Smoking friendly vacation rentals in Osceola County

4.81 out of 5 average rating, 214 reviews

10 mins to Disney! Beautiful 3/2 Kissimmee Condo

Located in a gated community, this home is only 10 minutes away from Disney Enjoy newly updated laminate flooring in this spacious 3 bed getaway for you and your loved ones. Tons of places to eat within walking distance! There's also entertainment such as mini-golf, smaller water parks etc. Enjoy the safety of a gated neighborhood. Once you're inside your home feel free to use the Roku device. You can log-in to your Netflix, Hulu, or simply use YouTube or one of the Roku channels for free :)

4.94 out of 5 average rating, 177 reviews

Guest suite in Kissimmee

Temple & glamping w/ spa tub under a 120 y/o tree

How this Airbnb was born? Me and my husband wanted to create a space to enhanced our soul, power our mind, fuel ourselves, to meditate, to create ideas, to be a part from the world, The Temple. Glamorous Camping idea came across, oh my!, once you go inside this tent, you don't want to come out. Friends and family started asking, can I stayed?, day by day closer people want it to live this experience and more positive comments we were getting, so we decided, why don't let others try it? Welcome.

4.95 out of 5 average rating, 77 reviews

Waterfront next to Resort by Disney Game &Theater

Lakefront Luxury Everything is Completely remodeled 5 bdrms\5 bthrms luxury villa – Located in the gated Paradise Palms Resort,which is just around the corner from Disney. Only a few steps away from the Clubhouse amenities & nature path,this home offers privacy & lake\nature views from the sun soaked south facing color changing pool\spa.Enjoy , New home theater, two 1st floor master bdrms & 2 bthrms + another master & immersive themed rooms on 2nd floor. AC Arcade TV gameroom & billiards Loft

4.88 out of 5 average rating, 90 reviews

Townhouse in Kissimmee

No Airbnb Fee | 2 King Suites | Near Disney

Welcome to this newly updated spacious townhouse located in a quiet, gated resort. Large enough to accommodate up to 10 people, this home has everything you need. While this beautiful home is perfect for a private getaway for you and the family, its location makes it easy for you to get around. You are only: 8 Minutes to Disney World 10 Minutes to Sea World 15 Minutes to Universal Studios 5 Minutes to Old Town 5 Minutes to Shopping and Restaurants 25 Minutes to Orlando International Airport

4.98 out of 5 average rating, 90 reviews

Home in Lake Wales

Lakefront Views! Private Dock! Great Bass Fishing!

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

4.93 out of 5 average rating, 90 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

5 out of 5 average rating, 13 reviews

Home in St. Cloud

Pool+Fire Pit+Grill+by Lake & Disney|Disco themed

Enjoy a freshly brewed cup from our coffee/tea bar. Ninja drip coffee machine, with creamer and sugar. Dip into our stock tank pool. Cozy up by the fire pit for stargazing. Cook delightful meals on the grill in a private yard. Fun and colorful decor. Custom selfie wall. 70” smart TV to stream your favorite shows. Shampoo, conditioner, body wash, towels provided. Bedside lamps & outlets for convenient phone charging in every room. High chair & Pack n Play behind the sofa

4.95 out of 5 average rating, 80 reviews

Spacious Disney Retreat - Sleeps 7 - Pet Friendly

Enjoy a stay where laughter fills the air and every family member is catered for. Our guest-favorite, dog-friendly retreat, perfectly located just minutes from Disney. This home-away-from-home is designed to accommodate a family of 7, offering cozy comfort, ultimate convenience, and memorable experiences for all. Self-check-in, FAST WiFi, and a fully-equipped kitchen, you can relax and enjoy your stay without worry in the world. Book early, our calendar fills quickly!

5 out of 5 average rating, 38 reviews

Family Vacay with Pool near WDW!

