Compare Winter Haven Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Winter Haven

Guests of Disney Proximity Escape - Comfort in Kissimmee enjoy features like an outdoor pool, free WiFi in public areas, and express check-out. Limited parking is available. Staff members can answer questions about accommodations, and also provide luggage storage.

$138 nightly

$156 total

Jul 8 - Jul 9

Total with taxes and fees

Guests of SmartStay Homes enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. If you drive, take advantage of free parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.

$96 nightly

$108 total

Jul 11 - Jul 12

Total with taxes and fees

Guests of Tempo Trek Lodgings enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. You can put free parking to good use if you drive. Staff members are on hand to provide luggage storage and access to locker space.

$124 nightly

$141 total

Aug 5 - Aug 6

Total with taxes and fees

Guests of Affordable Stays Kissimmee enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. Free parking is available if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.

Pool

Parking included

At 1580 Sandbagger Drive, guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. There's free parking if you drive. This golf guesthouse also has laundry facilities.

Pool

Hot Tub

At Blissful Bay, guests have access to an outdoor pool, free WiFi in public areas, and microwave in a common area. There's free parking if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a TV in a common area.

Guests of Jade Manor enjoy an outdoor pool, free WiFi in public areas, and microwave in a common area. If you drive, take advantage of free offsite parking. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.

The Lake Morton Loft in Historic Downtown Lakeland, FL

At this guesthouse, guests have access to features like laundry facilities.

Guests of Oasis Private Ensuite Room Shared Home enjoy features like 2 outdoor pools, free WiFi in public areas, and microwave in a common area. You can take advantage of free offsite parking if you drive. Additional amenities include a refrigerator in a common area, laundry facilities, and a communal living room.

Don't see what you're looking for?

See all available properties in Winter Haven

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Winter Haven

Holiday Inn Winter Haven by IHG

200 Cypress Gardens Boulevard Winter Haven FL

$110 nightly

$123 total

Jul 26 - Jul 27

Total with taxes and fees

9/10 Wonderful! (1,005 reviews)

Legoland Florida Hotel

1 Legoland Way Winter Haven FL

$298 nightly

$333 total

Jul 19 - Jul 20

Total with taxes and fees

8.8/10 Excellent! (152 reviews)

LEGOLAND Beach Retreat

100 Legoland Way SE Winter Haven FL

$170 nightly

$191 total

Aug 2 - Aug 3

Total with taxes and fees

8.8/10 Excellent! (289 reviews)

Winter Haven Guest Houses essential information

Accommodation	42 Guest Houses
Lowest Price	$108
Highest Price	$333
Popular accommodation	Disney Proximity Escape - Comfort in Kissimmee, SmartStay Homes, Tempo Trek Lodgings, Affordable Stays Kissimmee, 1580 Sandbagger Drive, Blissful Bay, Jade Manor, The Lake Morton Loft in Historic Downtown Lakeland, FL, Oasis Private Ensuite Room Shared Home