Kissimmee Listings

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Monthly Rent $2630.00 - $4500.00

3BR | Patio | Pool | Dog Friendly Kissimmee, Florida, Listing ID: 32727

When you visit Central Florida, you want the best of both worlds: non-stop fun and excitement at the theme parks during the day, and non-stop relaxation and recharging at night. And that's exactly what you'll get at this beautifully updated, family- and dog-friendly condo. Three...

  • Apartment
  • 1357
  •  3
  •  2
Monthly Rent $2910.00 - $6670.00

3BR Dog Friendly | Private Pool | Hot Tub | Patio Kissimmee, Florida, Listing ID: 32728

This stylish and eclectic townhome is full of fun Disney decor, perfect to get your friends and family excited about visiting Disney World! Experience this exciting resort and feel your cares melt away as you make memories with your loved ones. Not only do you have your own...

  • Townhouse
  • 1295
  •  3
  •  3
Monthly Rent $2800.00 - $3430.00

3BR dog-friendly stay with resort amenities Kissimmee, Florida, Listing ID: 32731

Experience the getaway of a lifetime at this charming and bright retreat in Kissimmee! This condo is perfect for those looking for the ideal home base to explore and experience Disney and all of its entertainment. Two comfortable couches are conveniently placed near a flatscreen...

  • House
  • 1275
  •  3
  •  2
Monthly Rent $2180.00 - $3960.00

2BR | Balcony | Pool | Dog Friendly Kissimmee, Florida, Listing ID: 32732

Tell the whole family (including the pups) that they're going to Walt Disney World and reserve this charming condo with a furnished balcony, updated kitchen, and space for up to six guests. Everyone will also enjoy a number of on-site resort amenities including a shared swimming...

  • Condo
  • 1015
  •  2
  •  2
Monthly Rent $2800.00 - $4310.00

3BR townhome with pool, hot tub, foosball Kissimmee, Florida, Listing ID: 32733

Welcome to your Florida home away from home and your perfect hideaway while you experience Walt Disney World and Universal Studios just down the road! With access to a small community pool and hot tub, leisure and relaxation are at your fingertips. Kids will loved the...

  • Townhouse
  • 1862
  •  3
  •  3
Monthly Rent $2950.00 - $5220.00

3BR Gulffront | Patio | Pool | Dog Friendly Kissimmee, Florida, Listing ID: 32734

Looking for quick access to theme parks and tons of amenities at home? Look no further than this three-bedroom condo in the Reunion Resort, an award-winning community with seven swimming pools, a spa and wellness center, a rooftop bar and restaurant, a hot tub, and much more....

  • Condo
  • 1757
  •  3
  •  3
Monthly Rent $2910.00 - $4300.00

Dog Friendly 3BR | Pool | Laundry | Central AC Kissimmee, Florida, Listing ID: 32729

Enjoy your stay at this tranquil family home, set on the shores of a neighborhood lake! Relax inside central air conditioning and cook together in a spacious full kitchen (with plenty of counter space for all your dishes). A ceiling fan and TV in each room allow every guest to...

  • House
  • 1798
  •  3
  •  3
Monthly Rent $2100.00 - $3960.00

2BR dog-friendly condo with pools, W/D, fast WiFi Kissimmee, Florida, Listing ID: 32726

Conveniently located 10 miles away from Disney World, this marvelous and well-equipped condo is a must-see! Enjoy a prime location within the Tuscana Resort Orlando, featuring fantastic on-site amenities that include an outdoor pool, a children's pool, and a fitness center. A...

  • Condo
  • 1134
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $2500.00

Budget Friendly 3 BR Disney Area Kissimmee, Florida, Listing ID: 31681

Enjoy all the comforts of this amazing 3 bedroom condo that accommodates comfortably up to 6 people! This spacious home comes with a spacious living/dining area and a fully equipped kitchen. This is definitely the best option to create the story of a perfect vacation with...

  • Home
  • 1287
  •  3
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $3500.00

Come & Enjoy a beautiful, bright apartment with lake view from private balcony & many amenities Kissimmee, Florida, Listing ID: 29554

Your perfect Florida/Disney getaway starts here. Lovely condo fully furnished & equipped, ready for you and your family. An upstairs unit with private patio & spectacular water views of frequent visits  cranes, turtles and other fauna. Amenities including a beautiful clubhouse...

  • Apartment
  • 1220
  •  3
  •  2

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Monthly Rent $1990.00 - $4690.00

2BR bayfront with pool, hot tub, gym, & balcony St. Pete Beach, Florida, Listing ID: 33014

This Holiday Island condo is the perfect choice for a Gulf Coast getaway. Boasting beautiful views of Tampa Bay, this first-floor waterfront condo comes complete with on-site access to a fabulous suite of amenities and offers an unbeatable location near the beach and St....

