Vacation rentals with a pool in The Villages

4.95 out of 5 average rating, 122 reviews

Home in The Villages

2/2 custom pool home with 4 person gas golf cart

TracyRating, 5 stars5 months ago

Great place. Very comfortable. Loved the pool and driving golf cart was fun. We had everything we needed for a great stay. This is not a complaint at all more of a helpful hint but one of the town squares was too far to take golf cart and you will need a car.

5 out of 5 average rating, 15 reviews

Home in Inverness

Vacation home with astonishing view of golf course

BiancaRating, 5 stars9 months ago

What an Amazing trip supported by a phenomenal host, Chris. Chris is attentive to every detail. I have booked again for November and looking to do so again for next summer. Thank you Chris for making all of our experiences, memorable s ones.

4.98 out of 5 average rating, 380 reviews

Guesthouse in Leesburg

Silver Lake Guest Pool House

KellyRating, 5 stars2 weeks ago

You guys have to hear this about our host. This is a bit of a conundrum because if I tell you this there won’t be a spot for us to come back. Being our first booking and stay at a airbnb it was wonderful spot and Tommy was a great host. The property itself was very well kept. The pool house was spacious and spotless. The kitchen was well equipped as I like to cook. The internet service was available with easy to follow instructions. We had the pool to ourselves and every morning Tommy would be out making sure any leaves were swept away. Tommy was always free to talk and always had time to answer and questions about where to ride the bike that day. We would highly recommend this place and will always remember the new friend we made!

5 out of 5 average rating, 75 reviews

Home in The Villages

Calming Pool Oasis in Fenney, The Villiages FL

JeanneRating, 5 stars1 month ago

This house in The Villages served as the perfect home base for our "mature" girls' trip. It had all the essentials we needed for our three-night stay and was located in a great area, just a short distance from Brownwood Square and close to a bike path. Situated on a quiet street (then again, most streets in The Villages are peaceful), we were able to relax without any disturbances. The home was outstanding. We did encounter some miscommunication with the owner/property manager regarding access to the amenities, and unfortunately, we weren't able to enjoy the full privileges that The Villages are famous for. However, the lanai and pool were lovely additions which enhanced our stay. The patio area provided a great spot for relaxed conversations. I highly recommend renting a golf cart before your stay to avoid the hassle of calling around town to find one, after arrival. We really appreciated the option of a short term rental, often hard to find in the Villages.

4.87 out of 5 average rating, 142 reviews

Home in Apopka

Country Pool home on 2 acres-30 minutes to Disney

LoganRating, 5 stars4 days ago

This Airbnb was the perfect spot for my family, Not only was Natalie incredibly accommodating but we were amazed at her instant communication. Every single thing you need for your vacation she already has waiting for you there. Don’t miss out on this place. 10/10 recommend

4.92 out of 5 average rating, 257 reviews

Guesthouse in Orlando

Modern Guest Studio (Private) Pool / Spa available

BrandiRating, 5 stars1 week ago

Had a great stay, communication was great. We had a small hiccup with the hot tub and problem was solved very quickly. The only thing I would complain about and not really complaining is there were cloths and a used towel hanging on the back of the bathroom door. No biggie and honest mistake by cleaners other then that the stay was amazing and felt like home away from home. Will stay again for sure

5 out of 5 average rating, 23 reviews

Villa in The Villages

The Coconut Courtyard-Private saltwater Pool-clean

RobertRating, 5 stars2 months ago

This is a very comfortable property. Good location to several town centers and the neighborhood recreation center. The owners were very responsive, always within minutes of my inquiry. A very nice outside area and a heated pool that was used every day. I would be happy to stay there again.

4.93 out of 5 average rating, 27 reviews

Home in The Villages

Private Pool, Lake View, & Golf Cart! 2 King Beds

MarlaRating, 5 stars2 weeks ago

Awesome home, clean, well decorated, fully stocked with .ended supplies in bathroom and kitchen. I want to thank Steve personally for responded to our needed reservation changes. He responded quickly to my request, and made it happen to meet our needs. I was certainly pleased with a credit for changing to less days at property. We will definitely look for Steve as a host in the future, including this same property next year, if available. Definitely would want to work with Steve again! Thank you, Steve!!

4.92 out of 5 average rating, 75 reviews

Home in Wildwood

New, private pool getaway in The Villages, FL

Jeffrey AlanRating, 5 stars1 month ago

We really enjoyed staying at Karens. The home was impeccable. The kitchen was well-stocked. The house feels spacious and is well-lit with lots of comfortable seating. We really enjoyed the pool and lanai area. The house is within walking distance to the Sawgrass square that has restaurants and stores (including grocery store). There is also live music at the square every night that ends at 9pm. We rented golf carts to tour the different communities. It was a lot of fun. We would highly recommend this rental and hope to come back soon.

