Vacation rentals with a pool in Hendry County

4.84 out of 5 average rating, 19 reviews

A cozy seating area features a blue sofa, two armchairs, and a circular pouf on a textured rug. A floor lamp illuminates the space, while a large mirror reflects the light. Natural elements are added with a potted plant in the corner.

Home in Moore Haven

Caloosa House

Unique River Retreat with modern amenities. dock usage, boat\trailer storage, pool and full laundry. Enjoy hunting, fishing & nature from this river front.Newly remodeled 2 bedroom, 1 bath house with large kitchen.Under 1 mile to boat ramp,15 minutes to Clewiston. Plenty of parking for multiple trucks and boats! horseshoe pit, cornhole setup and a canoe for four. charcoal barbecue grill and a beautiful pool with a deck. There is a dock on the river across the road where you can relax and fish.

A wooden deck features a set of stairs leading to a mobile home, surrounded by green grass. Colorful potted plants are placed at the base of the steps, and bright clouds are visible in a clear blue sky.

4.93 out of 5 average rating, 15 reviews

Mo's Lake O Retreat

Location! Location! Location! Sitting 2 miles (3-4 min drive) from the City of Clewiston in a nice rural setting. Over 1.5 acres to spread out and bring your Boats to do some World Class Fishing on our Beloved Lake Okeechobee. Plenty of room for parking Trucks and Boat Trailers. Bring the whole family to enjoy our property and make sure to use the Swimming Pool! This home is very roomy with a huge kitchen and living area. We hope you love it here and enjoy your stay in America's Sweetest Town!

4.88 out of 5 average rating, 130 reviews

A well-maintained entrance is framed by a landscaped area featuring a pink flowering tree and small shrubs. The pathway, made of pavers, leads to an archway, while a garage door is visible to the right, complementing the modern architectural style.

Guesthouse in Ave Maria

Cozy, private two-room suite

A cozy, modern space in a family-friendly town. This two-room apartment with private entrance is in walking distance of the University, restaurants, shops and a Publix grocery store. Equipped with kitchenette. Smart tv in living area. A queen-sized bed with a full bathroom and a walk-in closet. Twin air mattress and Pack ‘n play available. Amenities in town include a waterpark with waterslides and swimming lanes, playgrounds, walking and bike trails, tennis and pickleball courts.

4.73 out of 5 average rating, 22 reviews

A swimming pool is set against a backdrop of lush greenery, surrounded by a tiled patio with geometric patterns of grass. A shaded area is provided by a large umbrella, while a rustic structure can be seen in the distance, with hammocks hanging nearby.

Farm stay in Clewiston

Luna’s Ranch - Clewiston

Get away from it all when you stay in Luna’s Ranch. This ranch offers families and friends a serene environment that can be jam packed with outdoor activities! This home sits on a 25 acre plot of land which includes 2 lakes, a barn, and farm animals/dogs. During the day go out mudding (ATVs not provided, but allowed) and explore the beauty nature has to offer, and at night sit out by the fire pit and stargaze. Don’t miss out on your opportunity to experience real country living!

5 out of 5 average rating, 62 reviews

A green sign displaying 'Paradise Ranch' is supported by a stake in front of a palm tree. The palm tree's long, fan-like fronds are visible, surrounded by a grassy area that extends into the natural landscape.

Farm stay in Clewiston

Paradise Ranch

Welcome to Paradise Ranch, your ultimate getaway from the city life! Imagine unwinding beneath a breathtaking starry sky by the fire pit, surrounded by nature's tranquility. Our RV is nestled on five acres of private land, offering you the perfect setting to immerse yourself in Florida’s great outdoors. Plus, we’re conveniently located just 30 minutes from Lake Okeechobee. Traveling with a trailer or a boat? No worries—there's ample parking space available for your convenience.

5 out of 5 average rating, 54 reviews

A close-up of a horse's face is featured, with large ears perked up and a prominent nose in the center. The textured ground and wooden fence are visible, creating a rustic setting that captures the essence of the surrounding farm environment.

