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Southernmost Point, Key West, Florida, United States of America

Southernmost Point vacation rentals

We found 2,267 vacation rentals — enter your dates for availability

Discover a selection of 2,500 vacation rentals in Southernmost Point, Key West that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $125 per night, and houses and bungalows are popular options for a stay in Southernmost Point. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Houses

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Bungalows

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Condos/Apartments

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Cottages

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Guest houses

View 31 Guest houses

Cabins

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Townhouses

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Boats

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Resorts

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Studios

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Yachts

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Hotels

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Villas

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Bed & breakfasts

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Estates

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Find the best place to stay — Southernmost Point

The Palms...A beautiful space in the perfect place.

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$312 avg/night
(50)

Key West Old Town Rental Compound - Private, Sleeps 23

Sleeps 23 · 10 Bedrooms · 4 Bathrooms
$3,799 avg/night
(3)

Historic Old Town Key West Cigarmaker's Cottage - Sleeps 4

Sleeps 4 · 3 Bedrooms · 1 Bathroom
$773 avg/night
(17)

Key West - Historic & Charming - Main House

Sleeps 8 · 4 Bedrooms · 1 Bathroom
$1,519 avg/night
(9)

Duval Balcony - Suite Mischief

Sleeps 4 · 1 Bedroom · 1 Bathroom
$449 avg/night
(36)

Old Town Key West - Historic & Charming - 2 Blks From Duval

Sleeps 5 · 2 Bedrooms · 1 Bathroom
$949 avg/night
(7)

Search 2,267 vacation rentals

Top rated rentals — Southernmost Point
Stayed Apr 2022

Perfect for a few days in Key West

The included bikes and pool were a huge plus. Situated in a very convenient location to restaurants and to-dos. The bikes made access even more convenient to Duval St and really everything we wanted to do. The rental is perfect for up to 2. Ken was a...

Mark S.
Mark S.
Stayed Apr 2022

Great stay in Key West!

This property was perfect for the price point. If you are looking for the Ritz, keep looking. It is a little dated but we did not care. Everything functioned properly and to our satisfaction. It was clean and had everything we needed. We did not coo...

Cynthia H.
Cynthia H.
Stayed Apr 2022

What a great stay!

We rented 279 with our friends for a week long birthday celebration and had such a great time! The condo was clean, well stocked, comfortable and in beautiful surroundings. We had plenty of space for 4 people and enjoyed the time on the patios. Neigh...

Terri K.
Terri K.
Stayed Apr 2022

Spring Break @ The Cigar House

The provided description, photos, and previous reviews were spot on and super helpful. Perfect amount of space for a family of 3 on spring break. The bathroom no longer has a claw foot tub shower as pictured. It is now just a large shower. The pr...

Rachel S.
Rachel S.
Stayed Apr 2022

Nice Room Great Location Great Owner

We decided to get out of town at last minute on Friday April 8th 2022 @ 3pm, checked the airline, they had 2 seats remaining on Allegiant leaving Cincinnatiat 6am the next morning, then checked vrbo for a place to stay on Duval, found this 1 bedroom ...

Brian W.
Brian W.
Stayed Mar 2022

Great Location, But…

I can’t say enough good things about the location; a block from Duval at the southernmost end, easy walking to shops and restaurants, steps away from the #11 trolley stop. We had to park on the street, and it was metered. Residential (free) parking w...

Kelly S.
Kelly S.

Ocean Shores, Washington, USA

Stayed Feb 2022

Great location

The condo is in a great location and very quiet. The downside is the pool closes at dusk so no swimming after a hot day in town. The bedrooms and bathroom are quite small. Even tho a hairdryer is not listed in the amenities this was the first VRBO th...

Patricia M.
Patricia M.
Stayed Nov 2021

Great space for a large group-

We took over all four houses. The property was spotless and nice mature landscaping. - large pool area perfect for gathering. Location is great. Steven was a very responsive host. Rooms tend to be small and closet space limited but not really a probl...

Kim P.
Kim P.
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How many vacation rentals are available around Southernmost Point, Key West?

Our 2022 property listings offer a large selection of 2,267 vacation rentals around Southernmost Point. From 846 house rentals to 57 bungalow rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses near Southernmost Point?

Yes, of course. Vrbo has 846 Houses near Southernmost Point. Our other popular types of vacation rentals near Southernmost Point include:

  • Bungalows: 57 rentals available
  • Condos/Apartments: 743 rentals available
  • Cottages: 57 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Guest houses and more.

Can I find a vacation rental with pool near Southernmost Point?

Yes, you can select your preferred vacation rental with pool among our 1,684 vacation rentals with pool available near Southernmost Point. Please use our search bar to access the selection of vacation rentals available.

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