We hope to welcome you to this enchanting family retreat in Kissimmee, Florida, just 20 minutes from the magic of Walt Disney World Resort! This sunlit oasis is designed for unforgettable family vacations. Dive into your screened private pool, a cool oasis under the warm Florida sun, to create memories that'll last a lifetime. After an exhilarating day at the parks, return to this cozy home where you'll find the perfect blend of entertainment and relaxation.

4.86 out of 5 average rating, 643 reviews

Guest suite in Kissimmee

Private Studio in POOL home

Hello travelers! 😀 We offer a portion of our smoke-free home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the area with access to Roku. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio to travelers.

Superhost

Guest suite in Kissimmee

4.83 out of 5 average rating, 588 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers! 😀We offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We offer our home to travelers only-we do not accept local reservations.

4.93 out of 5 average rating, 55 reviews

Family Getaway w/ Pool & Arcade – Near All Parks !

Discover Your Perfect Getaway in Kissimmee! Whether you seek a tranquil retreat or an adventurous vacation, this house has it all. Enjoy the pool on hot Florida days and relax in spacious comfort. Just 17 minutes from Orlando Airport (MCO) and close to all major attractions: Disney World, SeaWorld, Universal Studios, and an hour from Cocoa and Daytona Beach. Book now for an unforgettable stay!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Osceola County smoking friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Smoking friendly apartment rentals

3.75 out of 5 average rating, 4 reviews

Clean, Cozy Space with Resort Amenities

EderRating, 5 stars1 month ago

I had a very nice days out there. Everything since the check-in was perfect. I felt like I was at my own house. Clean, organized, quiet, very nice location - closed to parks, restaurants and grocery markets. I’ll certainly be back.

4.75 out of 5 average rating, 4 reviews

Cue the Sunshine – The Irlo Studio Getaway

HamiltonRating, 5 stars1 month ago

This Airbnb is perfect for couples and it’s a great price and great location

4.97 out of 5 average rating, 71 reviews

Apartment in Polk County

Shady Lawn Lodge

DaisyRating, 5 stars1 week ago

Ronnie place was amazing, hot tub was incredible, spotless everything was clean! He also offered us to stay later than our check out time! Book with him no regrets!

SeandraRating, 5 stars1 month ago

Grand Family 3BR Apartment near Disney Parks #10

Enjoyed the place very nice

5 out of 5 average rating, 11 reviews

Themed Luxury Apartment With Pools/Jacuzzi

RicoRating, 5 stars3 months ago

We loved the stay, especially the kids. Lots to do in the area, was definitely a great weekend.

4.67 out of 5 average rating, 3 reviews

3bed/2 bath European style.Free Resort.Disney 8min

MeagRating, 5 stars11 months ago

great planes especially if you are visiting disney

ManuelRating, 5 stars3 months ago

2778 Windsor Hills 3 Bed Condo- All Included

Very nice stay. The apartment is impeccable, the responsible always helpful.

DominicRating, 5 stars50 months ago

A place to be for your vacation

Don’t hesitate to book with Zora! We stayed with her multiple times and each time the communication has been excellent. We appreciate her transparency with the amenities that came with our stay. Each time that we’ve stayed with her, we have benefited from owner’s perks such as access to Shipwreck Island and 20% of restaurants. We can’t wait to book with Zora again soon!

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Smoking friendly house rentals

5 out of 5 average rating, 3 reviews

9Br/6Ba Pool Villa,Near Disney

Barbara AnnRating, 5 stars3 months ago

We stayed for almost the entire month of February and didn't want to leave. The size was perfect for our large extended family and the additional upstairs living room was great to have for our super bowl party! The home and pool area were so beautiful and peaceful. The amenities, complete with water park and lazy river, were absolutely amazing; we felt like we were living in a resort! Our host was very quick to respond when I reached out with questions. This house has everything everyone could want or need for any length stay. Highly recommended!! Thank you, Iverson!

