers breathtaking views and frequent pelican sightings. 4 King BR | 4.5BA – Each with a private bath Infinity Pool – Feels like the Mediterranean Chef’s Kitchen – Perfect for entertaining 1 mile to popular dining, 2.5 miles to Cherokee Yacht Club Borders The Coves Golf Course F5-Rated Safe Room WiFi & High-End Amenities You won’t believe you’re in Oklahoma!

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

4.87 out of 5 average rating, 23 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 private outdoor pool is surrounded by a wooden deck with lounge chairs and tables under turquoise umbrellas. Lush greenery lines the edge of the pool area, and a bright yellow bucket adds a splash of color. Scenic views of the landscape are visible in the background.

4.9 out of 5 average rating, 31 reviews

Pool & Outdoor Kitchen: Grand Lake Getaway!

Enjoy life on the lake as it was meant to be when you stay at this Grove vacation rental! With over 2,000 square feet of outdoor space, this 3-bedroom, 2-bath home is like your own resort! Spend your days lounging by the private pool, fishing or canoeing at Honey Creek State Park, or simply enjoying the million-dollar shoreline views. With easy access to Elk River Marina, a cozy fire pit, and incredible fall foliage opportunities, you'll find plenty to entertain you during fall!

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, 19 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 spacious outdoor area features a large pool surrounded by lounge chairs and shaded seating options. Lush greenery and colorful shrubs enhance the landscape, while a well-maintained garden path leads to the patio area and house.

5 out of 5 average rating, 3 reviews

Rustic Red Barn No Cleaning Fee!

Luxury and rustic await you at Grand Lake. Nestled on the shores of a tranquil lake, the cozy Red Barn House exudes a magical charm that harmoniously blends rustic appeal with the serenity of waterfront living. The lake front is a mere 200 feet from the patio. The kitchen is a mix of delightful modern design and the living room boasts an open concept. Overall, the cozy Red Barn House is a charming and comfortable retreat that offers a unique living experience.

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

4.79 out of 5 average rating, 14 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)

A refreshing outdoor pool is framed by a spacious patio area, featuring numerous lounge chairs arranged neatly along the perimeter. A well-maintained building is situated in the background, complemented by trees and greenery that provide a serene setting.

5 out of 5 average rating, 4 reviews

Grand Lake Midwestern fun

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. Club Wyndham Grand Lake's friendly Midwestern hospitality makes every generation feel right at home, from newlyweds to tiny tots to doting grandparents.

A waterfront cabin is shown beside a calm lake, featuring a red exterior and light stone accents. A walkable path lines the water, with two chairs positioned on a concrete patio. Nearby, trees with slender branches provide shade, enhancing the serene lakeside setting.

Place to stay in Grove

4.84 out of 5 average rating, 49 reviews

Waterfront 1 Bedroom/Cabin I/Newly Remodeled

Groveport Resort consists of 10 waterfront cabins. The property has 500+ ft. of shoreline, two boat docks, a boat launch, firepits, and a waterfront bar & grill. All of this in a protected cove on beautiful Grand Lake O' the Cherokees. We're also located within the city limits of Grove, Oklahoma near dining, shopping and attractions. the sounds of nature when you stay in this unique place.

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, 30 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.

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Quaint homes, peaceful surroundings

Popular amenities for Delaware County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

4.53 out of 5 average rating, 38 reviews

Shared Hot Tub, Pool & Dock: Lakefront Grove House

JohnnaRating, 5 stars3 weeks ago

We had a fantastic stay! The host was incredibly welcoming and responsive, providing clear check-in instructions and helpful local recommendations. The space was exactly as described—clean, comfortable. Would absolutely stay here again and highly recommend this host to anyone visiting the area!

A spacious open-concept living area features comfortable seating arranged around a wooden coffee table. A stone fireplace and a mounted television serve as focal points. The kitchen is visible in the background, showcasing modern appliances and cabinetry.

Home in Delaware County

4.82 out of 5 average rating, 11 reviews

Pool Access, Deck & Boat Slip: Monkey Island Oasis

TristanRating, 5 stars2 months ago

We had a great stay, love spending time on the lake and be able to sleep comfortable

A modern kitchen offers white cabinetry and elegant light fixtures. Countertops made of marble extend across the kitchen, complemented by stainless steel appliances. Ample storage is provided with cabinets lining the walls, and a window allows natural light to illuminate the space.

Eagles Nest 3, Lodge EN3

MichaelRating, 5 stars6 months ago

Pretty nice place to stay.

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!

MiriamRating, 5 stars5 months ago

wonderful, peaceful, great place to stay .you will not be disappointed.