Home in LaBelle

The Salty Cracker

The Salty Cracker has what LaBelle encompasses; tranquil cottage on a 14 acre hobby horse farm 2 miles from downtown. Surrounded by hundreds of undeveloped acres with century old oak trees, hog, deer, turkey. Park ur boat/trailer,RV under covered pole barn with electric/water hookups. Ice machine, bicycles, Pickleball court, swamp buggy tours/pontoon boat rentals available. Same price nightly whether there is 1 guest or 4! Hot tub/mini pool brand new and ready for you to relax.

A pool area is visible, featuring a clear blue swimming pool surrounded by palm trees. Several lounge chairs are positioned nearby on a sunlit patio, offering a relaxed atmosphere. The building's exterior can be seen in the background, completing the scene.

4.99 out of 5 average rating, 83 reviews

Lake Okeechobee Condo! #131

Ground flood, corner condo on the Big Lake Okeechobee. High speed wifi. Short walk to the Tiki Bar Restaurant. Modern decorations, basic amenities, comfortable home-like atmosphere. USB charging ports in bedrooms. Remote controlled ceiling fan. Remote controlled dimmable lights in living room. Nest smoke alarm/carbon monoxide detector. Keurig K Cup single cup coffee brewer. Molekule air purifiers for allergies and clean, fresh air thoughtful the home.

4.94 out of 5 average rating, 113 reviews

A spacious backyard features a pool surrounded by lush greenery. Two umbrellas provide shade over patio seating, while deck chairs are positioned nearby. A grill is visible adjacent to the pool area, offering an inviting space for outdoor gatherings.

Home in LaBelle

Ft.Myers- Labelle- Okeechobee Pool Vacation Home

This is a newly renovated, beautiful vacation home for the whole family, or you and your friends. It is a 2/2 that sleeps up to 6 comfortably. The centerpiece is a three seasons room that opens on all sides, adding an extra spacious feeling to the whole place. Also included is a newly installed, state-of-the-art Pool which is perfect for a getaway in the Florida weather! (***Pool heater available from November to March upon request at additional electric fee***)

5 out of 5 average rating, 11 reviews

A spacious outdoor seating area is framed by a wooden pergola with hanging plants. Several blue chairs surround a central fire pit, set on a paved patio. The area is surrounded by greenery, providing a tranquil space for relaxation and gathering.

Ranch in Clewiston

Rancho Rosa: Your perfect getaway

Our ranch is the place where nature and relaxation come together for an unforgettable experience. come and enjoy a soothing weekend at our ranch,surrounded by beautiful scenery and outdoor activities.This home is the ideal place with 2.5 acres of land for total enjoyment whether it's with family,friends, and pets.With a wide variety to make your vacation the perfect place. With ample space to park Rv,boats,vans,motorcycles etc

An aerial view showcases the layout of the condo complex, highlighting the heated pool and tennis court surrounded by green spaces. Nearby, the Roland Martin Marina and Tiki Bar are visible, with the scenic surroundings and open spaces providing a sense of the area's community and outdoor activities.

5 out of 5 average rating, 26 reviews

*LakeView * Fresh & New* Bass N Sun* Pool*King Bed

Take a break Discover the charm of this delightful 2-bedroom, 2-bath condo located at the renowned Roland Martin Marina. Immerse yourself in the ultimate bass fishing paradise or embark on an adventure along the Okeechobee Trail. Unwind at the Tiki Bar and take a dip in the heated pool. or tennis court This condo offers a cozy and comfortable living experience in a prime location.

4.95 out of 5 average rating, 22 reviews

A sleek kitchen features modern cabinetry and stainless steel appliances, including a large refrigerator and oven. A central island with seating for three is highlighted, complemented by overhead pendant lighting. Natural light filters through the space, enhancing the openness and inviting feel.

Apartment in Ave Maria

Lux Boutique Golf Course condo

Brand new 2/2 condo, with 1 king and 1 queen beds. this beautiful place has an amazing golf, lake, and sunset views. You can play all day long at the 18-hole golf course. Pickle-ball, biking, and walking trails are available. Tennis courts, 2 pools, restaurant, Gym, and many more amenities soon to be finished. Guarded and gated community. 1 Designated covered parking spot.

4.87 out of 5 average rating, 211 reviews

A circular swimming pool is surrounded by wooden decking and palm trees, offering a serene view of the open landscape. A ladder provides access to the water, and a built-in seating area is visible in the center of the pool.

