Vacation rentals with a pool in Wildwood

Find and book unique homes with a pool on Airbnb

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Popular amenities for Wildwood rentals with a pool

House rentals with a pool

Top guest favorite
Home in The Villages
5 out of 5 average rating, 34 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

TammyRating, 5 stars1 month ago
I’ve stayed at a few Airbnb’s, this was BY FAR the most comfortable one yet!! Honestly, we all felt so at home and settled in~it was perfect! The neighbors were friendly, the golf cart was great!! The town squares were a blast! We would 100% rent this exact home again. Actually, one of my sisters already did for this fall! Dean & Sheila always responded quickly with any questions I had. I can’t say enough good on how perfect this was!!!!!!!!
Guest favorite
Home in The Villages
5 out of 5 average rating, 17 reviews

Heated Pool, Dog Friendly, Golf Cart Included

YolondaRating, 5 stars4 weeks ago
Everything was perfect, beyond expectations! Very nice and responsive hosts, definitely would to love visit again!
Top guest favorite
Home in Wildwood
4.97 out of 5 average rating, 73 reviews

New home in the new part of the villages.

KasieRating, 5 stars1 month ago
Nice and clean place! Would stay again.
Top guest favorite
Home in The Villages
4.94 out of 5 average rating, 36 reviews

The Sunshine Retreat with Golf Car

JosephRating, 5 stars1 day ago
We enjoyed Kym's place. Conveniently located to Sawgrass. Enjoyed nightly live music. Enjoyed the front screened in porch in the evenings! Great host, would recommend to book Kym's place!
Top guest favorite
Home in Sumterville
5 out of 5 average rating, 13 reviews

The Golfer's Edge

RuthRating, 5 stars1 week ago
We came to visit family again and were thrilled to see that the same Airbnb (Rachel’s) we stayed at before was available. The description is very accurate—truly a five-star home!
Superhost
Home in The Villages
5 out of 5 average rating, 4 reviews

The Villages, Heated Pool Walk to Sawgrass

MistiRating, 5 stars1 week ago
I can’t say enough about this place or the host!! It was way more than I ever expected. We were able to check in sooner than the original check in time. Dave was awesome with communication and periodically checked in to make sure everything was going good throughout our stay. Everything was well stocked in the house from the kitchen (including spices and other little stuff that you would normally have to run out and buy to make a meal) to the bathrooms. There is everything you would need for the pool also. Dave even thought about your furry friends by providing leashes/bowls and treats. The house was immaculate! All you needed to do was literally pack your bags. Thanks for a great stay. We hope to return to the villages in the winter time!
Guest favorite
Home in Ocala
4.85 out of 5 average rating, 72 reviews

Elegant Ocala Oasis w/Pool: Unwind in Luxury

JamesRating, 5 stars2 weeks ago
Host was helpful and responsive, home close to a lot of restaurants and grocery stores. House was clean and did what we needed it to do for my family, no complaints and would definitely book again.
Top guest favorite
Home in The Villages
5 out of 5 average rating, 15 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

MichaelRating, 5 stars1 week ago
Place was extremely clean Robert got back with a response within a few minutes I asked Robert about the area and he described it perfectly, just where I wanted to stay. Close to Brownwood, Deluna Pool and Edna's on the Green Also Close to rt.301 and 75. Robert is a 10 Star Superhost!!

Condo rentals with a pool

Guest favorite
Condo in Florida Center
4.88 out of 5 average rating, 225 reviews

Maria Luz Studio-Huge Terrace/Universal area.

LisaRating, 5 stars2 weeks ago
Fantastic and Wonderful! This place has by far been the best!
Superhost
Condo in Crystal River
4.84 out of 5 average rating, 161 reviews

Crystal River Bungalow with boat slip

WilliamRating, 5 stars3 weeks ago
The property was well maintained. While it was some distance from town, it was helpful to have GPS for directions. The house was comfortably appointed and nicely decorated. It was well equipped with all necessities. The stacking washer and dryer was particularly useful and easy to use. The spiral staircase to the upstairs bedroom, however, could be a challenge for some folks. All in all, a good property, attentive host, and a good stay.
Guest favorite
Condo in Kissimmee
4.79 out of 5 average rating, 187 reviews