A spacious living area is depicted, featuring a large, comfortable sofa adorned with decorative pillows. A rich area rug covers the floor, while a sleek, brown armchair complements the space. Natural light enters through a window, highlighting the tasteful decor.

4.4 out of 5 average rating, 10 reviews

Dock & Pool Access: Lakefront Grove Home!

ChristinaRating, 5 stars21 months ago

Nice location. Deck isn’t as large as pictures make it look. Scorpion was in the kitchen. No linens for pull out couch. There was a scorpion behind the trash can. Came back one evening to find water on the floor in the kitchen. We only had 3 towels for 2 people for a wk.

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, 3 reviews

Cozy Monkey Island Townhome

MelissaRating, 5 stars12 months ago

My sister and I stayed here for a wedding. It was perfect! Very tastefully decorated. Cant think of a thing that it didn’t have.The beds were very comfy and the location was convenient to all the events. Britni was very accommodating. We would stay here again!

The exterior of the home features a charming stone façade, complemented by black shutters and decorative windows. A curved driveway leads to the entrance, flanked by well-maintained green grass and mature trees, creating a welcoming environment for guests.

Cozy cabin next to lake & pool

MariRating, 5 stars11 months ago

Stayed at this home over 4th of July weekend. Home was beautiful, roomy and beds were SO comfy. Big back porch and community pool steps away. It’s wonderful.

A spacious sleeping area features a large bed covered with a textured blanket. A piece of wall art depicting abstract landscape hues is displayed above the bed. Natural light filters through the nearby window, which is partially covered by blinds.

5 out of 5 average rating, 4 reviews

Eagles Nest 2, EN2

TaraRating, 5 stars3 weeks ago

shanes place is one of a kind beautiful serene area, friendly staff and proactive to our needs. took us on tours of the property my grandson is in love with the place. we had a very memorable weekend thank you Shane and your group for the memories made.

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

MichaelRating, 5 stars131 months ago

Magalie was great to work with. She was very responsive and helpful. Her listing/unit was as described.

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.

4.84 out of 5 average rating, 19 reviews

Pool Access: Condo w/ Patio in Afton

ReganRating, 5 stars11 months ago

Walking distance to the lake and golf course! Great place for two people.

A well-equipped kitchen is highlighted by stainless steel appliances and a spacious countertop, providing an open layout to the living area. A view of the community pool and tennis courts is visible through large windows, suggesting a bright and relaxed environment.

Monkey Island Bungalow ~ Pool ~ Golf~ Dogs welcome

LukeRating, 5 stars3 months ago

Great place to stay!

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, 56 reviews

Lofted Condo w/Golf Cart & Pool in Shangri La

Jane LouisaRating, 5 stars4 weeks ago

Had a great 6 day stay! Perfect stay for a couple & their fur baby.

A refreshing outdoor pool is surrounded by a concrete deck equipped with lounge chairs and tables. Lush greenery and trees are visible in the background, enhancing the serene setting. An umbrella provides shade next to the pool area, offering a relaxing space for guests.

5 out of 5 average rating, 6 reviews

On the Rocks Condo, The Best of Grand Lake

SethRating, 5 stars37 months ago

This place is adorable. It is perfectly located near all the Monkey Island and Shangri-la action. It is so nicely decorated and our guests said they slept well and enjoyed their stay.

The outdoor pool area features a spacious deck with several lounge chairs and umbrellas. A covered seating area includes a table and chairs, providing shade. The pool is visible in the background, surrounded by trees and well-maintained landscaping.

5 out of 5 average rating, 8 reviews

Shangri-La Condo Monkey Island

RaulRating, 5 stars20 months ago

Very relaxing and quiet, beautiful location We highly recommend staying at Dave's Place at country Estates on Monkey Island.

A community pool area features clear blue water with stairs leading into it. Surrounding the pool, lounge chairs are neatly arranged, and a shaded seating area is visible under an umbrella. A club house is seen in the background, framed by well-maintained greenery.

4.85 out of 5 average rating, 26 reviews

Monkey Island Retreat 59-1

Rachel and MontyRating, 5 stars10 months ago

John was a great host! Quiet location, spacious home, great proximity to the lake and restaurants!

The open living area features a cozy seating arrangement with light-colored furniture. A large island with bar seating is visible in the kitchen, accompanied by soft lighting from three pendant fixtures. Natural light floods the space through expansive windows, completing the inviting atmosphere.

4.65 out of 5 average rating, 17 reviews

*RETIREES*GOLFERS*. Classy condo with Cart!

RichardRating, 5 stars10 months ago

clean, simple, easy, close to Shangra- La, access to golf cart!!! Randy very easy to work with!

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