Vacation Rentals & Apartments in Charleston

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7,180 apartments

⭐Great Value Villa w/ Private Pool - Nearby Disney Resort⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$265

Beachway Per Ankh - **Private Heated Pool Minutes From The Beach**

Pompano Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$373

Unique 5 Star Home - Private Pool, Free SOLAR Pool heat, WIFI, BBQ, Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Violet lane” Home was clean and charming.We enjoyed the pool and privacy greatly. Owner thought of most anything we may need, except one; toilet paper. This was our first time staying in a private home rather than a hotel so perhaps it isn’t a given but if we had known, it would have saved us an immediate trip to store. I cannot speak for other guests but felt that not starting laundry, despite stating was not mandatory, not doing so may affect my deposit. A few other minor issues: missing ping pong table, “key?” to working slot machines, how, or if, the ice maker worked and where the garage door opener was located(we did find on the furnace in the garage the day before we left), and whether the swinging chair was safe to use, despite the crack, may have been problems easily remedied with a phone call but ultimately not important enough to bother owner and take time away from us. Not meant to be a negative review, it is not. Overall, we had a lovely time and would stay again. However, it seemed important to be honest in regard to our experience.

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$149

⭐ Spacious and Comfortable Villa - Near Theme Parks ⭐

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

“Fantastic Stay” The home was in a beautiful community and there was a huge resort pool with all the things one would look for in a resort setting. The home itself was immaculate and very clean upon arrival. The beds were all comfortable and the rooms were spacious. We enjoyed the home and the resort so much that we actually spent a few days less at the parks. The reservation process was simple and straightforward. All in all a great vacation!

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$265

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$177

⭐ Spacious 8 Bedrooms Champions Gate Resort Villa w/ Private Pool ⭐

Davenport villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$401

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

All filters match

Price per night from

$401

⭐ 6 Bedrooms 5 Bathrooms Villa - Great Deal! - Near Disney World ⭐

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$265

⭐Good Location for Theme Parks - Spacious 7 Bedrooms Villa⭐

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$265

Emerald Island Villa,3 mi to Disney,Water View,4BedRm/3Bath,Gap Discount,Pool

Four Corners villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$171

Highgate Park Villa with private swimming pool, close to Disney, sleeps 9.

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 37 minutes

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$212

Oakhill Disney Villa

Kissimmee villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$214

Home Away Villa

Davenport house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$229

8164 Windsor Palms Resort

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$149

Lake View Charmer l Private Pool l Pets l Disney

Buena Ventura Lakes house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$229

Spacious Fun Tampa Haven: Games | Pool | 7-15 min From Everything

Carrollwood house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

Match: Private outdoor pool (unheated) Swing set or jungle gym Wheelchair accessible

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Price per night from

$573

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Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$77

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$144

DC. Baltimore. Annapolis *Suite in on the main fl.

Highland apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$115

Charming Townhouse ✨ 2 King Suites ✨ 10 Mins to Disney ✨ Free Parking

Orlando townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$229

Minutes From Disney 4BR/3BA At Regal Palms

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$172

Steps to the Beach! Beautiful Resort!

Hilton Head condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$202

RELAX or HAVE FUN: 2 bed condo (walk to beach)

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect Mother's Day Weekend with my son” The location was only two blocks from the beach and has two pools onsite. The condo has everything you need to make your stay comfortable, there was even an infant float sun canopy that we used for our 18 month old grandson. It is also very conveniently located to multiple excellent shops and restaurants.

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$115

Beautiful Studio Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$156

Beautifully renovated Venetian Bay Townhouse close to Disney

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$166

Spacious House by Beach, AFB, Stores & more

Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$343

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

St. Michaels house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Responds fast! avg. 38 minutes

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$2,290

Luxury Waterfront - 40 Acre Estate - Swimming, Boating, Activities

Royal Oak manor house

  • 25 bedrooms
  • 25 bathrooms
  • sleeps 50

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$7,443

BHS Vacation Homes In Summerville Resort minutes away to Disney Park’s

Celebration house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$137

BEST PARADAISE ORLANDO

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$264

Responds fast! avg. 54 minutes

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$267

Fairfield Glade 2 Bedroom Deluxe

Fairfield Glade villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 32 minutes

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$144

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$328

Condo in Naples Bay Resort - Close to 5th Ave

Naples condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$344

Disney World 2 Miles

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$136

Luxury Cottage!

Mobile cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 33 minutes

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$228

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$630

Ocean view with balcony quiet top floor!

Surfside Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

2 of 3 match: Private outdoor pool (unheated), Swing set or jungle gym, Wheelchair accessible

2 of 3 filters match

Price per night from

$287

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