Search Cottages in Summerland Key

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Check prices for these dates

Compare 57 Cottages in Summerland Key with updated reviews, rates, and availability.

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (133)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (153)
"As always, we had a great time. Nothing fancy but just a quiet get-away. "
The price is SAR 619
SAR 1,118 total
includes taxes & fees
19 Apr - 20 Apr
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (136)
"Very nice"
The price is SAR 657
SAR 1,281 total
includes taxes & fees
17 Apr - 18 Apr
Cottage with Pool and Dockage, just minutes to Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.2 out of 10, Wonderful, (70)
"Location was right by the water. Very relaxing and quiet. Enjoyed the heated pool!"
The price is SAR 657
SAR 1,352 total
includes taxes & fees
20 Apr - 21 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.6 out of 10, Exceptional, (21)
"It was an awesome time! Pool was nice and hot with an excellent location. Hope was a great hostess and look forward to coming back sooner than later "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
The price is SAR 844
SAR 1,549 total
includes taxes & fees
21 Apr - 22 Apr
Direct Oceanfront Cottage-Sunrise View- #2,

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very Good, (39)
"Was such a great stay clean and everything we needed "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (66)
"These are great older cottages. Not luxurious, great for fishing, relaxing away from the bustle of Key West but a short drive to all the fun. Local restaurants are great Tonio's was definitely our favorite. Lobster and local fish. Skewered shimp with rice and great sauce. We had a relaxing time "
The price is SAR 657
SAR 1,352 total
includes taxes & fees
17 Apr - 18 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (111)
"30 minutes from Key West. No problems finding the place. No traffic. "
The price is SAR 619
SAR 1,258 total
includes taxes & fees
26 Apr - 27 Apr
Charming cottages, dockage, pool, just minutes to Key West

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (133)
"Had issue with tv, but host resolved quickly. Close to many places to eat."
The price is SAR 882
SAR 1,595 total
includes taxes & fees
19 Apr - 20 Apr
Quaint cottage, pool, dockage just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (81)
"We really liked the location of this rental. It is situated in a quiet community, on the beautiful canal, and close to other things in the area. We did not spend a ton of time at the house due to family events but the property had everything we needed for our short weekend trip. The only reason I gave it a 4 star is because of the air conditioning rule. The house rules state you cannot turn the AC down lower than 75 degrees, which is not a comfortable setting. "
Canal front, dockage, 2 bedroom, 2 bath

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (143)
"This little cottage was perfect for our stay. Clean and comfortable. No frills but all essentials. Property manager gave very helpful clear directions to find the cottage. Would stay again. "
The price is SAR 563
SAR 1,048 total
includes taxes & fees
16 Apr - 17 Apr
Cottage with swimming pool and dockage, just minutes to Key West!

STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

9.6 out of 10, Exceptional, (48)
"This is an awesome location. Quiet yet within 20 minutes of Key West, beaches, marinas, tiki restaurants/bars. Hope was a great host and had great suggestions on things to do and places to eat. Very pet friendly also. "
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (28)
"Very nice, location and property. The people at the park were wonderful. We joined the pancake breakfast at the shelter house and had a great time and wonderful pancakes and sausage for 6. Great deal. "
ISLE BE BACK To The Sunny Keys

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

9.8 out of 10, Exceptional, (127)
"The house was cozy and clean. Plenty of space for the two of us. We loved the back deck and patio. We enjoyed all our meals outside and used the bbq often. The location is perfect. We will definitely be back!"
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

Waterfront Home

8.8 out of 10, Excellent, (161)
"Venture out is more of a retirement community than a family resort. The location is ideal and the house was well appointed "
Waterfront Home

FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4

9.8 out of 10, Exceptional, (38)
"Great stay at the Flamingo Cottage. We were unable to get the TV to work and it was March Madness so we were in distress! Two of the owners came over within minutes and got the tournament on!! Hope gave us good recommendations on places to eat. Great location...easy drive to Key West. We used the pool and beach chairs and umbrella are available as well."
FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4

10.0 out of 10, Exceptional, (42)
"My partner and I loved staying at Palm Cottage for 5 nights. Hope was available as needed, shared information on restaurants, etc and we had everything we needed. The pool was clean and very nice, also. The location at Summerland Key was very quiet and convenient to Key West as well as Bahia Honda State Park. Appreciated having use of beach chairs and towels for the beach. We definitely would like to return! "
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4

NAUTILUS...ocean front cottage retreat ~

8.4 out of 10, Very Good, (5)
"Great property and location. Very clean. Had everything we needed- kitchen, bath , towels, kayaks and bikes. Venture Out is the resort property- nice pool, hot tub, community store. Everyone was very friendly and helpful. I almost forgot about Pickleball, Tennis and basketball court. Equipment available on loan to use- so convenient!!"
NAUTILUS...ocean front cottage retreat ~
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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Other property types in Summerland Key

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
The price is SAR 844
SAR 1,549 total
includes taxes & fees
21 Apr - 22 Apr
Direct Oceanfront Cottage-Sunrise View- #2,

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (133)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (136)
"Very nice"
The price is SAR 657
SAR 1,281 total
includes taxes & fees
17 Apr - 18 Apr
Cottage with Pool and Dockage, just minutes to Key West
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.