Cabin in Clewiston

LOG CABIN at The Florida Ridge

Welcome to The Florida Ridge! Get the charming log cabin experience, with all the modern amenities. Connect with nature when you wake up to a beautiful Florida sunrise over 100 acres of privately-owned, open landscape. From hiking to swimming to roasting marshmallows by the fire, there is something for everyone at this South Florida home away from home.

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Popular amenities for Hendry County rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

A cozy living area is presented with a black sofa bed, accent pillows featuring the word 'home', and a decorative wall hanging. A large window allows natural light to brighten the space, complemented by a small side table with a lamp and a potted plant.

4.87 out of 5 average rating, 15 reviews

Fenelo Ranch

RandalRating, 5 stars2 months ago

Really nice place to stay at. Very clean.

An aerial view captures the lush green golf course, with winding fairways surrounded by tranquil water bodies. The landscape features manicured grass, framed by a smooth path for walking or biking along the edge, showcasing a serene outdoor setting.

Home in Ave Maria

Beautiful, Golf, Pool, New Condo

PaulRating, 5 stars2 months ago

This is a nice, clean condo with some resort amenities in a community that provides golf opportunities if that's what you like. The development's resort amenities are still in the growth stage as of this writing (April 2025), meaning that the restaurant has shorter hours and a smaller menu than may be desired, and the off-development dining options in Ave Maria are somewhat limited. Its a long-ish drive back and forth to Naples to find larger commercial centers.

An outdoor deck features a private pool surrounded by lounge chairs and a table set for dining. Covered by a wooden pergola, the space includes bench swings and views of the lush landscape under a clear blue sky.

Home in Moore Haven

4.8 out of 5 average rating, 10 reviews

Moore Haven Getaway w/ Deck & Private Pool

WillRating, 5 stars12 months ago

Everything was better than we expected! We booked this house at the last minute because the community pool at our home was closed for repairs and we had 3 grandchildren visiting!. Our principal requirement was A POOL- but we got so much more! The home was easy to find, the communication with the host made entry quick and easy and the place was spotless and larger than we anticipated. The kids spent hours in the pool, we cooked and ate without hunting for the right utensils - we had everything we needed. This was the absolute perfect place! Great home, great amenities and a great host.

4.75 out of 5 average rating, 4 reviews

A modern dining area features a large rectangular table surrounded by softly upholstered chairs. Abstract art pieces adorn the walls, while natural light filters through striped window coverings, creating an inviting space. Access to the outdoor area is available through sliding glass doors.

Home in Naples

Luxury Gated Estate w/ Pool, Wine Bar & Fire Pit

JenniRating, 5 stars8 months ago

Alvaro and Helen's home is wonderful! It is so understated in the listing description and the pictures. From the moment you step through the courtyard doors you know you're in for something special, truly a LUX home. The home is appointed with high quality EVERYTHING. From decor to coffee machines. You really feel like you are staying at a top five start retreat. The house has little touches and comforts that you don't get at a five star hotel which make it even better. There are items for children, for adults and even pets. It was hard to believe this home was pet friendly, it was one of the very cleanest Airbnb's I have ever stayed in. The host's are absolutely amazing as well. Extremely responsive, kind and generous. They have taken the time to make your stay enjoyable and comfortable. If you book this home, you will not be disappointed!!! Thank you for a fantastic stay!

5 out of 5 average rating, 6 reviews

The cozy living area features a sectional couch adorned with decorative pillows. A coffee table with a decorative centerpiece sits in the center, complemented by a classic writing desk and wooden shelves filled with books and media. Light filters in through the two windows, enhancing the warm ambiance.

Home in Moore Haven

Tropical Heart House

LaurieRating, 5 stars3 months ago

we loved Thomas's place on the canal! The place was private and had everything you could possibly need. we absolutely loved it. The neighborhood was friendly and it was a beautiful spot on the canal.

A single-story yellow home is framed by large oak trees. The well-maintained lawn features green grass and flower beds. A driveway leads to the garage, while a storage shed is visible in the background against the open space.

Home in LaBelle

4.71 out of 5 average rating, 17 reviews

Quiet and Relaxing

SharonRating, 5 stars4 months ago

Bed was very comfy. Rendal's place had all the necessities we needed plus some we didn't use even a travel mug to bring coffee with me in the morning. When we had a question Rendal answered us right away. Great TV in the living room and bedroom.

