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Our top choices for Summerland Key condo rentals

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 AED 1,660
AED 3,720 total
includes taxes & fees
11 Mar - 12 Mar
Comfortable Condo with Pool, Private Balcony, & Beach Access
9.6 out of 10, Exceptional, (31 reviews)
"Good condo and staff help me out on phone with me till we found the condo. "
United States
Raamkumaran
The price is AED 1,870
AED 2,673 total
includes taxes & fees
11 Mar - 12 Mar
Grand Marina Suite - Poolside & Waterfront Condo
10.0 out of 10, Exceptional, (2 reviews)
"amazing spot close to everything "
United States
Rosalina
The price is AED 1,399
AED 2,077 total
includes taxes & fees
4 Mar - 5 Mar
Poolside Suite with Direct Pool Access
9.6 out of 10, Exceptional, (10 reviews)
"Condo was perfect for what we needed for our 1 night stay in Key West"
United States
Mika
The price is AED 1,133
AED 2,467 total
includes taxes & fees
4 Mar - 5 Mar
The Grand Cayman | Beautifully Remodeled Key West!
8.8 out of 10, Excellent, (120 reviews)
"Convenient clean and a great vacation"
United States
Michelle N.
The price is AED 771
AED 1,783 total
includes taxes & fees
12 Mar - 13 Mar
Dog-friendly condo with pool, hot tub, balcony, central AC, W/D, & fitness room
9.8 out of 10, Exceptional, (120 reviews)
"Loved our stay here! "
United States
samantha s.
The price is AED 863
AED 1,650 total
includes taxes & fees
18 Mar - 19 Mar
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
10.0 out of 10, Exceptional, (36 reviews)
"Every as described, great stay!"
United States
Bryan W.
The price is AED 1,297
AED 2,677 total
includes taxes & fees
24 Mar - 25 Mar
The Cat Island Suite | Charmingly Renovated w/ Pool
9.8 out of 10, Exceptional, (22 reviews)
"Really enjoyed the accommodations. "
United States
Timothy
The price is AED 1,928
AED 3,437 total
includes taxes & fees
22 Mar - 23 Mar
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
8.6 out of 10, Excellent, (123 reviews)
"We like this place, It was clean and quiet"
United States
Julie P.
The price is AED 683
AED 1,642 total
includes taxes & fees
4 Mar - 5 Mar
Dog-friendly suite with pool, hot tub, tennis & full kitchen
9.0 out of 10, Wonderful, (39 reviews)
"Very enjoyable other than the rooster started crowing at 4:30 AM."
United States
Carol
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Condo in Naval Air Station Key West

The Grenada at Sunrise Suites - Shared Pool
8.6 out of 10, Excellent, (11 reviews)
"Great location. Clean. Very nice all around"
United States
Mandie T.
The Grenada at Sunrise Suites - Shared Pool
8.6 out of 10, Excellent, (92 reviews)
"We had a pleasant stay"
United States
Lisa H.
The price is AED 1,139
AED 2,263 total
includes taxes & fees
4 Mar - 5 Mar
Dog-friendly condo with pool & hot tub - walk or bike to beach
8.8 out of 10, Excellent, (210 reviews)
"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "
United States
Juan E.
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
9.2 out of 10, Wonderful, (39 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
9.6 out of 10, Exceptional, (99 reviews)
"Nice property, great location, comfortable bed, lovely pool. "
United States
Candice B.
The price is AED 1,158
AED 2,022 total
includes taxes & fees
16 Mar - 17 Mar
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
8.4 out of 10, Very Good, (122 reviews)
"Resting well and enjoying "
United States
Bon N.
The price is AED 1,062
AED 2,157 total
includes taxes & fees
8 Mar - 9 Mar
Dog-friendly resort condo with pool & hot tub, private parking
9.8 out of 10, Exceptional, (26 reviews)
"This property is beautiful and the location is great as well. We will be back!"
United States
Patricia K.
The price is AED 1,221
AED 2,586 total
includes taxes & fees
19 Mar - 20 Mar
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
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
8.6 out of 10, Excellent, (144 reviews)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is AED 1,062
AED 2,183 total
includes taxes & fees
21 Mar - 22 Mar
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Condo in Old Town Key West

Leo's Lodge | Newly Updated!
8.6 out of 10, Excellent, (25 reviews)
"Very nice facility and pool; bathroom was small for large person."
United States
James
The price is AED 722
AED 1,683 total
includes taxes & fees
22 Mar - 23 Mar
Leo's Lodge | Newly Updated!
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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Top Summerland Key Hotel Reviews

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