Sunnyside Up

Name: Sunnyside Up
Address: Key West, Florida, Key West, Monroe County, US
Price range: $739–$1,876 per night
Rating: 9.52

From

$711

/ night

Select dates to see prices and availability

From

$711

/ night

About this property

Close to cycling, fishing, and more, this pet-friendly apartment brings it all within reach. Key West Firehouse Museum is just steps away and Florida Keys Beaches is within an easy 7-minute walk, so leave your car at the property, which off...

Parking
Swimming pool
Garden
Golf Course (nearby)
Cycling
Fishing

Show all

Location

Key West, Florida

More location info

Guest reviews

9.5

Exceptional

Based on 91 verified reviews

10

Wendy J.

Aug 31, 2025

·

Stayed 3 nights

We had an awesome stay. The property managers were very responsive. This was a last minute decision and everything went smoothly. The place was clean and had everything you could need. It was a convenient location. The beds were so comfortable! Would definitely stay again.

10

Peggy S.

Jan 6, 2025

·

Stayed 7 nights

Clean home with lovely outdoor area and pool. Just up the street from the Southernmost point... just lovely. Everything was as described...

10

Miguel T.

Oct 21, 2024

·

Stayed 3 nights

Was amazing the house and very great location

10

Hunter H.

Sep 16, 2024

·

Stayed 2 nights

Great location and very quiet, good communication made it easy to check in and out of the place.

10

Heather M.

Jan 26, 2024

·

Stayed 3 nights

There were 9 adult females and this house had plenty of space for all of us to sleep and get ready for nights out! Pool was clean and nice to lay out around. Too cold to swim in January but everything was great!

Property Policies

Check-in instructions

Everything you need to know for a smooth check-in.

Check-in

Check-out

From 16:00 to 18:00

Before 10:00

Good to know

Additional policies and info about this property.

FAQs about Sunnyside Up

Is parking available at the property?

Yes, the property offers covered onsite parking, which is free of charge.

Does the property allow pets?

Yes, the property is pet-friendly. Specific pet policies, including maximum number and fees, are not detailed.

What are the check-in and check-out times?

Check-in is from 4:00 PM to 6:00 PM, and check-out is at 10:00 AM. Early or late check-in/check-out options are not specified.

Where is the property located?

The property is located in Old Town Key West, within walking distance to notable landmarks such as the Southernmost Point and Ernest Hemingway Home and Museum. Florida Keys Beaches is about a 7-minute walk away.

Does the property have a swimming pool?

Yes, there is a communal outdoor pool available for guests.

What are the policies for guests staying with children?

Children are allowed at the property, and specific age policies for free stays are not detailed.

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Prices for upcoming dates

September 2026

Su	Mo	Tu	We	Th	Fr	Sa
		1	2	3	4	5
6	7	8	9	10	11	12
13	14	15	16 $760	17 $794	18 $931	19 $971
20 $767	21 $817	22 $765	23 $759	24	25	26
27 $791	28 $739	29 $822	30 $829

October 2026

Cheaper

Pricier

Average nightly price across deals, with taxes & fees.

Prices in USD for 2 guests, updated daily.

Sunnyside Up

Select dates to see prices and availability

About this property

Location

Location

Room options

Holiday Home

Guest reviews

Exceptional

Property Policies

Check-in instructions

Good to know

FAQs about Sunnyside Up

Have a question?

Prices for upcoming dates

Product

Company

Contact

Social

Popular amenities

Activities

Parking

Internet

Su	Mo	Tu	We	Th	Fr	Sa
				1	2	3
4	5 $808	6 $814	7 $836	8 $937	9	10
11	12 $911	13 $1,160	14 $867	15 $1,014	16	17
18 $1,573	19 $1,339	20 $1,478	21 $1,876	22	23	24
25 $1,113	26	27 $1,102	28 $964	29 $1,218	30	31