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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 357 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (140)
"We fell in love with this property upon our arrival and during our stay! It was very comfortable and the large screened in porch with a view of the Atlantic was one of the stars of our stay during breakfast sipping coffee in the morning and cocktails in the evening. We enjoyed the peacefulness while we relaxed at the pool. We had two minor issues and after contacting the property manager they were fixed within the hour. We definitely would stay here again."
The price is SAR 1,125
SAR 2,343 total
includes taxes & fees
25 Apr - 26 Apr
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (134)
"My sister and friend from north Alabama and my youngest daughter and I decided on a last minute mini vacation. We found this little gem of a place while looking for places to stay in the Keys. Although it could use some TLC, we found the property to be clean, well-stocked and perfect for a short stay, some family time, rest and relaxation. We truly enjoyed our stay and would definitely consider staying here again,"
The price is SAR 1,032
SAR 2,260 total
includes taxes & fees
2 Apr - 3 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (87)
"Nice property. We enjoyed our stay."
Private Secluded Ocean View & Pool Near Key West
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Shower, hair dryer, towels

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.4 out of 10, Exceptional, (30)
"Property exceeded expectations, and the view was spectacular! Absolutely would recommend staying here. It has everything you need for a comfy stay. "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (71)
"We really enjoyed our short stay in your cute cottage style home. Great views of the water and comfortable, pretty decor. What a nice surprise Kiki Sand Bar restaurant was! Overall very nice, relaxing couple of days. "
Old Florida Style, wrap around porch, boat basin for dockage, open water
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (59)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is SAR 2,622
SAR 5,697 total
includes taxes & fees
22 Apr - 23 Apr
One of the very few beach houses with a daily, rental license in the Keys.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very Good, (104)
"Definitely need to update the property. Day to day cleanliness was good but many burnt out light bulbs or mismatched bulbs. A coat of paint and updated furniture would help. House A has no view of the water and may have chosen a different place in the complex if i had known. Pool was well taken care of and lots of privacy by the home. Convenient to Key west and lots of good local restaurant choices. Beds were very comfortable. "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (211)
"We loved our stay here! This place had everything that we needed. The resort was safe for my kids to roam around for pickleball, swimming, and fishing. Thank you!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Keys Time #437 - Cudjoe Key, Oceanfront Community
A heated pool

Keys Time #437 - Cudjoe Key, Oceanfront Community

9.4 out of 10, Exceptional, (21)
"We enjoyed our stay. It fit our family of 5 well. The host was very prompt with answering any questions we had. "
The price is SAR 1,093
SAR 2,456 total
includes taxes & fees
5 Apr - 6 Apr
Keys Time #437 - Cudjoe Key, Oceanfront Community
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.8 out of 10, Excellent, (77)
"The house was very clean. The pool was heated and clean. Great views. You have to share the dock and pool with the other guests. Need to bring your own pool towels. Two out of the three beds are not comfortable. There are things in the house that need fixing. The shower door in the bathroom comes off the track if you try to open it a certain direction. So had to step out of the shower next to the toilet. Danger of falling. The shower door in the master bathroom doesn't close right. ...
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Relax by Florida Keys Beaches, just a 7-min drive away
Beach

Relax by Florida Keys Beaches, just a 7-min drive away

9.8 out of 10, Exceptional, (190)
"30 minutes to Key West; great local restaurants (highly recommend the Square Grouper) and within minutes of biking/walking trails. A wonderful location and a well appointed house. We loved it!"
Relax by Florida Keys Beaches, just a 7-min drive away
Mahi House #440 - 35' seawall
A heated pool

Mahi House #440 - 35' seawall

The price is SAR 1,289
SAR 2,704 total
includes taxes & fees
1 Apr - 2 Apr
Mahi House #440 - 35' seawall
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Miscellaneous

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.6 out of 10, Exceptional, (116)
"Spent a wonderful week here with our teen daughter. Loved having the option of riding bikes down to the pool. The location was perfect, right between Key West and Marathon Key. We found fun adventures within a short drive each day. Also enjoyed getting to know other people who were staying in the gated community resort! We’d love to come back!"
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Reel Island Retreat #273 at Venture Out in the Florida Keys
A heated pool

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.0 out of 10, Wonderful, (2)
"The property was extremely clean. It was a nice location easy to get to everything we wanted to do. The only thing we found lacking was a king bed was in the listing turned out. It was a trundle bed with king sheets. That was very disappointing as it is not comfortable for two adult adults to sleep on a trundle bed together Ended up using the second bedroom to sleep."
The price is SAR 994
SAR 2,304 total
includes taxes & fees
21 Apr - 22 Apr
Reel Island Retreat #273 at Venture Out in the Florida Keys
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (88)
"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."
The price is SAR 934
SAR 2,114 total
includes taxes & fees
31 Mar - 1 Apr
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
TV

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

9.6 out of 10, Exceptional, (64)
"Perfect property for a week away. Plenty to keep everyone happy."
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes included
A heated pool

Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes included

2.0 star property
8.6 out of 10, Excellent, (4)
"We had a very nice stay in this community. It was nice to come back to after sightseeing all day. We were close to all the activities. So nice to have a full kitchen and two bedrooms."
The price is SAR 1,093
SAR 2,426 total
includes taxes & fees
30 Mar - 31 Mar
Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes included
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Marina

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (220)
"The property had everything we needed and was very comfortable. Loved the area underneath the home. Great place to relax.The hosts were quick to respond to any question we had."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Sunny Gens - Venture Out #606
Smart TV, table tennis

Sunny Gens - Venture Out #606

Sunny Gens - Venture Out #606
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,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (171)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is SAR 656
SAR 1,311 total
includes taxes & fees
9 Apr - 10 Apr
Direct Oceanfront Cottage-Sunrise View- #2,
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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!"
The price is SAR 563
SAR 1,070 total
includes taxes & fees
8 Apr - 9 Apr
Cottage with Pool and Boat Dockage just minutes to Key West!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (71)
"We really enjoyed our short stay in your cute cottage style home. Great views of the water and comfortable, pretty decor. What a nice surprise Kiki Sand Bar restaurant was! Overall very nice, relaxing couple of days. "
Old Florida Style, wrap around porch, boat basin for dockage, open water
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.