Holiday 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 favourite
Home in The Villages
4.91 out of 5 average rating, 70 reviews

Villa la Bella

TerryRating, 5 stars2 weeks ago
We can’t say enough great things about this villa and our host Eric. He was available to answer questions throughout our stay and gave great information before we arrived. Extremely helpful guide❤️ We would very much recommend this villa and the villages as a destination. So much fun. Such great people.
Top guest favourite
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!!!!!!!!
Top guest favourite
Home in The Villages
5 out of 5 average rating, 15 reviews

Vacation home in The Villages

RyanRating, 5 stars1 month ago
Marty was very responsive and accommodating! My entire family enjoyed our stay and the house was perfect for everyone's needs! Would definitely recommend for anyone looking to visit The Villages!
Guest favourite
Home in The Villages
4.83 out of 5 average rating, 6 reviews

The Villages with a View

JeffreyRating, 5 stars3 weeks ago
We came down to The Villages looking for a retirement home. The house was everything we wanted and needed for our stay. They thought of everything… Just bring your bags, everything else is here. GREAT LOCATION, CONVENIENT TO EVERYTHING !!! Jeffrey & Becky K.
Top guest favourite
Home in Wildwood
4.93 out of 5 average rating, 15 reviews

The Villages - Sunshine and pickleball

RachelRating, 5 stars2 weeks ago
We had a great stay at this house! There is so much to do in the area from bowling to movies and tons of great restaurants. It was a perfect location to Lake Harris as well. The house was spotless and had everything we needed for a wonderful stay!
Top guest favourite
Home in The Villages
4.94 out of 5 average rating, 72 reviews

Golf Cart, King Bed, Small Dogs, and Water System!

AnnRating, 5 stars3 weeks ago
1000 words isnt enough . so warming and relaxing home. so much to do. book at least 10 days 7 is not enough . u will have memories that will draw you back. . This home exceeds any home i ever rented. around every bend on the golf cart paths you will find anouther bend of fun that goes on and on.... if u are craving a fast food for a quick bite to eat, where else can u go thru drive thru on a golf cart !
Top guest favourite
Home in The Villages
4.94 out of 5 average rating, 35 reviews

The Sunshine Retreat with Golf Car

MikeRating, 5 stars1 week ago
Great home and great hosts. Highly recommend!
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!

Apartment rentals with a pool

Guest favourite
Apartment in Florida Center
4.9 out of 5 average rating, 111 reviews

Studio near Universal Studios with great view

KinjalRating, 5 stars4 days ago
The apartment BNB was really great and exactly as described with all basic amenities provided. Super close, walkable distance, to a variety of restaurants with different cuisines. Universal Studios is a close 10 mins drive/uber ride away. The studio feels super cozy, the view from the balcony is also very nice. Laundry room is right next to the unit which was very convenient. Hosts are quick to respond to any messages/questions you may have. Enjoyed my time at this Airbnb!
Guest favourite
Apartment in Kissimmee
4.87 out of 5 average rating, 134 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

KassidyRating, 5 stars1 week ago
The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!
Guest favourite
Apartment 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
Apartment in Crystal River
4.84 out of 5 average rating, 161 reviews

Crystal River Bungalow with boat slip

WilliamRating, 5 stars2 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.
Superhost
Apartment 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
Guest favourite
Apartment in Kissimmee
4.9 out of 5 average rating, 149 reviews

Cheery 2BR Condo w/zero entry pool near Disney

MindyRating, 5 stars2 weeks ago
very cozy private location with lots of stores within 5 mins. beach accessories available for convenience. will book again.
Top guest favourite
Apartment 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
Apartment in Davenport
4.84 out of 5 average rating, 170 reviews

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

AngelRating, 5 stars1 week ago
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend

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 stars1 week 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, 251 reviews

Visit Disney World from a Sunny Home with a Pool

ClaudiaRating, 5 stars1 month ago
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!
Guest favourite
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 Davenport
4.83 out of 5 average rating, 48 reviews

Sleeps 16! Pool + Arcade | Orlando Resort Retreat

MindyRating, 5 stars2 weeks ago
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.
Home in Kissimmee

Private Oasis with Pool & Spa- 3400clr

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

Quick stats about holiday rentals with a pool in Wildwood

  • Total rentals

    370 properties

  • Nightly prices starting at

    ₹3,455 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