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2BR Waterview Dog Friendly | Private Pool | Dock St. Petersburg, Florida, Listing ID: 33017

Classic Florida charm meets modern coastal style at this stunning and very private 2BR/2BA home, perfectly nestled in a beautiful Intracoastal cove with stunning views. Tropical landscaping, cool ocean-inspired tones, chic beach decor, and an abundance of natural light fill the...

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Monthly Rent $5920.00 - $20880.00

Chic 3BR Oceanview Dog Friendly | Pool | Deck St. Petersburg, Florida, Listing ID: 33018

Modern Intracoastal retreat meets alluring outdoor living best describes this beautifully remodeled 3BR/2BA home. Located on a quiet cul-de-sac, this stunning oasis overlooks 150' of seawall with spectacular views. Take a dip in the waterfront pool while burgers sizzle in the...

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Monthly Rent $2402.00 - $4906.00

Monthly DOG-FRIENDLY St. Pete, 2BR (Sleeps 4) 1BA downtown district w/covered porch, fenced patio Rent: $2,402 - $4,906 St. Petersburg, Florida, Listing ID: 33019

St. Pete Birds Nest - St. Petersburg, FL Dog-Friendly Second-Floor Retreat with WiFi, Private Patio, & Great Location You can’t get cuter than this second-floor, two bedroom retreat, right in the heart of St. Pete. You’re just two blocks north of Central Avenue...

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  •  1
Monthly Rent $1990.00 - $4620.00

2BR Dog Friendly | Patio | W/D | Snowbird Friendly St. Petersburg, Florida, Listing ID: 33020

Your own private party begins now: with a backyard tiki bar, gas grill, and large patio, you'll have to force yourself to leave and explore the city around this cute St. Pete hideaway. Inside, you'll find a one-level layout, decorated in a sweet Florida style. The bright and...

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  • 1032
  •  2
  •  1
Monthly Rent $2477.00 - $7360.00

2BR Dog Friendly | Hot Tub | Patio | Firepit St. Petersburg, Florida, Listing ID: 33021

Colorful quarters, sparkling waters, and magical amusements can be found every day at your stay in Petersburg. Nearby, curate fun memories at the St. Petersburg Saturday Morning Market, Sunken Gardens, and Smugglers Cove Adventure Golf. Pulling up to your stay, quickly fall for...

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  • 1218
  •  2
  •  2
Monthly Rent $3500.00 - $3880.00

Dog-friendly home with enclosed lanai, & washer/dryer Port Charlotte, Florida, Listing ID: 33158

A charming, updated home tucked into a residential neighborhood, this sunny, one-level space positions you just minutes from golf courses, the beach, shopping, restaurants, and other amenities. Spend days with your toes in the sand at Port Charlotte Beach Park, around four miles...

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  • 1028
  •  2
  •  2
Monthly Rent $3000.00

$3,000, Beach Community, 55+ Newly Renovated Corner Villa 2BR/2BA garage, Club House, pool, spa, RV, <25 lbs pet/dog Hobe Sound, Florida, Listing ID: 33187

Experience the best of Florida’s scenic beauty in this tranquil 55 + beach community of Hobe Sound. Beautifully Renovated Fully Furnished, 2 Bedroom 2 Bathroom, One-story Corner Villa with Garage, Extra Air-conditioned Sunroom, and high-end finishes. Flexible leasing minimum...

  • Villa
  • 1306
  •  2
  •  2
Monthly Rent $2910.00 - $4650.00

3BR 2nd-Floor | Balcony | Dog Friendly | W/D Orlando, Florida, Listing ID: 33280

All the magic of Orlando is right at your doorstep in this comfortable, second-floor condo located in the Worldquest Resort. Start your day on your covered balcony, cup of coffee in hand. Take your time – you’re on vacation. When you start getting hungry, head inside to your...

  • Condo
  • 1421
  •  3
  •  2
Monthly Rent $3080.00 - $4400.00

Large 3BR Lakefront Dog Friendly | Patio Tampa, Florida, Listing ID: 33282

This charming, lakefront home is well-prepared to host your next getaway! Located in vibrant Tampa, the opportunities for fun are truly endless. During your stay, take a walk over to the University Area Community Park and the Gregory Drive Butterfly Garden. Practice your game at...