Mickey's Retreat(K2)

JackRating, 5 stars1 month ago
Stayed at Celso’s apartment for 2-weeks. It was a great size for 2 people and an ideal location for those looking to do the Disney and Universal parks. Apartment is just a short drive away from plenty of shops, restaurants and fast food places. It also has a 24h petrol (gas) station just outside of the complex which is really convenient. Overall, really enjoyed our stay the complex is really nice and feels very welcoming. Would highly recommend for two people. Celso was a great host, super responsive to any messages and helpful with any questions we had during our stay. One minor downside, not to the fault of Celso or his apartment, but the complex had a nesting hawk during our stay. This was no issue for 95% of our stay, but did swoop at us once. Would advise being cautious when walking to the car park, especially with young children.
Superhost
Condo in Four Corners
4.72 out of 5 average rating, 120 reviews

No BNB fees -Oasis Condo 5 min to Disney

SoniaRating, 5 stars2 weeks ago
Very beautiful location, calm surroundings and very close to all attractions
Top guest favorite
Condo in Orlando
5 out of 5 average rating, 143 reviews

Disney & Epic Free Shuttle, Kitchen

ShelleyRating, 5 stars3 days ago
Ryan's place was awesome! It was convenient to everything nearby as well as suited all of our needs. Ryan was a great host as he was quick to respond to anything we had questions about. I'd definitely stay here again! 10/10 for sure!!!!
Top guest favorite
Condo in Crystal River
4.99 out of 5 average rating, 117 reviews

Waterfront Condo in Sawgrass Landing

JustinRating, 5 stars2 weeks ago
Great place to stay! Beautiful views and clean place!
Superhost
Condo in Davenport
4.84 out of 5 average rating, 171 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

AngelRating, 5 stars2 weeks ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
Superhost
Condo in Kissimmee
4.77 out of 5 average rating, 126 reviews

1-101 Legacy Dunes, Gym, Tennis, Close To Disney!

ValentinaRating, 5 stars1 month ago
I had a great stay! The place was clean, comfortable, and just as described. The host was very friendly and responsive, which made everything super easy. I’d definitely stay here again!

Home rentals with a private pool

Villa in Four Corners
4.33 out of 5 average rating, 3 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

AurianaRating, 5 stars6 months ago
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.
Home in Ocala
New place to stay

Designer Pet-Friendly Retreat with Heated Pool

AngieRating, 5 stars2 weeks ago
very clean and roomy! great hosts! big yard. Will be back for sure!
Superhost
Home in Davenport
4.95 out of 5 average rating, 115 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

RachelRating, 5 stars1 month ago
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.
Home in Inverness

Family Villa Bettina - Recently Remodeled

ChuckRating, 5 stars60 months ago
Very clean, well appointed space. The pool is great.
Villa in Kissimmee
4.79 out of 5 average rating, 252 reviews

Visit Disney World from a Sunny Home with a Pool

AngelaRating, 5 stars1 month ago
Home was beautiful! area was quite and close by of of attractions and restaurants. Only thing I advise is bringing extra wash towels, they are not provided. We went to Walmart which is literally right around the corner.
Guest favorite
Villa in Kissimmee
4.92 out of 5 average rating, 50 reviews

Family Retreat Near Disney with Pool & Hot Tub!

JenniferRating, 5 stars1 week ago
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location
Home in Kissimmee
4.82 out of 5 average rating, 17 reviews

Sleeps 20! Near Disney w/ Pool | Twice-as-Nice

KimberlyRating, 5 stars2 months ago
Place was nice. It had a lot of amenities that we enjoyed. The game room and pool table was fantastic. Rooms were nice and comfortable. Would definitely stay again.
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

TarahRating, 5 stars1 week ago
The home was beautiful & exactly as described.

Quick stats about vacation rentals with a pool in Wildwood

  • Total rentals

    370 properties

  • Nightly prices starting at

    G$8,363 GYD before taxes and fees

  • Total number of reviews

    6.9K reviews

  • Family-friendly rentals

    330 properties are a good fit for families

  • Pet-friendly rentals

    150 properties allow pets

  • Rentals with dedicated workspaces

    220 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sumter County
  5. Wildwood
  6. Rentals with pools