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Vacation rentals with a pool in Williamsburg

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Williamsburg

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest suite in Orlando

4.85 out of 5 average rating, 106 reviews

✨️Modern Suite with POOL- Close to All Parks!🎡

This brand new beautiful studio with a POOL! is located in Skylake Orlando, a safe and fun neighborhood surrounded by a variety of great restaurants, shops, malls, but most of all close to ALL the parks. 9 min to Sea World, 7 min to Aquatica, 13 min to Disney World, 13 min to Universal Studios and many more fun places to visit. The studio is perfect for 2, it has a laundry, luxurious bathroom and a fully equipped kitchenette. You will also have access to a gorgeous pool and grill in the backyard

Apr 1 – 8

R2,003 ZAR per night

Guest suite in Orlando

4.99 out of 5 average rating, 123 reviews

Beautiful studio with pool & close to attractions!

An amazing studio space, attached to the main home, with private entrance, King size bed, full bath, and kitchenette. Recently renovated and very comfortable. New Mitsubishi mini-split AC system and a Nespresso Machine for your morning coffee. Access to pool area, gazebo, and washer/dryer outside! Centrally located: under 20 minutes to the airport, 5 minutes to Florida Mall, 10 minutes to Mall at Millenia, under 20 minutes to Universal Studios, 35 minutes to Disney, and 10 minutes to Downtown!

Oct 12 – 19

R1,667 ZAR per night

Guesthouse in Orlando

4.94 out of 5 average rating, 212 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. Pool & Spa available (Not Shared) All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

Dec 26 – Jan 2

R2,125 ZAR per night

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA

Parking & resort fees included. An Orlando Adventure with All the Extras. Star Island, a 5 star resort located Just 10 minutes from Walt Disney World®, offers so many fun on-site amenities and activities, it actually rivals the magic of Orlando itself. Enjoy the resort at a fraction of the cost of the parks. 2 pools, SPA's, Fitness center, Golf-Driving range, Tennis Courts, Basketball Courts, Pickle Ball courts, Volleyball courts, Water sports, Pool Bar, Ping Pong, Game Room.

May 1 – 8

R2,008 ZAR per night

Guest suite in Orlando

4.99 out of 5 average rating, 243 reviews

Location, Location, Location near all attractions

This is a poolside in-law apartment with a full kitchen, bedroom, full bath and a living room located in a quiet, residential neighborhood in an upper scale part of town. It has a king size bed & will accommodate 2 adults comfortably. This in-law apartment is an addition that was built onto the back of our home. It is completely closed off from the our main house and has it's own main entrance so it is private. So, you will have the apartment all to yourselves.

Oct 10 – 17

R2,821 ZAR per night

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

A full cottage for 4! The perfect place stay. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check out unit We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other.

Dec 4 – 11

R1,602 ZAR per night

Guest suite in Orlando

4.99 out of 5 average rating, 339 reviews

Sunny Resort Style - Pool & central location ☀️

Resort Style Vacation with much more Privacy ? You found the right place! :-) From our family to you, we are welcoming you into your modern & efficient Airbnb Guest suite! :-) Located a very short commute to some of the world's most famous tourist attraction, Disney & Universal studio & to an amazing oasis style backyard offered to you! We want to make sure that your stay to our home will be memorable and we want to see you again :-)

Oct 1 – 8

R2,366 ZAR per night

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

Jul 28 – Aug 4

R2,032 ZAR per night

Guesthouse in Orlando

4.99 out of 5 average rating, 143 reviews

Quaint Guesthouse Near the Attractions

This picturesque hideaway suite is recently remodeled with granite and tile throughout. Ideal for couples, but can comfortably accommodate up to a family of four with a separate king size bedroom plus a king size sleeper sofa in living room. You may choose to prepare meals in the kitchenette, use the BBQ grill, dine in one of the hundreds of nearby restaurants, or order Uber Eats if you prefer to stay home and relax.

Oct 6 – 13

R2,060 ZAR per night

Guest suite in Orlando

4.96 out of 5 average rating, 167 reviews

Flor de María beautiful and relaxing GUEST ROOM ☘️☘️

Nice and relaxed Guest room with King side bed!! Our beautiful studio is attached to our house. With entrance and bathroom private. Parking included. You can enjoy areas like pool, grill and fireplace (These areas are shared) Our Space is only for 2 adults. Sorry!!! We not accepting kid’s, baby’s or pest. We are sure!!! You will love our place!!! We offer faster WiFi and Nexflix!!!