A modern single-story house is depicted at dusk, with warm light glowing from the windows. A wooden fence marks the perimeter of the property, set against a backdrop of trees and a colorful twilight sky.

4.87 out of 5 average rating, 47 reviews

Rancho Los Pinos Pool/Tiki/Private parking

GilRating, 5 stars2 weeks ago

great space amazing back yard

An expansive wooden deck surrounds a round pool, providing ample space for relaxation. A green landscape with trees and open fields is visible in the background. The deck features a smooth wooden surface, and the pool is equipped with a staircase for easy access.

SuzanneRating, 5 stars1 month ago

Cozy home for Vacations

Very comfortable so clean and beautiful pool great place to go and relax like 1 hr from the Everglades to go fishing fish hard and then come home to a home away from home..locked gate so everything is secured ...give this place 10 stars...

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Condo rentals with a pool

The kitchen features white cabinetry and a dark granite countertop. Stainless steel appliances, including a refrigerator and stove, are visible. A dual sink is positioned in front of the bar table, with assorted kitchen utensils and a coffee maker on display.

5 out of 5 average rating, 13 reviews

Bass & Sun Condominium Lake View !!! 2/2 Bedroom

YauheniRating, 5 stars12 months ago

next time we would like to stay here, very satisfied, very good host

A spacious living area is presented with a dining table featuring wooden chairs and a neutral tablecloth. Large windows allow natural light to fill the room, complemented by potted plants. A cozy seating arrangement invites relaxation, with decorative pieces enhancing the aesthetic.

Condo in Ave Maria

4.73 out of 5 average rating, 49 reviews

5080 Annunciation Circle, # 1206 Ave Maria- 3BR/2B

TeresaRating, 5 stars2 months ago

Our family loved staying at Mary’s condo. It was located right downtown on the circle. Perfect location to take my kids downstairs for some ice cream and shopping. It was clean, quiet, lots of parking, friendly and responsive host, and had everything we needed. We cannot wait to visit again!

A serene lake scene is depicted with a lone figure standing on a small boat, silhouetted against a vibrant sunset. The sun casts warm orange and yellow hues across the sky, reflecting on the calm water surface, surrounded by faint outlines of grass along the shore.

5 out of 5 average rating, 9 reviews

Fishing Paradise! 2/2 Bed Condo

AndrewRating, 5 stars1 month ago

Myself and a few friends came to this spot to do some fishing for the week. Very clean with an appropriate amount of dishes to be used throughout the week. There were 2 dishwasher soap tabs available. Even had a small amount of laundry detergent on hand. That was very helpful, even though I pack enough clothes on trips to last me the entire time it was nice to be able to wash them there instead of having to transport them home dirty. Will definitely stay again!

An open living area is showcased with a glass-top dining table surrounded by four light-colored chairs. A cozy lounge space features a sofa and wall-mounted clock. Large sliding doors offer access to a deck, with light flowing in through sheer window treatments.

Condo in Ave Maria

4.88 out of 5 average rating, 81 reviews

5080 Annunciation Circle, # 1205 Ave Maria- 2BR/2B

DonaldRating, 5 stars1 month ago

Thus was a very welcoming home. The only downside of the stay was no ceiling fan in master bedroom.

A two-level condo building is displayed under a partly cloudy sky. Green palm trees are seen in front of the structure, and a black vehicle is parked in the designated lot. The building features a metal roof and a welcoming exterior.

4.91 out of 5 average rating, 32 reviews

Lake Okeechobee Condo! #133

MistyRating, 5 stars1 month ago

Jason was quick to answer our questions and helpful with check in. His home is beautiful and the location is perfect. We rent this unit every year and if available we plan on coming back again next year. Highly recommended. He is an amazing host.

A modern living area showcases a sectional couch positioned facing a flat-screen TV mounted on the wall. A round glass coffee table is centered in front of the couch, while sliding doors lead to a balcony with outdoor seating.

LukeRating, 5 stars10 months ago

Bass & Sun Modern & Pool View !

Nice clean place, easy access and walking distance to a restaurant. A/C felt amazing! Fully stocked with everything you need as far as dishes, towels, and extra bedding!