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  • 1412
  •  3
  •  2
Monthly Rent $2500.00 - $4170.00

3BR Dog Friendly | Tennis | W/D Tampa, Florida, Listing ID: 33283

This darling home sits on a grassy piece of property in the Oakford Park neighborhood of Tampa. It is full of color, style, and just the right amount of whimsy. Enjoy a shaded front porch and a spacious backyard, great for families and furry companions, as well as community...

  • House
  • 910
  •  3
  •  1
Monthly Rent $3720.00 - $6810.00

Dog Friendly 3BR | Private Pool | Screened Porch Tampa, Florida, Listing ID: 33284

Laid-back Florida living awaits you at this gorgeous Tampa home. Within steps Bonnie Brae Park, this three-bedroom retreat comes complete for modern comfort, with highlights including a fully fenced yard and sparkling, in-ground pool. The surrounding patio is furnished for...

  • House
  • 1821
  •  3
  •  2
Monthly Rent $4453.00 - $6490.00

Dog Friendly 3BR | Kayaks | SUP | Walk to Beach Venice, Florida, Listing ID: 33285

Nestled in the shade of mature trees just two blocks from the Gulf of Mexico, this three-bedroom Venice home is so close to the beach, you can greet each morning with a sunrise swim. This single-level home was designed to make the most of the beautiful Florida weather. There are...

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  • 1749
  •  3
  •  3
Monthly Rent $5970.00 - $7210.00

4BR DOG FRIENDLY | Patio | Firepit | W/D Bradenton, Florida, Listing ID: 33332

Villa Tessa - dog-friendly, jetted tub, firepit, beaches, Ana Maria Island, IMG

Welcome to Villa Tessa! You are right in the middle of the action, close to beaches, downtown Bradenton, Sarasota, Tampa, Clearwater, St. Petersburg, and more.

This large,...

  • House
  • 2204
  •  4
  •  3
Monthly Rent $3039.00 - $6892.00

Oceanfront 2BR | Pool | Gulf View | Steps to Beach Holmes Beach, Florida, Listing ID: 33334

Ocean-front condo with WiFi, pool & Gulf views - steps to the beach

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

Treat yourself to a magical Florida...

  • Condo
  • 1000
  •  2
  •  2
Monthly Rent $2789.00 - $7236.00

Prime 2BR Gulffront | Balcony | Pool Holmes Beach, Florida, Listing ID: 33335

Seaside family-friendly condo with WiFi, pool & prime location

*Please note that this home only allows minimum night stays of 30 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

Come enjoy this family-friendly condo that...

  • Condo
  • 1280
  •  2
  •  2
Monthly Rent $2250.00 - $3620.00

DOG FRIENDLY Cinnamon Shores Hideaway - Ormond-By-The-Sea, FL Ormond-By-The-Sea, Florida, Listing ID: 33337

Oceanfront condo with great views, steps to Cinnamon Sand Beach

*Please note that this home only allows minimum night stays of 29 nights or longer. This is enforced by the HOA and we cannot make any exceptions.

This cozy oceanfront condo is only steps...

  • Condo
  • 780
  •  1
  •  1
Monthly Rent $3291.00 - $5806.00

Stunning 2BR Oceanfront | Balcony | Pool Longboat Key, Florida, Listing ID: 33339

Oceanfront townhouse w/ shared pool and stunning panoramic water views

Located at the north end of Longboat Key, this spacious townhome offers everything you're looking for in a vacation home! With stunning Gulf views from the living room and the master bedroom,...

  • Condo
  • 1350
  •  2
  •  3
Monthly Rent $4900.00 - $5453.00

3BR with deck, garage parking, & W/D St. Augustine, Florida, Listing ID: 33340

Inviting beach house - walk to beach, shopping & dining

This open layout beach house is made for making memories and relaxing beach getaways! Boasting a private enclosed backyard for fresh-air fun, a large flatscreen TV with free WiFi back inside, this home has...

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  • 1102
  •  3
  •  2
Monthly Rent $12000.00 - $15989.00

2BR dog-friendly with pool & balcony Anna Maria, Florida, Listing ID: 33341

Dog-friendly home with heated private pool & short walk to the beach

This lovely beach home is freshly decorated with coastal decor. This home comes equipped with a private heated pool, a grand poolside lounge, and a spacious outside dining area for barbecues....

  • House
  • null
  •  2
  •  3
Monthly Rent $2578.00 - $6412.00

Renovated 1BR Oceanfront | Deck | Pool Longboat Key, Florida, Listing ID: 33343

Beachfront Condo with a Beautiful, Renovated Kitchen, Shared Pool, & Tennis

Life is good at Whitney Beach! From the moment you enter the private courtyard patio, you'll realize you've finally found the island retreat you've been looking for. This inviting,...

