Guesthouse vacation rentals in Orlando

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Top-rated guesthouse rentals in Orlando

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Orlando
Lakefront Seclusion modern guesthouse+Pool+Hot tub
***Pool/Spa being serviced until 2024 March 15*** An oasis in the city is what you will be surprised to find here at your guest house, located on a peaceful estate on the shore of Lake Hourglass. Secluded from the noises of the city, but still just minutes from everything, it's the perfect base to explore Orlando from, or perhaps to enjoy a staycation at if you're a local! For check out, please just enjoy your stay with us, you don’t need do any tidy or clean steps for us.
May 21 – 28
$175 per night
4.96 out of 5 average rating, 341 reviews
Guest favorite
Guesthouse in Winter Park
Private and Peaceful with Full Kitchen
Welcome to our spacious, secure getaway tucked in a quiet Winter Park neighborhood. Enjoy full kitchen, hardwood floors, high ceilings, superfast WiFi and lots of TV steaming options, walk-in closets and walk-in shower. The hosts live in a separate space attached to the house. Your suite and patio are completely private. Please register all guests when making your reservation. For everyone’s safety, we ask that there be no visitors besides registered guests.
May 9 – 16
$85 per night
4.98 out of 5 average rating, 241 reviews
Guest favorite
Guesthouse in Orlando
Couples Oasis Heated Pool and Lake View
Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing in the patio chairs by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house.
Aug 11 – 18
$109 per night
4.87 out of 5 average rating, 202 reviews

Popular amenities for Orlando guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Orlando
Garden House near Orlando's cultural hub
Apr 20 – 27
$91 per night
4.94 out of 5 average rating, 383 reviews
Superhost
Guesthouse in Dade City
Studio Zen
May 28 – Jun 4
$61 per night
4.82 out of 5 average rating, 212 reviews
Guest favorite
Guesthouse in Winter Park
WELCOME HOME IN WINTER PARK
Aug 12 – 19
$89 per night
4.81 out of 5 average rating, 227 reviews
Guest favorite
Guesthouse in Lakeland
Modern lakeside retreat by SEU and FSC
Jun 8 – 15
$96 per night
4.98 out of 5 average rating, 206 reviews
Guest favorite
Guesthouse in Windermere
Small Guesthouse near Orlando's Theme Parks
Aug 13 – 20
$117 per night
4.94 out of 5 average rating, 233 reviews
Superhost
Guesthouse in Mount Dora
Key West cottage of Mt Dora
Jan 17 – 24
$122 per night
4.9 out of 5 average rating, 690 reviews
Superhost
Guesthouse in Clermont
Discover Tranquility at Our Charming Guest House
Jun 5 – 12
$200 per night
4.85 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Orlando
Your Home Away From Home
Mar 29 – Apr 5
$140 per night
4.99 out of 5 average rating, 193 reviews
Guest favorite
Guesthouse in Orlando
Nice Brand New Studio !!
Apr 3 – 10
$70 per night
4.84 out of 5 average rating, 313 reviews
Guest favorite
Guesthouse in Maitland
Chez Bienvenu
Nov 22 – 29
$105 per night
4.87 out of 5 average rating, 379 reviews
Guest favorite
Guesthouse in Mount Dora
A Lakeshore Cottage vintage 1926
May 17 – 24
$128 per night
4.88 out of 5 average rating, 310 reviews
Superhost
Guesthouse in Orlando
Lakefront Guest House by downtown :Boat, Fishing…
Mar 11 – 18
$120 per night
4.82 out of 5 average rating, 17 reviews

