Vacation Rentals & Apartments in Charleston

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39,466 apartments

From $80/nt,4br/3ba townhome with hot tub/lake view,Near Disney,Seaworld

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 16 minutes

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$103

❤️ Capture Those Magical Memories ❤️ Peaceful Lakeside Haven

Kissimmee house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 20 minutes

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$189

Immaculate, Minutes to Disney, Great Amenities!

Kissimmee apartment

3 bedrooms / 2 bathrooms / sleeps 8

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$109

Woodstone at Massanutten

Massanutten apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 27 minutes

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$161

Luxury Cabin at Shenandoah Crossing Resort

Shenandoah log cabin

2 bedrooms / 2 bathrooms / sleeps 6

“Great time with the kids.” We had a wonderful time with four kids. There are many on site activities during the winter. Some are no charge like swimming, mini golf and various sports. Others like the horses are very reasonably priced. The cabin was clean comfortable & kid friendly! Also was very conveniently located to go to Shenandoah Ntl Park for hiking and Massanutten for snow tubing Hillel Baron

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$114

$80/nt,4BR 1900sqft townhome,lake view,Near Disney,Seaworld,Convention Center

Kissimmee apartment

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 16 minutes

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

All filters match

Price per night from

$103

Fantastic Vacation Home on Candy Palm Rd at Paradise Palms

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

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Price per night from

$135

Gorgeous Vacation Home with WiFi, on Yellow Lantana Ln

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 51 minutes

Match: Ceiling Fans Climbing frame Shared outdoor pool (heated) Games room Private fishing lake or river Fishing

All filters match

Price per night from

$159

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The Fountains

Orlando condo

2 bedrooms / 2 bathrooms / sleeps 6

5 of 6 match: Ceiling Fans, Fishing, Climbing frame, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$245

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 5

5 of 6 match: Climbing frame, Fishing, Ceiling Fans, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$101

#1 Location, BIG Mansion, 16 sleeps

Cary house

5 bedrooms / 6 bathrooms / sleeps 16

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$684

Bison Overlook Lodge on a 65 acre bison ranch

Maggie Valley log cabin

3 bedrooms / 2 bathrooms / sleeps 8

“Awe Inspired!” The cabin was wonderful. The Bison feeding was so much fun ,one of the Alpha males had such an assured look in his eyes it was almost regal. The bison burgers were to die first! While in the hotbed which is really nice BTW, we looked up and the sky looked like God himself filled the entire sky thick with glitter that's how many stars there were.When my dog went out here came the grey mini pony and my dog licked it's nose, I think they wanted to elope....LOL The Mtn Goats & Liamas were fun as well. We couldn't remember the last time we were so relaxed. We love Bison Overlook Lodge & we will be back!

Responds fast! avg. 2 hours 34 minutes

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$235

Tatonka Lodge - 2 master suites on a 65 acre bison ranch

Maggie Valley log cabin

4 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 2 hours 34 minutes

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$430

Fantastic Kissimmee Home and only 20 min

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 6

“Wonderful Townhouse” My husband and I stayed for 3 weeks in June/July. Townhouse is gorgeous and very comfortable. The community clubhouse was great. We loved using the pool almost daily. We were happily surprised to find added amenities in case you had children or grandchildren. TV control was tricky to figure out at first and shower water temperature can be inconsistent, but overall we had a marvelous stay and would definitely stay here again!

Responds fast! avg. 1 hour 42 minutes

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$64

The Retreat - Explore Disney & Florida in style

Kissimmee villa

4 bedrooms / 4 bathrooms / sleeps 10

“Wonderful Vacation Spot” The Retreat is a great place to stay with your family. The accommodations were well equipped, clean and a it's a great location. Brian is responsive and very nice to work with. I could not say anything bad about The Retreat.

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$172

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$453

Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 7 minutes

5 of 6 match: Games room, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Private fishing lake or river

5 of 6 filters match

Price per night from

$182

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

Siesta Key apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful and memorable vacation with our son,wife and grandchil” My husband and I rented unit B41,it was beautifull, tastefully decorated stainless steel appliances and new furniture. The owners thought of everything.Very pleased to have a washer and dryer in unit. The layout of this rental was spacious,the bed was very comfortable I slept like a baby which is rare when I'm away from home.The view of the intercostal water way and tropical landscaping were breathtaking whether relaxing in living room or dinning.It was very peaceful ,walking distance to Siesta keys famous beach and close to all amenities. Would recommend Bay Oaks!Thanks Barbara Okin.

Responds fast! avg. 2 hours 16 minutes

5 of 6 match: Climbing frame, Fishing, Ceiling Fans, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$143

Luxurious 5 Bedroom / 3 Bathroom Villa at Lake Berkley - Southern Exposure!

Kissimmee villa

5 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 28 minutes

5 of 6 match: Climbing frame, Fishing, Ceiling Fans, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$221

New Opening 5Br/3Ba Hot Tub/Lake View,Close Disney,Seaworld,Convention Center

Kissimmee townhouse

5 bedrooms / 3 bathrooms / sleeps 12

“Ok” Overall it was fine..checkout was at 11 and at 10 cleaners knocked on door and then preceded to sit in driveway waiting for us to leave. There was no dish soap or soap in bathrooms which would have been nice.

