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Longwood Rentals

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From $184 per night (USD)
VRBO
Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Unwind in a comfortable and well-equipped home, conveniently located near Orlando/Sanford Airport, Wekiwa Springs, and a ...
From $184 per night (USD)
VRBO
From $428 per night (USD)
Expedia
Spacious and relaxing Home - North Of Orlando In Longwood, Florida
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
You’ll love our home because of the coziness, and beautiful garden view. Our house is good for couples, business travele ...
From $428 per night (USD)
Expedia
From $226 per night (USD)
VRBO
Peaceful Longwood Home - Minutes to Attractions
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Beautiful, cozy, and welcoming home in Longwood. Conveniently located near Historic Downtown Longwood, hospitals, shoppi ...
From $226 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Cozy & Charming Studio. Minutes from Disney & Epic Universe + Top Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Cozy and welcoming private studio with its own separate entrance for complete privacy. This charming space is decorated ...
From $161 per night (USD)
Expedia
From $331 per night (USD)
VRBO
Pool Access! Dog-Friendly Retreat 16 Mi to Orlando
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Immerse yourself in easy Florida living with this sun-drenched, single-level Longwood home boasting a perfect location a ...
From $331 per night (USD)
VRBO
From $170 per night (USD)
Expedia
The Longwood Escape • Modern Private Guesthouse Near Orlando
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Longwood Escape, a private guesthouse designed for comfort and convenience. Enjoy a cozy bedroom with a q ...
From $170 per night (USD)
Expedia
From $112 per night (USD)
VRBO
Cozy Home in Longwood Historic District
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Keep it simple at this peaceful and centrally-located place. Longwood Historic District - BRAND NEW 2 bed/1bath home. S ...
From $112 per night (USD)
VRBO
From $80 per night (USD)
VRBO
Cozy 1-bedroom apartment in Historic Longwood with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great opportunity to stay in the lovely downtown Longwood Historic District. Cozy 1 bed/1bath upstairs apartment. Steps ...
From $80 per night (USD)
VRBO
From $1776 per night (USD)
VRBO
The American Dream House – Lakefront Luxury with 2 Heated Pools & Hot Tub
Bedrooms:
5
Bathrooms:
6
Sleeps:
22
A stunning lakefront retreat perfect for families. Enjoy two heated pools and a relaxing hot tub—the front pool is ideal ...
From $1776 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Downtown Historic Longwood steps to City park & SunRail
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Brand New Property Built 2022 in Bustling downtown Longwood with lots of Activities steps away. 45 minutes to beaches ...
From $394 per night (USD)
Expedia
From $430 per night (USD)
VRBO
Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This beautiful secluded Chalet in walking distance to Downtown Longwood, sits on 2 wooded acres part of our 6 acres comp ...
From $430 per night (USD)
VRBO
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VRBO
Luxury 2 room near Disney
Bedrooms:
2
Bathrooms:
2
Sleeps:
1
Near Disney, restaurants, Walmart, Publix , 2 bed 2 bath family friendly, brand new house, near the Sanford internationa ...
Click For Pricing
VRBO
From $297 per night (USD)
VRBO
Lakefront Home Where You Can Retreat And Relax
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discounts offered when staying 1 month or more. Located within a short distance to all of the theme parks, golf, canoei ...
From $297 per night (USD)
VRBO
From $323 per night (USD)
Expedia
This Charming House with an outdoor pool, 3 bedrooms, 2 full baths.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is a 3-bedroom 2-bath home, bathroom in the main bedroom connects directly to the pool. Accommodates comfortably up ...
From $323 per night (USD)
Expedia
From $154 per night (USD)
VRBO
Lake Marion Apt w/ Canoe in Altamonte Springs!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Plan an unforgettable retreat to celebrate an anniversary or your loved one’s birthday and stay at this Altamonte Spring ...
From $154 per night (USD)
VRBO
From $223 per night (USD)
Expedia
A Home Where Eclectic Luxury Meets Affordability
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to The Altamonte House. This home is in a prime location standing between Orlando's major theme parks and beauti ...
From $223 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Private Outdoor Oasis w/ Pool: Home in Longwood!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Cookout Ready | Themed Bedrooms | 29 Mi to WDW | Day Trip to Cocoa Beach Paradise awaits when you retreat with family o ...
From $614 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Relaxing lake house with AC in quiet Casselberry
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a peaceful stay at this 2-bedroom house in Casselberry. Each bedroom features its own queen mattress and closet. O ...
From $204 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Lakefront Villa in Casselberry
