Search Summerland Key Condo Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Summerland Key condo rentals

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (119 reviews)
"we had a wonderful room with a great location. It was too cold to use the pool, but it looked very inviting. Would definitely stay again."
United States
Richard
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access
Beachside
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
The price is €881
includes taxes & fees
11 Mar - 12 Mar
Comfortable Condo with Pool, Private Balcony, & Beach Access

Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (30 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is €718
includes taxes & fees
1 Mar - 2 Mar
Grand Marina Suite - Poolside & Waterfront Condo

Poolside Suite with Direct Pool Access

Poolside Suite with Direct Pool Access
Key West
10.0 out of 10, Exceptional, (2 reviews)
"amazing spot close to everything "
United States
Rosalina
The price is €533
includes taxes & fees
1 Mar - 2 Mar
Poolside Suite with Direct Pool Access

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Key West
9.0 out of 10, Wonderful, (137 reviews)
"Loved how convenient and quiet this place was. The balcony and view of the pool was a plus. We sat out there each morning and evening."
United States
Angela C.
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (104 reviews)
"Fabulous view to watch the sunset and planes take off! Super comfortable stay with all the typical amenities and plenty of space. Quiet location close enough to drive/bike to everything you need without all the bustle. Margaret was an amazing, communicative host. "
United States
Chloe C.
The price is €477
includes taxes & fees
23 Feb - 24 Feb
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
8.8 out of 10, Excellent, (32 reviews)
"Everything was just as advertised. Had a wonderful stay"
United States
Julie D.
The price is €648
includes taxes & fees
17 Feb - 18 Feb
The Andros | Incredible Views w/ Shared Pool

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Meadows
9.8 out of 10, Exceptional, (21 reviews)
"Really enjoyed the accommodations. "
United States
Timothy
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage
Meadows
9.6 out of 10, Exceptional, (25 reviews)
"clean and accomodating for a group of 4."
United States
N
The price is €620
includes taxes & fees
22 Feb - 23 Feb
"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (38 reviews)
"Very enjoyable other than the rooster started crowing at 4:30 AM."
United States
Carol
The price is €556
includes taxes & fees
10 Mar - 11 Mar
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Retreat to RUM CAY @ Sunrise Suites

Retreat to RUM CAY @ Sunrise Suites
Key West
9.4 out of 10, Exceptional, (14 reviews)
"Always a good time in Key West. Love this location!"
United States
Gary K.
The price is €657
includes taxes & fees
23 Feb - 24 Feb
Retreat to RUM CAY @ Sunrise Suites

Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking

Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Key West
10.0 out of 10, Exceptional, (67 reviews)
"Great view and Hospitality "
United States
Greg S.
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking

The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Every as described, great stay!"
United States
Bryan W.
The Cat Island Suite | Charmingly Renovated w/ Pool

Duval Street Suites on Duval Free Parking and heated Pool

Duval Street Suites on Duval Free Parking and heated Pool
Old Town Key West
10.0 out of 10, Exceptional, (13 reviews)
"Great location, very clean, easy checkin"
United States
Debra G.
Duval Street Suites on Duval Free Parking and heated Pool

Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"Good amenities, nice for a weekend get away"
United States
Alexander B.
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Overlook Duval St from your Cuban Club balcony

Overlook Duval St from your Cuban Club balcony
Old Town Key West
9.8 out of 10, Exceptional, (105 reviews)
"Great location would highly recommend!"
United States
Matt P.
Overlook Duval St from your Cuban Club balcony

The Caroline Suite | 1 bedroom condo w/shared pool

The Caroline Suite | 1 bedroom condo w/shared pool
Key West Historic District
8.8 out of 10, Excellent, (20 reviews)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
United States
Sean A.
The price is €467
includes taxes & fees
24 Feb - 25 Feb
The Caroline Suite | 1 bedroom condo w/shared pool

The Trinidad at Sunrise Suites - Shared Pool

The Trinidad at Sunrise Suites - Shared Pool
Key West
9.0 out of 10, Wonderful, (38 reviews)
"We enjoyed the comfortable floor plan for two couples and the convenient parking. The condo is in need of some updating and repairs but was clean with comfortable beds. "
United States
Shawna H.
The Trinidad at Sunrise Suites - Shared Pool

'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Old Town Key West
9.6 out of 10, Exceptional, (38 reviews)
"Convenient, clean….nice neighborhood."
United States
Anna H.
'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!

Dog-friendly resort condo with pool & hot tub, private parking

Dog-friendly resort condo with pool & hot tub, private parking
Key West
8.4 out of 10, Very good, (122 reviews)
"Resting well and enjoying "
United States
Bon N.
Dog-friendly resort condo with pool & hot tub, private parking
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Condo Rentals information

Number of reviews
795
Accommodation
1 Condo Rentals
Lowest Price
€467
Highest Price
€881

Frequently asked questions

Why book your condo in Summerland Key with Expedia?
Expedia makes it a cinch to find your dream condo in Summerland Key. On the lookout for a luxury escape? Take advantage of our filters to search for properties with a 5-star rating. If you have a set budget, select how much you want to spend and then browse our amazing deals. We'll help you find a suitable stay whatever your trip looks like.
How can I find cheap condos in Summerland Key?
Expedia can help you easily locate cheap condos in Summerland Key. To reserve a superb stay in a couple of clicks, simply use the filter tool to refine your search by budget, amenities and star rating.
What is there to do in Summerland Key near my condo?
The ultimate travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your sightseeing in Summerland Key.