Book Guest Houses in Winter Haven, FL

Seize Your Someday with our amazing deals for the whole family!

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Top Guest Houses in Winter Haven

Disney Proximity Escape - Comfort in Kissimmee

Disney Proximity Escape - Comfort in Kissimmee

3 out of 5
286 Marcello Blvd Kissimmee FL
Get rates
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and express check-out. Luggage storage and a virtual front desk are also provided.
Pool
Free WiFi
Serenity Dreams

Serenity Dreams

3 out of 5
6120 Broad Oak Dr Davenport FL
$124 nightly
The price is $138 total per night
$138 total
Sep 4 - Sep 5
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Tempo Trek Lodgings

Tempo Trek Lodgings

3 out of 5
7324 Oakmoss Loop Davenport FL
$100 nightly
The price is $112 total per night
$112 total
Aug 26 - Aug 27
Total with taxes and fees
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. Luggage storage, locker space, and a virtual front desk are also on offer.
Pool
Parking included
SmartStay Homes

SmartStay Homes

3 out of 5
225 Marcello Boulevard Kissimmee FL
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
1580 Sandbagger Drive

1580 Sandbagger Drive

3 out of 5
1580 Sandbagger Dr Four Corners FL
Get rates
This guesthouse features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. Laundry facilities are provided for your convenience.
Blissful Bay

Blissful Bay

3 out of 5
4453 Monado Dr Kissimmee FL
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room is also provided.
Affordable Stays Kissimmee

Affordable Stays Kissimmee

3 out of 5
266 Marcello Blvd Kissimmee FL
Get rates
An outdoor pool, free self parking, and laundry facilities are featured at this guesthouse. WiFi in public areas is free. A communal living room and a virtual front desk are also provided.
Pool
Parking included
Disney-Area 3BR Home | Pool, Arcade and Tiki Bar

Disney-Area 3BR Home | Pool, Arcade and Tiki Bar

Davenport FL
Get rates
Stay at this guesthouse in Davenport. Enjoy an in-room coffeemaker. Popular attractions Disney's Animal Kingdom® Theme Park and Mystic Dunes Golf Club are located nearby.
Jade Manor

Jade Manor

2 out of 5
6122 Broad Oak Dr Davenport FL
Get rates
An outdoor pool is featured at this guesthouse, along with free WiFi in public areas and a communal living room. Laundry facilities and a virtual front desk are also provided.
Oasis Private Ensuite Room Shared Home

Oasis Private Ensuite Room Shared Home

2 out of 5
227 Marcello Blvd Kissimmee FL
Get rates
This guesthouse features 2 outdoor pools, free WiFi in public areas, and a communal living room. Laundry facilities and a virtual front desk are also provided.
The Lake Morton Loft in Historic Downtown Lakeland, FL

The Lake Morton Loft in Historic Downtown Lakeland, FL

Lakeland FL
Get rates
This guesthouse features laundry facilities.
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL

Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL

Winter Haven FL
Get rates
This guesthouse features laundry facilities.
Free WiFi
Air conditioning
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.

Top hotels in Winter Haven

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

305 5th St NW and Avenue D NW Winter Haven FL
$103 nightly
The price is $115 total per night from Aug 30 to Aug 31
$115 total
Aug 30 - Aug 31
Total with taxes and fees
9.8/10 Exceptional! (877 reviews)

Winter Haven Guest Houses essential information

Accommodation
46 Guest Houses
Lowest Price
$95
Highest Price
$255
Popular accommodation
Disney Proximity Escape - Comfort in Kissimmee, Serenity Dreams, Tempo Trek Lodgings, SmartStay Homes, 1580 Sandbagger Drive, Blissful Bay, Affordable Stays Kissimmee, Disney-Area 3BR Home | Pool, Arcade and Tiki Bar, Jade Manor, Oasis Private Ensuite Room Shared Home, The Lake Morton Loft in Historic Downtown Lakeland, FL, Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL

Explore More Ways to Travel with Travelocity