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Lakefront Comfort Near Orlando Escape to a peaceful retreat tucked away in Casselberry! This cozy home offers relaxing l ...
From $401 per night (USD)
VRBO
From $133 per night (USD)
Expedia
Charming 1-bedroom house in Casselberry
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This guest studio has its own private entrance, kitchen, washer and dryer, bathroom, and all important appliances (TV, F ...
From $133 per night (USD)
Expedia
From $160 per night (USD)
VRBO
Modern 2BR Stay in Prime Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $160 per night (USD)
VRBO
From $148 per night (USD)
Expedia
Bright & Comfy 2BR Home Away
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $148 per night (USD)
Expedia
From $132 per night (USD)
VRBO
2BR with Resort-Style Amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $132 per night (USD)
VRBO
From $128 per night (USD)
Expedia
Upscale 1BR Apartment Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $128 per night (USD)
Expedia
From $134 per night (USD)
VRBO
1BR with Open-Concept Living
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $134 per night (USD)
VRBO
From $93 per night (USD)
Expedia
Modern 1BR with Premium Finishes
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
From $93 per night (USD)
Expedia
From $667 per night (USD)
VRBO
The Tiki Palm- Screened Pool, Mini Golf, Arcade & Creekside Fun
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to The Tiki Palm Your private tropical-inspired Central Florida escape blending retro coastal vibes with resor ...
From $667 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Family Pool Home Near Orlando Attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious family-friendly home in Casselberry, FL featuring 3 bedrooms, 2 bathrooms, a private pool, and a fun game room ...
From $349 per night (USD)
VRBO
From $203 per night (USD)
VRBO
Spacious Casselberry Home Near Attractions. Host capacity up to 10 people
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Welcome to your perfect Central Florida getaway! This beautifully updated home in Casselberry offers comfort, style, and ...
From $203 per night (USD)
VRBO
From $235 per night (USD)
Expedia
The Frogs Castle
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Make memories at this relaxing and spacious home where you can recharge and enjoy everything that Orlando and its surrou ...
From $235 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Longwood Getaway with Pool Table, BBQ Grill & Outdoor Space!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your home away from home in the heart of Longwood, a peaceful, family-friendly neighborhood just minutes from ...
From $352 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Lakefront House | Kayak | Fish | Grill
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
🏡 THE SPACE Welcome to your private lakefront retreat — a peaceful 3BR/2BA single-family home on the shores of a privat ...
From $291 per night (USD)
Expedia
From $173 per night (USD)
VRBO
North Orlando Family Home
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Home in quiet family neighborhood, 3 bedrooms plus a loft/office, 3 bathrooms. Downstairs is the master bedroom and bath ...
From $173 per night (USD)
VRBO
From $853 per night (USD)
Expedia
Recharge @ Timberland Lodge: Pool Hottub Sauna
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Summary: Escape to Recharge @ Timberland Lodge — a bold, modern retreat in a quiet, mature neighborhood. This stylish h ...
From $853 per night (USD)
Expedia
From $312 per night (USD)
VRBO
WHEELCHAIR ACCESSIBLE 3 Bedroom 2 Bathroom Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This family home in the desirable Rolling Hills Golf community has been renovated to be completely wheelchair accessible ...
From $312 per night (USD)
VRBO
Click For Pricing
VRBO
Lakefront Studio • Breathtaking Views • Private Keyless Entry • Parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Boutique Lakefront Studio in Altamonte Springs — Designed for Solo Professionals Enjoying an Extended Central Florida St ...
Click For Pricing
VRBO
Click For Pricing
VRBO
Spacious 2BR with Open Layout
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a comfortable and stylish stay in the heart of Winter Springs. This bright, thoughtfully furnished home features a ...
Click For Pricing
VRBO
From $416 per night (USD)
Expedia
Tropical Oasis - Heated Luxury Pool - Game Room
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Summary: Whether you're on vacation with family, or traveling for work, this is your perfect home away from home! Amazi ...
From $416 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Tiny Hidden Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Hidden Tiny Cottage II Living the experience of Tiny Take it easy at this unique and tranquil getaway. You would l ...
From $126 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Enjoy your stay in our cozy 2 bedroom 1 bath Guest suite.Newly renovated space
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are in the heart of central Florida with easy Acess to shopping at the Altamonte mall , 35 min drive to the east coas ...
From $167 per night (USD)
Expedia

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Longwood Rentals

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Results: 40 Rentals