4.88 out of 5 average rating, 8 reviews

Home in Haines City

Paraiso Soleado

AriaRating, 5 stars1 month ago

Loved the home Beautiful and very clean

4.64 out of 5 average rating, 76 reviews

Mickey & Coco-Themed Rooms! Pool| BBQ| Mini Golf

DianeRating, 5 stars3 months ago

It was a very beautiful home comfortable… And the host responded very quickly to all my questions I had… I for share will visit again

5 out of 5 average rating, 4 reviews

Peaceful Caribbean

RobertoRating, 5 stars1 week ago

The house was great, we would definitely visit it again. My family loved it, we'll be back soon! Thank you so much!

4.61 out of 5 average rating, 36 reviews

Luxurious Townhome in Storey Lake

NickRating, 5 stars26 months ago

Perfect proximity to the community center, quick and easy access to shops and restaurants. Only 20 to 25 minutes to Disney and Universal. (Disney is far better.) Everyone in my group was impressed with the place and loved the private pool. The place is big enough that any noise in the living room / kitchen isn't heard in the bedrooms upstairs. The place looks a little more posh than the photo's give it credit for. My wife wanted to bookmark this place over any future stay at a Disney resort. Tips for your stay, not a negative though: Beds are firm. Wait like... 4 to 5 minutes for the hot water to kick in at the showers.

Home in Davenport

4.7 out of 5 average rating, 23 reviews

Beautiful Home Away from Home

LyndseyRating, 5 stars2 months ago

Nancy was awesome and very responsive house was beautiful and very clean kids enjoyed the big pool and their is two seating areas near pool which I really liked it also is close to everything we look forward to staying again🤗

4.72 out of 5 average rating, 29 reviews

Summer in Storey lake / 16 people

KamilleRating, 5 stars1 month ago

Stayed her for 5 days on a Family vacation with 10 guests. The house was so amazing , looks exactly like the photos, very spacious , nice area, we barely left the house , everything we needed was already there. We spent most of our days in the pool and cooking on the grill. Lisbeth made sure our stay was perfect. She was always available if I had a question and check in was easy. Absolutely loved this property . I will be back.

4.89 out of 5 average rating, 54 reviews

Amazing home near airport and major parks - WIFI

AmyRating, 5 stars14 months ago

Anthony’s place was perfect for our stay in Kissimmee. The house is lovely and had lots of supplies that made our stay easy and enjoyable. Would definitely stay here again!

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Smoking friendly condo rentals

Condo in Orlando

5 out of 5 average rating, 4 reviews

Total Bliss (luxury condominium)

JerryRating, 5 stars50 months ago

This is the perfect location. Near restaurants, near activities. The home was beautifully decorated the Pool was heated and it had everything we needed to cook and enjoy.

4.67 out of 5 average rating, 9 reviews

Luxury mini-suite by the WORLDS BEST THEME PARKS

BethRating, 5 stars47 months ago

Perfect spot if you want to be in the middle of everything 10 minutes from Magic Kingdom. Very clean. Great staff. Would definitely recommend!

4.93 out of 5 average rating, 15 reviews

Orange Lake Resort -Heart of family fun

KevinRating, 5 stars1 month ago

We have stayed at Orange Lake multiple times and have always enjoyed it. This was nothing different. Vacation was very easy to deal with and would recommend booking anytime with them.

Superhost

KellyRating, 5 stars41 months ago

Orlando Fantasy World

Great host- excellent communication and property as described.

AnneRating, 5 stars29 months ago

Rent Luxury and confortable apartments.

Nice place. Well worth it.

LydiaRating, 5 stars41 months ago

Kissimmee Resort - Entire Condo/Suite

Had a hiccup with the dates but Sarah made it right and it was a wonderful stay.

4.83 out of 5 average rating, 6 reviews

Close to the best Disney theme parks

LaikynRating, 5 stars5 months ago

First off, I just want to say this was a great place! I would love to come back in the future and stay at this property. Carlos was a great host and responded very quickly if we needed something. I absolutely loved how there were so many things to do on property.