  • Condo
  • 1084
  •  1
  •  2
Monthly Rent $8250.00 - $17767.00

Beautiful 3BR Gulfview | Pool | Patio Longboat Key, Florida, Listing ID: 33344

Beautiful home boasting private pool & private beach access

This beautiful and spacious family-friendly home is perfect for your next beach getaway. Only 250 feet from your door, you will find the private beach access point leading you to the azure waters of...

  • House
  • 1937
  •  3
  •  3
Monthly Rent $2302.00 - $6013.00

Gulf-front 2BR condo with beach access Treasure Island, Florida, Listing ID: 33345

Gulf-front condo near golf with beach access & heated pool - snowbird-friendly

With views of the gulf and the intercostal, this beachy condo boasts relaxation in a prime beachfront location. Enjoy spectacular Florida sunsets over the gulf from the private...

  • Condo
  • null
  •  2
  •  2
Monthly Rent $2777.00 - $5739.00

Corner Condo 3BR Oceanfront 3rd-Floor | Balcony Madeira Beach, Florida, Listing ID: 33362

3rd-floor oceanfront corner condo with on-site pool & ocean views

Enjoy a stellar ocean view from your wide furnished deck - yes, the beach really is that close! This luxurious corner condo features wood-style flooring and central air conditioning for maximum...

  • Condo
  • 1265
  •  3
  •  2
Monthly Rent $1984.00 - $3292.00

Walk to Downtown 2BR Dog Friendly | Patio | W/D St. Petersburg, Florida, Listing ID: 33366

Golden Getaway | Historic District Charmer | 15-Minute Walk to Downtown

Brought to you by the family of Rue McClanahan -- your favorite Golden Girl -- this charming 2BR home is inspired by the popular 80s sitcom. Nestled in a historic district with brick roads...

  • Duplex
  • null
  •  2
  •  1
Monthly Rent $3242.00 - $8277.00

Waterfront 3BR | Private Pool | Dog Friendly St. Petersburg, Florida, Listing ID: 33370

Harbor Isle Waterfront Retreat | Home Office & Private Pool | Kayaks & Canoe

Perfect for canoeing and kayaking, this 2,780 square foot 4BR/2.5BA waterfront retreat is located in the desirable Harbor Isle neighborhood. You're also situated directly across an...

  • House
  • null
  •  3
  •  3
Monthly Rent $3600.00 - $5618.00

Dog friendly 3BR | Patio | Yard | W/D | Central AC Clearwater, Florida, Listing ID: 33382

DOG FRIENDLY (Up to 4 dogs!) getaway with enclosed yard, central AC, & W/D - Snowbirds Welcome!!

Experience the Sunshine State at this ground-floor home away from home and treat your family to an unforgettable escape! This home is ideal for families with kids,...

  • House
  • 936
  •  3
  •  2
Monthly Rent $2990.00 - $5083.00

3BR Golf Course View Dog Friendly | Private Pool Flagler Beach, Florida, Listing ID: 33384

DOG FRIENDLY (Up to 4 Dogs) Home near the Beach w/ Private Outdoor Pool, Central AC, Free WiFi

There's no vacation like a truly relaxing getaway to the beach and Ocean Palm Getaway is your prime choice! This darling home has been recently updated with all new...

  • House
  • 1986
  •  3
  •  2
Monthly Rent $3852.00 - $6199.00

3BR Oceanview | Dock | Balcony | Tennis | W/D New Smyrna Beach, Florida, Listing ID: 33387

Snowbird-Friendly, Ocean View Home with Fast WiFi, Central AC, & Washer/Dryer

Three levels means three levels of balconies with ocean and Intracoastal views! Beautifully furnished from stem to stern, this family-friendly beach home features all the amenities...

  • House
  • 2500
  •  3
  •  5
Monthly Rent $3640.00 - $4054.00

2BR Soundview Bungalow | Patio | W/D St. Petersburg, Florida, Listing ID: 33389

Located in a quiet neighborhood in historic Old Northeast, this charming 2BR/2BA mid-century bungalow promises a unique stay. Walk to Coffee Pot Park and launch the provided kayaks onto the bayou for a thrilling day on the water. (If visiting during winter, keep your eyes peeled...

  • House
  • 1224
  •  2
  •  2
Monthly Rent $4500.00 - $10230.00

3BR Golf Course View | Patio | Golf | W/D Bradenton, Florida, Listing ID: 33395

Screened Golf-Front Back Patio w/Grill, and Florida Room w/Wet Bar & Wine Fridge, Free Parking

Overlooking beautifully landscaped grounds with a walking path and the lush greens of Tara Golf & Country Club just beyond, this home offers a pristine...