Responds fast! avg. 1 hour 16 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$114

Bahama Bay Resort and Spa

Four Corners condo

3 bedrooms / 2 bathrooms / sleeps 8

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$143

WELCOME TO PARADISE AT BAHAMA BAY.

Four Corners condo

3 bedrooms / 2 bathrooms / sleeps 8

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$131

2CLOSE TO ALL ATTRACTIONS! RESORT LUXURY LIVING ON A BUDGET!

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 24 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$217

OCEANFRONT Condo Unit Available March 29-April 5, 2020

Cocoa Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

4 of 6 match: Ceiling Fans, Private fishing lake or river, Fishing, Climbing frame, Shared outdoor pool (heated), Games room

4 of 6 filters match

Price per night from

$361

“A Classy Vacation Experience in any Season” My brother, who has problems walking, and I stayed at Sunnybank for a little under a week in the early spring when the Corolla horses are foaling. The layout of the well-appointed, three-storey main building was perfect for our needs: the fabulous view from the top floor living room provided the inspiration for him to walk up the grand stair case, and he could take the elevator when he was having problems walking. (There are two bedrooms with walk-in showers to accommodate people who have a problem walking.) It rained the first two days, which might have been gloomy any where else, but the library of videos, and stashes of games and playing cards gave us the opportunity to connect in ways that we hadn't since we were children. The fabulous cook's kitchen and multiple eating areas can accommodate a wedding party, family reunion, or any get away time one might want. Mine was a working vacation and the office there, which is outfitted with excellent Ethernet and WiFi connections plus a daybed for napping, was a better arrangement than my office at home. Comfort and casual, yet classy ambience abounds at Sunnybank. An excellent find!

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$571

Resort Vacation Townhouse / Resort Amenities / Private Pool / Windsor Palms

Four Corners townhouse

3 bedrooms / 3 bathrooms / sleeps 6

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$121

OCEAN VIEW FROM EVERY room and ROOM. FEW STEPS TO BEACH.

Hollywood apartment

2 bedrooms / 1 bathroom / sleeps 3

“Awesome View” We were met by Robert upon our late arrival. It's a suffifucient space for 2-3 adults. As described in the listing "Ocean view from every room and few steps to beach" . Beautiful/sunny weather and it rained only one day during our one week stay. Bed is comfortable and pillows and sheets are clean and nice too. It has air condition and, ceiling fan each in the living room and bedroom too. Internet works great! A parking is provided just downstairs at the entrance to the building. We walked on the boardwalk everyday. We loved shopping at the Sawgrass Factory Outlet! Many grocery stories are 5 min drive. Would stay at this place again. Thank you!

Responds fast! avg. 3 hours 32 minutes

4 of 6 match: Fishing, Games room, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Private fishing lake or river

4 of 6 filters match

Price per night from

$171

12 steps to the Beach; Florida Sun Coast Condo

St. Petersburg apartment

1 bedroom / 1 bathroom / sleeps 3

“Wonderful place” We arrived here and we're immediately enchanted with the location and view. The apartment is perfect for a couple and everything was in place, clean and with everything you need to start of a great vacation.

4 of 6 match: Fishing, Games room, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Private fishing lake or river

4 of 6 filters match

Price per night from

$115

XMAS AT DISNEY WORLD- 54 ACRE RESORT W/WATERPARK

Orlando hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

5 of 6 match: Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$285

❤️ Harry Potter Theme room Muggles will Love! Minutes to Disney ❤️

Kissimmee house

3 bedrooms / 2 bathrooms / sleeps 8

“Birthday Trip!” I do believe this might have been the funnest trip I've ever taken in my life. Having every single thing just minutes away from you was such a delight and such a pleasure to not have to drive around constantly in the car. This community is gated and seems like a really fun place to actually buy a vacation home. Actually, while we were there we looked into it and might be doing the same thing that this particular person is offering on TripAdvisor as well! First of all, the house was just absolutely amazing... Bigger than my own home even. It was just me, my son and my husband and our house was absolutely humongous. We actually had thought we would have another family with us but it fell through. Everything was clean and perfect. There were many things like dishwasher, laptop, printer, hair dryer, straightener, toiletries, food! When we arrived, we already had some basic needs that were furnished To Us by the owners. It was such a treat to see that they really cared about us to furnish those things! There was a perfect screened in porch out the back over looking a little bit of a water marsh where we got to watch the birds everyday. The wildlife in our particular yard was extremely delightful. From frogs to lizards two birds two cranes we had an amazing time when we were relaxing at home. To my delight, there were also three swimming pools in the complex. One of the pools were in the middle of the community which was right down the street from our home, then there were two others inside the clubhouse which were also fantastic. We really enjoyed the hot tub and sitting underneath the shelter when it started to rain. Since I knew it would be very hot and we would be extremely exhausted, I asked for a maid service halfway through our vacation and I'm so happy I did. It was nice to come home after dinner to a 100% clean house with clean towels and everything perfect. I recommend that you get the service as the cleaning lady does an excellent job! The next time we booked our Walt Disney World vacation I will be using this home again without a doubt. Even though we stayed 7 days, we still did not get to see everything that we wanted to. Next time we come down we are doing 10 to 12 days for sure and cannot wait to come back to Vista Del Lago. I was really surprised on how many friends we made while we were there!! If you are looking for a family home that could easily sleep 7 people, please do yourself a favor and book this, you will be so glad that you did!!