Aug 26 – Sep 2

R1,689 ZAR per night

Apartment in Orlando

4.98 out of 5 average rating, 137 reviews

Entire Lovely & Cozy Centrally Located Place

Enjoy a comfortable experience at this centrally-located place it is Close to Disney, Seaworld, Universal, shopping and Restaurants. Large spacious 1 BR/BA unit 1 Queen size bed and Queen Sofa bed, Access to Entire apartment, Full Kitchen, amenities Swimming Pool and Fitness Center Including free high speed WIFI, cable , Roku, Netflix and Free parking

Jul 24 – 31

R2,367 ZAR per night

Condo in Orlando

4.87 out of 5 average rating, 167 reviews

Beautiful Lakeview ★ 1 Mile to Disney ★ 1BDR/2BA

Nestled in the heart of Disney, this condo will accommodate a memorable stay. Amazing location! Right by Disney. Beautiful Lakeview! Within a few miles to: - Disney (Less than 1 mile) - Seaworld (5 miles) - Convention Center (6 miles) - Universal Studios (8 miles) - Orlando Airport (16 miles)

May 21 – 28

R2,001 ZAR per night

Vacation rentals for every style

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Popular amenities for Williamsburg rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Orlando

4.81 out of 5 average rating, 147 reviews

Perfect location near Sea World and Disney

Oct 18 – 25

R3,118 ZAR per night

Home in Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

Dec 14 – 21

R2,302 ZAR per night

Home in Kissimmee

4.9 out of 5 average rating, 294 reviews

Family Home minutes from Disney!

Aug 24 – 31

R2,257 ZAR per night

Home in Kissimmee

4.97 out of 5 average rating, 111 reviews

Magical home! 15 minutes from all parks!

Sep 8 – 15

R2,124 ZAR per night

Home in Kissimmee

4.92 out of 5 average rating, 125 reviews

South Facing Pool Home! 5 Miles from Disney

May 10 – 17

R3,086 ZAR per night

Home in Kissimmee

4.8 out of 5 average rating, 167 reviews

4 Bedroom House Heated Pool 20 min From All Parks

Nov 15 – 22

R3,188 ZAR per night

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

Jun 28 – Jul 5

R2,837 ZAR per night

Home in Orlando

4.91 out of 5 average rating, 117 reviews

Lakefront presidential suite / resort pool

May 14 – 21

R2,689 ZAR per night

Condo rentals with a pool

Condo in Orlando

4.81 out of 5 average rating, 342 reviews

Luxury Apt on I-Drive & view of Universal Orlando

Oct 17 – 24

R1,600 ZAR per night

Condo in Orlando

4.85 out of 5 average rating, 245 reviews

BreathtakingView-1BR/2BA-1 MILE TO DISNEY-Sleeps 6

Nov 23 – 30

R2,751 ZAR per night

Condo in Orlando

4.9 out of 5 average rating, 128 reviews

[Lake View, Modern Decor, 1 Mile to Disney!]

May 28 – Jun 4

R2,684 ZAR per night

Condo in Orlando

4.86 out of 5 average rating, 199 reviews

Airbnb's Choice- Best at Blue Heron- Stunning View

Jul 27 – Aug 3

R2,696 ZAR per night

Condo in Kissimmee

4.98 out of 5 average rating, 288 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Apr 3 – 10

R2,552 ZAR per night

Condo in Orlando

4.91 out of 5 average rating, 405 reviews

Cozy Cay Condo Convn Ctr Vista Cay 2BR 2Ba 4 bds

Sep 11 – 18

R3,327 ZAR per night

Condo in Orlando

4.95 out of 5 average rating, 101 reviews

Top Floor*Balcony*VistaCay Convention Ctr & iDrive

May 17 – 24

R2,483 ZAR per night

Condo in Orlando

4.86 out of 5 average rating, 118 reviews

Gorgeous 1 Bed 2 Bath Condo just 1 mile to Disney

Dec 6 – 13

R2,517 ZAR per night

Home rentals with a private pool

Townhouse in Kissimmee

4.83 out of 5 average rating, 191 reviews

Beach House with Private Pool and Clubhouse near Disney

Aug 22 – 29

R2,697 ZAR per night

Townhouse in Kissimmee

4.88 out of 5 average rating, 128 reviews

Stellar Five Bedroom Townhome Under Ten Minutes to Disney

Nov 3 – 10

R6,803 ZAR per night

Villa in Kissimmee

5.0 out of 5 average rating, 13 reviews

Family Retreat Near Disney with Pool & Hot Tub!

Mar 16 – 23

R6,320 ZAR per night

Home in Davenport

4.97 out of 5 average rating, 97 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Feb 9 – 16

R4,585 ZAR per night

Villa in Kissimmee

4.79 out of 5 average rating, 223 reviews

Visit Disney World from a Sunny Home with a Pool

Dec 9 – 16

R3,360 ZAR per night

Home in Davenport

4.61 out of 5 average rating, 23 reviews

Solterra Resort 7br Family Home Pool Near Disney

Aug 28 – Sep 4

R4,452 ZAR per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

Jun 21 – 28

R8,094 ZAR per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

Amazing Dream Solterra Villa -Disney/club/pool/spa

Sep 11 – 18

R12,183 ZAR per night

Quick stats about vacation rentals with a pool in Williamsburg

Total rentals
530 properties
Rentals with dedicated workspaces
280 properties have a dedicated workspace
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
330 properties are a good fit for families
Total number of reviews
17K reviews
Nightly prices starting at
R376 ZAR before taxes and fees

Destinations to explore