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Popular amenities for The Villages rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.81 out of 5 average rating, 26 reviews

Home in Ocala

Family home in quiet neighborhood

StephanieRating, 5 stars6 months ago

We had a wonderful stay as we were visiting during a horse show at WEC. The fully fenced large yard was perfect for our dogs to play & exercise in. The enclosed pool area was very nice! We were able to comfortably spread out in this nicely laid out house with plenty of privacy. My only complaints would be bathrooms lack good water pressure and the beds were hard and would recommend getting either toppers or new mattresses for better comfort.

4.93 out of 5 average rating, 15 reviews

Home in Ocala

Pool House 1 Mile From World Equestrian Center

ChristopherRating, 5 stars4 months ago

Great location, great home! Very comfortable, would stay here again!

4.86 out of 5 average rating, 29 reviews

Home in Floral City

Private Resort Pool

JoeyRating, 5 stars1 month ago

Kelly was an awesome host—highly responsive and made everything super easy. The house itself is straight out of a magazine—beautifully designed and spotless. The location is perfect, especially if you're playing at Cabot Citrus. After a long day on the course, coming back to unwind by the picture-perfect backyard and pool was exactly what we needed. Would absolutely stay here again!

4.88 out of 5 average rating, 64 reviews

Home in Spring Hill

Heated Pool Luxury 4BR/2BA Home Close to Beaches

jenniRating, 5 stars2 months ago

Bang for buck is what you get with this stay. it was everything I hoped it would be and then some. Everything was nice and clean and easy to find and Zelijko was very responsive and helpful every stepmother the way. I would gladly recommend this stay and if ever in the area again would happily seek to stay here again.

4.97 out of 5 average rating, 66 reviews

Home in Orlando

The Perfect Home - Heated Pool - Next to Universal

EricRating, 5 stars2 weeks ago

Jesus was an awesome host! Always responsive and gave easy to follow instructions. We did a bunch of fun activities in Orlando but the best part was this beautiful home! Very well decorated, cozy, and the fully enclosed backyard and pool gave the ultimate privacy! I recommend this home over any Orlando resort! We will definitely book again!

4.87 out of 5 average rating, 143 reviews

Home in Clermont

Our Poolhome by the Mouse house with Game Room.

DonovanRating, 5 stars4 months ago

Our family loved the home. Carmen is a wonderful proactive host. Sincerely, thank you for being a vital part of our Disney vacation.

4.89 out of 5 average rating, 146 reviews

Home in Spring Hill

Florida Gulf Coast. Sunshine and warm breezes!

DonaldRating, 5 stars1 month ago

Paul is a very accommodating host. We had no issues and Paul periodically checked in with us to make sure everything was OK. The house was exactly as described. The pool was wonderful!!! This was our second stay at this property. We enjoyed it even more this time. Would stay again . Thanks Paul

5 out of 5 average rating, 16 reviews

Home in Wildwood

The Villages pool property with a 4-person cart!

BarbaraRating, 5 stars1 week ago

Our family enjoyed this home very much. The house was roomy with a modern kitchen and the little outdoor kitchen area was very nice. The pool was a great size and having it heated helped a lot in April weather. The location is a little farther out but we enjoyed the area very much. It was just a short five minute golf cart ride to the Sawgrass Grove area. Dave was very helpful and easy to work with. I highly recommend this home.

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Condo rentals with a pool

4.92 out of 5 average rating, 105 reviews

Remodeled 2BD/2BA Condo mins from Universal Studio

JtRating, 5 stars1 week ago

An awesome stay for a week! we recommend this place for anyone wanting to be in a great location near everything on International Drive. Host Maxine is great and helped when we needed it. Thanks Maxine! We will be back.

4.81 out of 5 average rating, 435 reviews

Amaranta/Studio beautiful balcony LAKE VIEW 🫶❤️

TamrinRating, 5 stars3 weeks ago

An amazing place to stay & so close to downtown Orlando

4.91 out of 5 average rating, 215 reviews

Deluxe Studio:Lakeview, parking, pool

ZavianRating, 5 stars2 weeks ago

Patrick and Sara have a clean, well maintained space, as well as a thorough and thoughtful approach to hosting. Our stay was nothing short of phenomenal, would certainly recommend it here.

4.81 out of 5 average rating, 381 reviews

Condo in Orlando

ORLANDO SUITE@ UNIVERSAL/DISNEY/CONVENTION CENTER

PaolaRating, 5 stars2 weeks ago

Great place! Close to everything, Son is a great host! We really enjoyed our holidays

4.9 out of 5 average rating, 123 reviews

The Point Hotel & Suites - 705H Luxury - Pool View

RobertoRating, 5 stars3 months ago

Very good location for amusement parks. I would stay there again!

4.9 out of 5 average rating, 265 reviews

Condo in Orlando

Vista Cay Orlando Lakeview Condo

JamesRating, 5 stars5 days ago

Excellent spacious apartment! everything you could possibly need was in the room! Was a shame the main clubhouse pool was undergoing renovation but not much we can do about that! Thoroughly enjoyed the stay and would recommend to anyone going! There is building work being carried out opposite however the noise was low and was during the day when we were out and about! perfect location close to all the parks!