Responds fast! avg. 1 hour 20 minutes

5 of 6 match: Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$189

Completely Remodeled Coastal Condo

Saint Simons Island townhouse

2 bedrooms / 2 bathrooms / sleeps 4

“nice place” The Condo was very nice & very clean, we enjoyed our stay and the owner was very nice and also gave us details on good places to eat and things to see. St Simon Island was beautiful. The only thing was we thought we could fish on the place but was told we could not by another owner.The owner did give us a place on a pier just 1/2 mild from were we stayed to fish and it was beautiful. It would have been a little more convenient if there had be a TV up stairs since we did not care to watch most of the things our husbands watch, but other than these two things it was great.

Responds fast! avg. 39 minutes

4 of 6 match: Shared outdoor pool (heated), Games room, Fishing, Ceiling Fans, Climbing frame, Private fishing lake or river

4 of 6 filters match

Price per night from

$143

The Ever After Estate - 12BR Sleeps 45 People & Has 62 Private Acres

Clermont house

11 bedrooms / 10 bathrooms / sleeps 46

“Everything you could ever imagine !!!” My new Wife and I just got back from our stay. We held our Wedding there. We had both our immediate families stay with us during 3 days of our 4 day stay. Plenty of room for all, we had 15 adults and 8 kids total. This place is just so amazing. My wife and I toured it prior to our stay and missed so many things because there is so much detail. Our favorite place was the pool area. The day after our wedding some of us hung out at the pool for a couple of hours. The kids all had a blast between the pool slide, video games, ball pit, mini golf, and movie room. This made it easy for us to focus on set up and tear down for the wedding. We had 220 guest during our day and everyone loved the place. Biggest question was how did you find this place. Great photos from our day hit facebook immediately with babies on the Carousels,kids playing mini golf, and people around the tropical pool setting. Andrew, Felicia, and his staff were very helpful. Andrew answered all our questions with fast response times through out the planning. Felicia was there when we checked in and ensured we were settled and answered any last minute questions. The detail andrew put into his Estate is amazing. Every thing out there takes you away from your everyday. We are so lucky that such an awesome place was shared with our family and friends to enjoy. It was the perfect place to hold our special day. The last day I spent an hour taking photos of the Estate in which I noticed the incredible landscape,a touch that just simply takes your breath away on the beauty of life. Andrew thought of it all. The only down fall, which was our fault, is that we did not have enough time to enjoy everything. This was due to a short stay, wedding set up and tear down. Our next stay will be longer. My older Sister from Philly was talking about a family meet up next year. Boy I Hope so. All our Wedding dreams came true. Thank you Ever after Estate and Thank you andrew.

Responds fast! avg. 2 hours 36 minutes

5 of 6 match: Shared outdoor pool (heated), Fishing, Ceiling Fans, Climbing frame, Games room, Private fishing lake or river

5 of 6 filters match

Price per night from

$1,985

2 BDRM~ HISTORIC POWHATAN~INDOOR & OUTDOOR POOLS/HOT TUBS/ NEAR BUSCH GARDENS

Williamsburg condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 56 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$147

2 to 4 Jan Orlando 3 bedroom Disney Golf 7 Pools everything you need

Kissimmee condo

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 2 hours 49 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$188

2 BDRM~ HISTORIC POWHATAN RESORT~ HEATED INDOOR/OUTDOOR POOLS/GREAT LOCATION

Williamsburg condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 56 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$147

Busch Gardens-Convention Ctr- Downtown-River Cotta

Tampa cottage

1 bedroom / 1 bathroom / sleeps 4

“First time experience” I was very hesitant when my friend suggested renting a town home. We were in Tampa for the It Works convention and I had never done this before. I must admit it was a good first experience and even though we did not take advantage og the amenities it was good to know they were available. I will do this again!

Responds fast! avg. 3 hours 25 minutes

4 of 6 match: Shared outdoor pool (heated), Games room, Fishing, Ceiling Fans, Climbing frame, Private fishing lake or river

4 of 6 filters match

Price per night from

$132

Gated Resort, 6 BR, 5.5 BA, 4 Masters, South-facing Pool/SPA/Lanai/GameRm/Wifi

Orlando villa

6 bedrooms / 6 bathrooms / sleeps 15

Responds fast! avg. 1 hour 24 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$182

Orlando condo at Legacy Dunes - resort amenities

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 49 minutes

5 of 6 match: Private fishing lake or river, Fishing, Ceiling Fans, Climbing frame, Shared outdoor pool (heated), Games room

5 of 6 filters match

Price per night from

$86

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