
Holiday rentals with a pool in Wildwood
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wildwood
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Wildwood rentals with a pool
House rentals with a pool

Villa la Bella
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.

Pool Home Great Location 3/2 & 2 Golf Carts
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!!!!!!!!

Vacation home in The Villages
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!

The Villages with a View
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.

The Villages - Sunshine and pickleball
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!

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

The Sunshine Retreat with Golf Car
Great home and great hosts. Highly recommend!

The Villages, Heated Pool Walk to Sawgrass
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

Studio near Universal Studios with great view
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!

Near Disney/Universal Lovely 2bedroom/2bath Condo
The place was great! it was perfect for a quick family trip to Disney. Would highly recommend!

Maria Luz Studio-Huge Terrace/Universal area.
Fantastic and Wonderful! This place has by far been the best!

Crystal River Bungalow with boat slip
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.

No BNB fees -Oasis Condo 5 min to Disney
Very beautiful location, calm surroundings and very close to all attractions

Cheery 2BR Condo w/zero entry pool near Disney
very cozy private location with lots of stores within 5 mins. beach accessories available for convenience. will book again.

Waterfront Condo in Sawgrass Landing
Great place to stay! Beautiful views and clean place!

Full-Service Gated Resort, Disney, Universal, MCO!
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
Home rentals with a private pool

Disney's Championsgate: Private Pool & Arcade Fun!
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.

Designer Pet-Friendly Retreat with Heated Pool
very clean and roomy! great hosts! big yard. Will be back for sure!

Airy, Stylish Home with Pool Heat Included in Davenport
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.

Family Villa Bettina - Recently Remodeled
Very clean, well appointed space. The pool is great.

Visit Disney World from a Sunny Home with a Pool
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!

Family Retreat Near Disney with Pool & Hot Tub!
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

Sleeps 16! Pool + Arcade | Orlando Resort Retreat
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.

Private Oasis with Pool & Spa- 3400clr
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
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Kissimmee Holiday rentals
- Central Florida Holiday rentals
- Tampa Holiday rentals
- Tampa Bay Holiday rentals
- St Petersburg Holiday rentals
- Seminole Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Rentals with a hot tub Wildwood
- Family-friendly rentals Wildwood
- Rentals with a firepit Wildwood
- Pet-friendly rentals Wildwood
- Villa rentals Wildwood
- Rentals with breakfast Wildwood
- House rentals Wildwood
- Apartment rentals Wildwood
- Fitness-friendly rentals Wildwood
- Rentals with a washing machine and dryer Wildwood
- Flat rentals Wildwood
- Rentals with a fireplace Wildwood
- Rentals with a cinema Wildwood
- Cottage rentals Wildwood
- Rentals with lake access Wildwood
- Rentals with outdoor seating Wildwood
- Beachfront rentals Wildwood
- Waterfront rentals Wildwood
- Rentals with a patio Wildwood
- Family-friendly rentals Wildwood
- Rentals with pools Sumter County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Universal Studios Florida
- Orange County Convention Center
- Weeki Wachee Springs
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- Rainbow Springs State Park
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Walt Disney World Resort Golf
- Island H2O Water Park
- Blue Spring State Park
- ICON Park
- Universal CityWalk