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Guesthouse vacation rentals in Seminole County

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Top-rated guesthouse rentals in Seminole County

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

Guest favorite
Guesthouse in Sanford
Palmetto Pool Retreat
The Palmetto Pool Retreat offers complete privacy - detached studio cottage, with a pull-down Queen Murphy bed. * Kitchen - refrigerator, stove, cookware, Keurig , microwave, toaster, dishes and utensils. * Studio Living area - Queen size Murphy Bed, Roku TV, WiFi Internet, AC/Heater; Closet, Iron. Please don’t put AC lower than 72. * Private Bathroom - shower, hairdryer. *Outdoors - Solar heated pool(not propane heated) with private sitting area with 2 Fire pits Gas & Wood; BBQ Gas
Sep 12 – 19
$102 per night
Guest favorite
Guesthouse in Oviedo
Gated Luxury Country Home on Private 35 Acres
Unique 800 sq. ft standalone guesthouse on 35 private wooded acres. Relax in peace and quiet either outside with the beautiful scenery or inside with our professional GoldenWest 9' pool table. Fully furnished backyard patio with grill and smoker, firepit for cold evenings, kerosene lamps for ambiance, and lounge furniture for finishing that book you've been putting off. Conveniently located minutes away from 417, you are within reach of all that Orlando has to offer! NO CLEANING FEES!
Jul 22 – 29
$90 per night
Guest favorite
Guesthouse in Maitland
Chez Bienvenu
Close proximity to Park Avenue in Winter Park! Sunny and Adorable Vintage Guest House ...entire spacious guest house; with private entrance and driveway* Just a couple of blocks off Park Avenue to enjoy Shopping! Cafes! Museums! Nestled in quiet family community* •Smart TV •Stackable washer and dryer included in the unit. •Grill, Beach Chairs, Fishing Poles available •750 square feet of living space
Jan 3 – 10
$109 per night

Popular amenities for Seminole County guesthouse rentals

Family-friendly guest house rentals

Guest favorite
Guesthouse in Leesburg
Silver Lake Guest Pool House
Oct 28 – Nov 4
$88 per night
Guest favorite
Guesthouse in Orlando
Your Home Away From Home
Jul 12 – 19
$123 per night
Guest favorite
Guesthouse in Windermere
Small Guesthouse near Orlando's Theme Parks
Dec 25 – Jan 1
$117 per night
Superhost
Guesthouse in Mount Dora
Key West cottage of Mt Dora
Feb 8 – 15
$124 per night
Guest favorite
Guesthouse in Orlando
Private Backyard Cottage in Mills50
May 24 – 31
$85 per night
Guest favorite
Guesthouse in Orlando
Garden House near Orlando's cultural hub
Apr 5 – 12
$92 per night
Guest favorite
Guesthouse in Winter Park
WELCOME HOME IN WINTER PARK
Dec 8 – 15
$90 per night
Guest favorite
Guesthouse in Mount Dora
A Lakeshore Cottage vintage 1926
May 17 – 24
$128 per night
Guest favorite
Guesthouse in Merritt Island
Island Cottage
Jul 13 – 20
$94 per night
Superhost
Guesthouse in Clermont
Discover Tranquility at Our Charming Guest House
Sep 14 – 21
$200 per night
Guest favorite
Guesthouse in New Smyrna Beach
Newly renovated!* Downtown New Symrna Apartment
May 28 – Jun 4
$113 per night
Superhost
Guesthouse in Eustis
Relax At The Lake House
Nov 20 – 27
$139 per night

Guest house rentals with a patio

Guest favorite
Guesthouse in Lake Mary
Cozy Cottage in the heart of Lake Mary
May 13 – 20
$78 per night
Guest favorite
Guesthouse in Deltona
Krater Key Lake House
Dec 23 – 30
$95 per night
Guest favorite
Guesthouse in Sanford
Little Hidden Cottage
Sep 5 – 12
$81 per night
Guest favorite
Guesthouse in Longwood
"Winnie's Place" A Peaceful Guesthouse with Pool.
Oct 23 – 30
$110 per night
Guest favorite
Guesthouse in Lake Mary
Sunset Cottage in Lake Mary, Florida
Jul 31 – Aug 7
$110 per night
Guest favorite
Guesthouse in Altamonte Springs
Beautiful New RV Closer to Beautiful Springs Orl
Jun 10 – 17
$60 per night
Guest favorite
Guesthouse in Longwood
Cozy and Modern Studio suite in Longwood
Dec 16 – 23
$66 per night
Superhost
Guesthouse in Lake Mary
1/1 Guest house - private Escape
Jul 2 – 9
$153 per night
Guest favorite
Guesthouse in Lake Mary
Relaxing Cozy Cottage w/ Queen Bed & Private Lanai
Dec 30 – Jan 6
$137 per night
Superhost
Guesthouse in Deltona
Modern pool rental/Spring/Disney/Beach
Oct 26 – Nov 2
$87 per night
Guest favorite
Guesthouse in Longwood
Wekiva River Paradise
Sep 14 – 21
$150 per night
Guest favorite
Guesthouse in Sanford
Experience the #Sanfording House! Pool + Lanai
Apr 6 – 13
$166 per night

Guest house rentals with a washer and dryer

Guest favorite
Guesthouse in Orlando
Lakefront Seclusion modern guesthouse+Pool+Hot tub
Dec 25 – Jan 1
$189 per night
Guest favorite
Guesthouse in Orlando
Jefferson St. Cottage
Feb 6 – 13
$81 per night
Guest favorite
Guesthouse in Orlando
Bungalow Central to Downtown ORL and Winter Park🦩
Mar 30 – Apr 6
$125 per night
Guest favorite
Guesthouse in DeLand
No Worries Carriage House, 5 min walk to Stetson
May 15 – 22
$80 per night
Guest favorite
Guesthouse in Orlando
Peculiar newly built one bedroom Studio.
Jul 10 – 17
$60 per night
Guest favorite
Guesthouse in Orlando
Oasis Garden Cottage -cozy, chic, near everything!
Aug 3 – 10
$96 per night
Guest favorite
Guesthouse in Orlando
Private Luxurious Apt. - Historic Downtown Orlando
Apr 26 – May 3
$130 per night
Guest favorite
Guesthouse in Mount Dora
Mount Dora Hide-away
May 5 – 12
$85 per night
Guest favorite
Guesthouse in Orlando
8th Green Cottage - A relaxing oasis in the city
Jul 21 – 28
$117 per night
Guest favorite
Guesthouse in Orlando
Bungalow Close to Attractions and Downtown Orlando
Jan 14 – 21
$84 per night
Guest favorite
Guesthouse in Orlando
Lovely Spacious Guesthouse in Mills 50 District
Oct 28 – Nov 4
$60 per night
Guest favorite
Guesthouse in Orlando
Black House- Private Cottage in Thornton Park!
Jul 6 – 13
$166 per night

Destinations to explore