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Check prices for these dates

Next weekend
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 Jum. I

Compare 350 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

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
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
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
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
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)
"The property was in a great spot. Relatively shot drives to Key West, Big Pine, and Bahia Honda. Getting in and out of the gated community was no problem and the house was exactly as we expected based on the pictures and description."
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
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%"
One of the very few beach houses with a daily, rental license in the 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 2,103 total
includes taxes & fees
31 Mar - 1 Apr
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Ocean Front - Private 56' Dock
Terrace/patio

Ocean Front - Private 56' Dock

9.8 out of 10, Exceptional, (138)
"Very clean cottage right on the corner of the harbor and the canal. Wonderful views!"
The price is SAR 1,282
SAR 2,996 total
includes taxes & fees
29 Mar - 30 Mar
Ocean Front - Private 56' Dock
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
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 2,297 total
includes taxes & fees
11 Apr - 12 Apr
Reel Island Retreat #273 at Venture Out in the Florida Keys
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!
Waterfront Captain House with Boat Basin & Ramp!
Outdoor dining

Waterfront Captain House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (7)
"Beautiful property comfortable beds! We enjoyed fishing in the lagoon. This is a beautiful home!"
Waterfront Captain House with Boat Basin & Ramp!
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, (70)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
Old Florida Style, wrap around porch, boat basin for dockage, open water
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)
"The location and ambiance of the property is wonderful. The house itself could use some TLC and attention to detail. It was difficult to find because there is no number on the house and Google maps was confused. There are loose and damaged faucets, burnt out light bulbs, missing fan blades, minimal towels, and no hooks in the bathroom to hang your robe or clothes on when you shower. Most repairs could be done quickly and inexpensively and would greatly enhance the stay."
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (237)
"We loved our stay. Our friends took us out to the Gulf and Atlantic almost every day. It was a lovely stay. Our kids loved the bikes and pool. We enjoyed the hot tub. We hope to be back soon! "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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!
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
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)
"Two families staying at neighboring properties and we had a n8ce stay in this quiet neighborhood."
The price is SAR 1,093
SAR 2,449 total
includes taxes & fees
31 Mar - 1 Apr
Salty Dog Shack #335 - Ocean Views! Kayaks & Bikes included
Waterfront Anchor House with Boat Basin & Ramp!
Sun loungers, beach towels

Waterfront Anchor House with Boat Basin & Ramp!

9.6 out of 10, Exceptional, (15)
"Very pleasant host and property manager. 4 bedroom and bathroom layout was awkward but we worked it out. Well equipped kitchen . Overall great time ."
Waterfront Anchor House with Boat Basin & Ramp!
Canal front home @ Venture Out Resort in the Florida Keys!
Exterior

Canal front home @ Venture Out Resort in the Florida Keys!

9.4 out of 10, Exceptional, (38)
"Very nice over all good stay no complaints. "
Canal front home @ Venture Out Resort in the Florida Keys!
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 1,299 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!
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor pool

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

8.8 out of 10, Excellent, (151)
"Cottage 1 was right by the water. A walk down a long path to a dock was a nightly trip to watch the sunset. Located between Marathon Key and Key West was perfect for restaurants and stores without the crowding from tourists. About 20-30 minutes to Key West"
The price is SAR 619
SAR 1,144 total
includes taxes & fees
7 Apr - 8 Apr
Private Oceanfront Cottage with dockage, pool 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.