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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

Nov 25 – Dec 2

G$20,585 GYD per night

Condo in Orlando

4.89 out of 5 average rating, 327 reviews

FantasticView, 1 BR/2BA, 1 MILE TO DISNEY-Sleeps 6

Located 1 mile to Disney Springs in a Gated-Community A NEWLY REFURBISHED Spacious 1-bedroom, 2-bath Condo in Lakefront luxury @ Blue Heron Beach Resort nestled on shores of 400+ acre Lake Bryan, 2 blocks off I4 @ Lake Buena Vista exit. This luxurious condo overlooks the Pool & Lake Bryan. Sleeps 6 It’s all here! The ultimate Walt Disney World vacation right here at your fingertips! From the best of Disney or Work Travel this property offers the perfect environment to spend a lifelong memory

Nov 23 – 30

G$26,580 GYD per night

Guest suite in Orlando

4.99 out of 5 average rating, 124 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

G$17,820 GYD 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

2:2 2nd floor Condo behind Publix in Lake Cay Shopping Center 3/4 mile from Convention Center and right across from Shingle Creek Resort. 1.25 miles to Hilton; 1.5 miles to Hyatt; 1 mi SeaWorld; 3 mi Universal; 6 mi Disney; 3.5 mi Universal; 1 mi Orlando Eye sits beside Little Lake Cay - pool across from parking and hottub. Walk to Larger Lake Cay and over to the Large Amenity Center of the Resort community which has a gym and large pools. 8 miles to OIA. Highly sought after location pixotw

Sep 24 – Oct 1

G$28,201 GYD 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

G$23,072 GYD 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

G$21,838 GYD 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 11 – 18

G$30,689 GYD 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

G$17,403 GYD 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.

Aug 5 – 12

G$22,357 GYD 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

G$18,365 GYD 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

G$25,761 GYD per night

Guest suite in Orlando

4.97 out of 5 average rating, 383 reviews

Vacation & Oasis Mood with #1 location - Pool

From our family to you, we are welcoming you in our Home into our private Orlando, Florida, Oasis :-) Located a very short commute to some of the world most famous tourist attraction, Disney & Universal studio to the privacy of our fully equipped Guest area. We want to make sure that your stay to our home will be memorable and we want to see you again :-)

Jun 29 – Jul 6

G$27,943 GYD per night

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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 Kissimmee

4.79 out of 5 average rating, 256 reviews

3 bedroom Orlando Florida pool home

Dec 10 – 17

G$25,341 GYD 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

G$30,940 GYD per night

Home in Kissimmee

4.9 out of 5 average rating, 294 reviews

Family Home minutes from Disney!

Aug 2 – 9

G$25,904 GYD per night

Home in Kissimmee

4.97 out of 5 average rating, 111 reviews

Magical home! 15 minutes from all parks!

Feb 8 – 15

G$23,047 GYD per night

Home in Kissimmee

4.88 out of 5 average rating, 108 reviews

No Airbnb Fee! Thematic Rooms w/ Pvt Pool °o° Area

Aug 24 – 29

G$25,075 GYD per night

Home in Kissimmee

4.8 out of 5 average rating, 167 reviews

4 Bedroom House Heated Pool 20 min From All Parks

Aug 2 – 9

G$34,650 GYD per night

Home in Kissimmee

4.84 out of 5 average rating, 205 reviews

3 bedroom Villa in Kissimmee

Jun 28 – Jul 5

G$30,842 GYD per night

Home in Orlando

4.79 out of 5 average rating, 120 reviews

Private Home w/ Pool/3 Bd 2 Bath/Close to Disney

Oct 12 – 19

G$35,205 GYD per night

Condo rentals with a pool

Condo in Orlando

4.9 out of 5 average rating, 128 reviews

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

May 28 – Jun 4

G$27,183 GYD per night

Condo in Orlando

4.81 out of 5 average rating, 342 reviews

Luxury Apt on I-Drive & view of Universal Orlando

Oct 17 – 24

G$17,401 GYD per night

Condo in Orlando

4.89 out of 5 average rating, 109 reviews

VCR1-303 Deluxe Condo - Near Major Attractions

Sep 23 – 30

G$33,608 GYD per night

Condo in Orlando

4.87 out of 5 average rating, 200 reviews

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

Jul 27 – Aug 3

G$29,312 GYD per night

Condo in Kissimmee

4.98 out of 5 average rating, 289 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Aug 30 – Sep 6

G$26,952 GYD per night

Condo in Kissimmee

4.95 out of 5 average rating, 177 reviews

BRAND NEW CONDO- 2 BR 2 Bath-Great location!

May 16 – 23

G$30,245 GYD per night

Condo in Kissimmee

4.91 out of 5 average rating, 110 reviews

Modern Storey Lake Resort Disney Orlando 3171-206

Sep 30 – Oct 7

G$29,724 GYD per night

Condo in Orlando

4.97 out of 5 average rating, 295 reviews

Luxurious Waterfront Resort near Disney &Universal

Aug 31 – Sep 7

G$36,174 GYD 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

G$29,963 GYD 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

G$73,577 GYD per night

Villa in Kissimmee

5.0 out of 5 average rating, 13 reviews

Family Retreat Near Disney with Pool & Hot Tub!

Nov 26 – Dec 3

G$70,277 GYD per night

Home in Davenport

4.97 out of 5 average rating, 97 reviews

Airy, Stylish Home with Pool Heat Included in Davenport

Mar 22 – 29

G$68,964 GYD 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

G$36,473 GYD per night

Home in Davenport

4.61 out of 5 average rating, 23 reviews

Solterra Resort 7br Family Home Pool Near Disney

Nov 14 – 21

G$54,198 GYD per night

Home in Davenport

4.75 out of 5 average rating, 4 reviews

Luxurious 8br Palms Villa Pool Home-Champions Gate

Dec 11 – 18

G$93,816 GYD per night

Villa in Davenport

4.67 out of 5 average rating, 6 reviews

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

Oct 26 – Nov 2

G$145,758 GYD 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
G$4,179 GYD before taxes and fees

Destinations to explore