Guest house rentals with a patio

Guest favorite
Guesthouse in Maitland
Private 1-bd Mid-Century Guesthouse
Sep 10 – 17
$86 per night
4.98 out of 5 average rating, 111 reviews
Guest favorite
Guesthouse in Orlando
Charming 1 bedroom Casita with private entrance
Aug 4 – 11
$51 per night
4.96 out of 5 average rating, 167 reviews
Guest favorite
Guesthouse in Orlando
The Sacred Space Downtown Orlando Milk District
Dec 3 – 10
$90 per night
5.0 out of 5 average rating, 145 reviews
Guest favorite
Guesthouse in Orlando
Stylish Private Studio in Downtown Orlando
Apr 13 – 20
$102 per night
4.95 out of 5 average rating, 115 reviews
Guest favorite
Guesthouse in Orlando
“The Clementine” Quaint Boho Home in Local Orlando
Oct 2 – 9
$97 per night
4.87 out of 5 average rating, 112 reviews
Guest favorite
Guesthouse in Orlando
Hidden Luxury Gem w/ private porch
Apr 25 – May 2
$85 per night
4.92 out of 5 average rating, 117 reviews
Guest favorite
Guesthouse in St. Cloud
Experience FL in a Cypress Cabin w/Pool & Theater
Jul 23 – 30
$148 per night
4.95 out of 5 average rating, 128 reviews
Guest favorite
Guesthouse in Mount Dora
Enjoy downtown: modern studio w/ kitchenette
May 1 – 6
$110 per night
4.92 out of 5 average rating, 126 reviews
Guest favorite
Guesthouse in Orlando
Cozy new guesthouse to yourself.
Aug 11 – 18
$55 per night
4.94 out of 5 average rating, 33 reviews
Guest favorite
Guesthouse in Orlando
Downtown private pool house. Two blocks from ORMC
May 13 – 20
$71 per night
4.93 out of 5 average rating, 98 reviews
Guest favorite
Guesthouse in Orlando
New modern guesthouse City Center!
May 11 – 18
$105 per night
4.94 out of 5 average rating, 52 reviews
Guest favorite
Guesthouse in Orlando
Luxury studio with lake view!
Aug 4 – 11
$136 per night
4.98 out of 5 average rating, 59 reviews

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Orlando
Lovely Spacious Guesthouse in Mills 50 District
Jun 11 – 18
$63 per night
4.84 out of 5 average rating, 188 reviews
Guest favorite
Guesthouse in Orlando
Peculiar newly built one bedroom Studio.
Feb 6 – 13
$60 per night
4.97 out of 5 average rating, 241 reviews
Guest favorite
Guesthouse in Orlando
Modern Guest Studio (Private) Pool / Spa available
Sep 25 – Oct 2
$92 per night
4.96 out of 5 average rating, 204 reviews
Guest favorite
Guesthouse in Orlando
Bungalow Close to Attractions and Downtown Orlando
Aug 29 – Sep 5
$82 per night
4.89 out of 5 average rating, 369 reviews
Guest favorite
Guesthouse in Orlando
8th Green Cottage - A relaxing oasis in the city
Aug 19 – 26
$117 per night
4.9 out of 5 average rating, 136 reviews
Guest favorite
Guesthouse in Orlando
Oasis Garden Cottage -cozy, chic, near everything!
Apr 28 – May 5
$101 per night
4.97 out of 5 average rating, 279 reviews
Guest favorite
Guesthouse in Orlando
Black House- Private Cottage in Thornton Park!
Jul 8 – 15
$166 per night
4.99 out of 5 average rating, 236 reviews
Guest favorite
Guesthouse in Sanford
Palmetto Pool Retreat
Sep 16 – 23
$102 per night
4.95 out of 5 average rating, 212 reviews
Guest favorite
Guesthouse in Orlando
Bungalow Near Downtown Orlando - No Cleaning Fee!
Nov 13 – 20
$200 per night
4.92 out of 5 average rating, 225 reviews
Superhost
Guesthouse in Orlando
Cozy Guest Home 1.8 Miles from City Center
May 2 – 9
$84 per night
4.9 out of 5 average rating, 273 reviews
Guest favorite
Guesthouse in Mount Dora
The Carriage House - Walk to Downtown!!!!
May 11 – 18
$96 per night
4.97 out of 5 average rating, 159 reviews
Guest favorite
Guesthouse in Winter Haven
Quiet,Country and Close to Everything!
Nov 5 – 12
$116 per night
4.98 out of 5 average rating, 120 reviews

Quick stats about guesthouse rentals in Orlando

Total rentals

220 properties

Rentals with dedicated workspaces

110 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

17K reviews

Destinations to explore

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  4. Orange County
  5. Orlando
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