Vacation rentals with a pool in Delaware County

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

Experience a stress-free stay at this newly-updated condo in Afton! This 1-bedroom, 1-bath vacation rental features a fully equipped kitchen, modern furnishings, and resort-style amenities perfect for your whole group. Spend the day soaking up the sun by the pool, tee off at the on-site golf course, or take a short drive to the Grand Lake O’ the Cherokees for unbeatable scenic views! When the day is done, fire up the grill and enjoy a home-cooked meal on the private patio with the ones you love.

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, 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!

4.82 out of 5 average rating, 17 reviews

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.

Home in Kansas

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.

4.9 out of 5 average rating, 30 reviews

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.

Home in Grove

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!

Top guest favorite

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.

5 out of 5 average rating, 3 reviews

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.

Barn in Grove

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.

4.79 out of 5 average rating, 14 reviews

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

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.

4.84 out of 5 average rating, 49 reviews

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

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.

5 out of 5 average rating, 4 reviews

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.

Home in Jay

Eagles Nest 2, EN2

Take it easy at this unique and tr At Eagle Ranch Resorts, we embark on a singular mission to provide an unparalleled sanctuary of opulence and serenity, where luxury meets nature in harmonious equilibrium. We stand resolute in our commitment to deliver an extraordinary escape that transcends the ordinary, embodying the spirit of eagles soaring to new heights. anquil getaway.

4.9 out of 5 average rating, 30 reviews

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

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.

5 out of 5 average rating, 3 reviews

A spacious outdoor pool area features two inviting pools, one in a kidney shape and the other a circular design. Surrounding the pools are multiple brown wooden loungers arranged neatly on a light-colored deck, bordered by lush green trees and landscaped areas.

Apartment in Afton

Grand Lake Studio Condo at WorldMark by Wyndham

There is no cleaning fee and guests are not expected to clean anything upon departure! You can leave the condo as-is when checking out :) The resort requires a valid ID and credit/debit card for check in. There is a $250 refundable deposit required. Please provide the full name you would like to use for the reservation when booking.

Vacation rentals for every style

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Popular amenities for Delaware County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.54 out of 5 average rating, 37 reviews

Home in Grove

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!

4.82 out of 5 average rating, 11 reviews

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

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

MichaelRating, 5 stars6 months ago

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.

Home in Jay

Eagles Nest 3, Lodge EN3

Pretty nice place to stay.

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

SherylRating, 5 stars3 days ago

My family (5 adults and two children under age 3) had a WONDERFUL extended weekend at Robin’s place…wish it could have been longer! The view of the lake is stunning, and we kept saying, “it’s worth a million!” The pool, although not heated, wasn’t too cold, despite the rainy weekend; we all enjoyed it, especially our granddaughter. (Do be careful when walking on the tiled floors surrounding the covered patio—they get slippery when wet—we put towels down to help with that.) The beds were sooo comfortable…the best of any rental I’ve stayed at…AMAZING! There are TONS of towels (bath and beach), and a well-equipped kitchen. The home is in a gated, quiet community next to a golf course (very safe, luxurious surroundings). Robin was the ultimate host! She wants the best guest experience, and that’s apparent given her speedy communication. The home is new to the rental market, so there weren’t any reviews when I rented it, and I’m glad I didn’t let that stop me. See you again soon, Robin!!

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.

4.4 out of 5 average rating, 10 reviews

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.

Home in Grove

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.

MariRating, 5 stars11 months ago

Cozy cabin next to lake & pool

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.

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Condo rentals with a pool

A two-story building features a blend of natural stone and wood accents. Balconies are visible on both levels, each shaded by trees. A well-maintained lawn leads to the entry, complementing the serene outdoor environment.

Geir BørgeRating, 5 stars35 months ago

Grand Lake (Afton,OK) Luxury 2bedroom Resort Unit

Excellent place for our family stay with all needed facilities and walking distance from more activities right on the lake👍😀

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.

MichaelRating, 5 stars131 months ago

Grand Lake 2 br condo

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

Guest favorite

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 stars3 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.

Guest favorite

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!

Top guest favorite

An open living area features a TV mounted on the wall, surrounded by a modern furniture arrangement. A circular coffee table sits on a light rug, while accented walls of blue and white create a harmonious aesthetic. The kitchen area is visible in the background.