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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Summerland Key villas

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

1. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is ￥82,138
￥154,901 total
includes taxes & fees
Nov 15 - Nov 16
Atlantic View Luxury Villa with Pool
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

2. Poolside King Room Steps from Duval!

Poolside King Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
United States
Michael L R.
The price is ￥52,219
￥63,350 total
includes taxes & fees
Nov 23 - Nov 24
Poolside King Room Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

3. Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (4 reviews)
"Great location, great hosts, would definitely stay here again."
United States
Ryan C.
The price is ￥42,696
￥51,684 total
includes taxes & fees
Nov 18 - Nov 19
Poolside Queen Room Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

4. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay"
United States
Benjamin K.
The price is ￥47,457
￥57,517 total
includes taxes & fees
Nov 22 - Nov 23
Poolside Studio Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

5. One Bedroom Deck Villa Steps from Duval!

One Bedroom Deck Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (10 reviews)
"This place was great one of the best host I’ve ever had!!"
United States
Donnie S.
The price is ￥55,393
￥66,603 total
includes taxes & fees
Nov 15 - Nov 16
One Bedroom Deck Villa Steps from Duval!
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

6. Beachfront Villa on a Private Florida Keys Beach

Beachfront Villa on a Private Florida Keys Beach
Marathon
The price is ￥120,905
￥147,378 total
includes taxes & fees
Nov 18 - Nov 19
Beachfront Villa on a Private Florida Keys Beach
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

7. Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (66 reviews)
"We had a awesome time in Key West Villas. we will go back some time."
United States
Brian H.
The price is ￥87,137
￥105,490 total
includes taxes & fees
Nov 16 - Nov 17
Two Bedroom Two Bath Poolside Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

8. Loft Villa Steps from Duval!

Loft Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (22 reviews)
"The complimentary breakfast and happy hour was great! The pool and hot tub were wonderful "
United States
Linda W.
The price is ￥55,393
￥67,080 total
includes taxes & fees
Nov 15 - Nov 16
Loft Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

9. Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (47 reviews)
"Perfect location and addition of happy hour and breakfast was a big bonus!"
United States
Lynn B.
The price is ￥91,899
￥111,323 total
includes taxes & fees
Nov 23 - Nov 24
Two Bedroom Two Bath Balcony Villa Steps from Duval!
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

10. Waterfront Villa w/ Uninterrupted Ocean Views

Waterfront Villa w/ Uninterrupted Ocean Views
Marathon
The price is ￥99,379
￥117,840 total
includes taxes & fees
Nov 18 - Nov 19
Waterfront Villa w/ Uninterrupted Ocean Views
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

11. Beachfront Villa w/ Ocean-View Balcony in the Keys

Beachfront Villa w/ Ocean-View Balcony in the Keys
Marathon
The price is ￥117,318
￥142,983 total
includes taxes & fees
Nov 18 - Nov 19
Beachfront Villa w/ Ocean-View Balcony in the Keys
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

12. Waterview Villa w/ Full Kitchen in the Keys

Waterview Villa w/ Full Kitchen in the Keys
Marathon
The price is ￥92,204
￥109,371 total
includes taxes & fees
Nov 18 - Nov 19
Waterview Villa w/ Full Kitchen in the Keys
A resort with a central pool, surrounded by manicured lawns and palm trees, with a view of the ocean.

13. Waterview Villa w/ Full Kitchen & Beach Access

Waterview Villa w/ Full Kitchen & Beach Access
Marathon
The price is ￥90,410
￥107,014 total
includes taxes & fees
Nov 15 - Nov 16
Waterview Villa w/ Full Kitchen & Beach Access
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.
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Learn more about Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favorite seafood shacks serving fresh-caught Keys lobster.

See all hotels in Summerland Key
A coastal pier extending into the sea, surrounded by rocky shores and greenery.

Frequently Asked Questions

Why book your villa in Summerland Key with Expedia?

Use Expedia to find your dream villa in Summerland Key. Traveling with the family? Make the most of our filters to search for stays with amenities like a pool. If you have a fixed budget, click on how much you'd like to spend and your preferred star rating. We'll help you find the perfect fit that matches your taste and style.

How can I find cheap villas in Summerland Key?

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What is there to do near my villa in Summerland Key?

The ultimate travel accessory is a well-planned schedule. Florida Keys Beaches is a good spot to kick off your exploration of Summerland Key.