  • House
  • 1994
  •  3
  •  2
Monthly Rent $1628.00 - $5235.00

Convenient 1BR | Dog Friendly | Walk to Sand Cape Canaveral, Florida, Listing ID: 33396

Convenient, dog-friendly beachside condo with AC & beach chairs - walk to sand

Set sail for an (inter)stellar stay at this Space Coast condo. Just steps from the beach, local dining options, and attractions, this breezy retreat is primed for laid-back seaside...

  • Condo
  • 506
  •  1
  •  1
Monthly Rent $5370.00 - $7116.00

Comfortable 3BR | Pool | Patio | Snowbird-friendly Bradenton, Florida, Listing ID: 33397

Great location with Screened Pool & Hot Tub/Spa Lanai and Grill near Mall and Golf

Take a break from the hustle and bustle of everyday life and spend some quality time with friends and family. Soaking up sweet sunshine will be a breeze with the wonderful...

  • House
  • 2174
  •  3
  •  2
Monthly Rent $4296.00 - $19278.00

Luxe 3BR Oceanfront | Balcony | Pool Clearwater Beach, Florida, Listing ID: 33399

Luxe beach-view condo next to Pier 60 - pool, hot tub, gym & grilling area

Step away from your daily routine, the ordinary, and step into the extraordinary at this gem of a condo. Pamper yourself in the luxuriant Mandalay Beach Club on San Marco, which boasts...

  • Condo
  • 1600
  •  3
  •  2
Monthly Rent $3239.00 - $9148.00

Ocean Views from Living Room, Balcony and Pool! Modern beachfront condo with WiFi, Free Parking, Snowbirds Welcome Redington Beach, Florida, Listing ID: 33400

Redington Place 301: Ocean Views from Living Room, Balcony and Pool! Modern beachfront condo with WiFi, Free Parking, Snowbirds Welcome

*30 day minimum stay required or calendar month. Please note that this property requires paperwork to be completed 7 days...

  • Condo
  • 1310
  •  2
  •  2
Monthly Rent $3678.00 - $10077.00

Beachfront 2BR | Pool | Balcony | AC | W/D Redington Beach, Florida, Listing ID: 33401

Redington Place 201: Ocean Views from Living Room, Balcony and Pool! Modern beachfront condo with WiFi, Free Parking, Snowbirds Welcome

*30 day minimum stay required or calendar month. Please note that this property requires paperwork to be completed 7 days...

  • Condo
  • 1310
  •  2
  •  2
Monthly Rent $6000.00 - $12786.00

2/2.5 w/patio, views of the Intracoastal and backyard marina, w/Seaside Heated Pool, Hot Tub, Sauna, Fitness Center Clearwater, Florida, Listing ID: 33402

Spacious w/patio, views of the Intracoastal and backyard marina, on Mandalay Channel, with Seaside Heated Pool, Hot Tub, Sauna, Fitness Center and 2-story Clubhouse

*Complex restrictions apply. Only one guest per month and paperwork required 30 days prior to...

  • Condo
  • 1619
  •  2
  •  3
Monthly Rent $2160.00 - $4061.00

Ground floor condo in Gated Community with Pool and Tennis, fast WiFi, central full kitchen St. Petersburg, Florida, Listing ID: 33404

Ground floor condo in Gated Community with Pool and Tennis, fast WiFi, central full kitchen

Ground floor condo with fast WiFi, central AC, full kitchen, and washer/dryer Come inside and relax in a casual condo cooled by central air conditioning - the shared...

  • Condo
  • 1100
  •  2
  •  2
Monthly Rent $1748.00 - $4197.00

Ground-Floor Condo w/Covered Patio, Beachfront Community Ocean-view Pool New Smyrna Beach, Florida, Listing ID: 33405

Seaward D-101: Ground-Floor Condo w/Covered Patio, Beachfront Community Ocean-view Pool - WiFi, Snowbirds Welcome

Enjoy a prime beach location at this charming condo, just steps away from the sand on the no-drive section of New Smyrna Beach. As part of the...

  • Condo
  • 720
  •  1
  •  1
Monthly Rent $2503.00 - $7125.00

DOG FRIENDLY with Private Balcony overlooking the Water. Quiet condo with Pool, Lanai, Golf Rotonda West, Florida, Listing ID: 33406

DOG FRIENDLY with Private Balcony overlooking the Water. Quiet condo with Pool, Lanai, Golf.

Sunny rays, front-row seats to the cape, and lush greenery make up the gorgeous scenery at this condo in Rotonda West. Serene and quiet, this condo is conveniently...

  • Apartment
  • 1543
  •  2
  •  2