Search Vacation Homes in Summerland Key

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Compare 235 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Property grounds
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Exterior
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (184)
"Rich and Laura provided a wonderful property for our stay in the Keys. It was a quick and enjoyable 30-minute drive to Key West. The resort was beautiful and we could see the canals and a quick golf cart ride to the big water. Wish we could have stayed longer. If I dreamed up the perfect beach house, this would be it! And we had the most delicious key lime pie! Thank you Rich and Laura!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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Property grounds
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (168)
"We had a awesome family time there, everything is pretty and cute. We fishing behind the house, funny time. Everything was perfect to me and my family. Thank you!"
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Front / Side View of home
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Relax on the little sandy beach.
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (203)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is AED 1,286
AED 1,630 total
includes taxes & fees
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Oceanfront home with private pool, boat dock, kayaks, and private beach
9.4 out of 10, Exceptional, (72)
"My husband and I enjoyed the view this home has. They had everything we needed...access to the water, kayaks, grill, pleanty of towels, coconuts (fall from the tree make for an extra treat our son had so much fun with). It was a nice retreat close enough to Key West. This place had great outdoor space, very relaxing and a fun place to be."
Oceanfront home with private pool, boat dock, kayaks, and private beach
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (47)
"Layout of house and location are perfect. The owners were very communicative and responsive."
The price is AED 2,200
AED 4,878 total
includes taxes & fees
28 May - 29 May
One of the very few beach houses with a daily, rental license in the Keys.
Your porch overlooking the open water
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (168)
"Property and property owner were great. Nice quiet place for relaxation."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Exterior
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (124)
"Great stay. Comfy beds. Everything you need."
Enjoy Caribbean weather. Last minute opening beginning 5/19/24! Enjoy the Keys!
Awesome sunrise October
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, (90)
"Location and outdoor living space was awesome!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Cozy decor
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, (19)
"We absolutely loved our stay at Coconut Telegraph! We plan to return next year. The place is even better than described on VRBO and it is LITERALLY on the beautiful aqua blue water! The pool is plenty big and we enjoyed the tiki huts along the shoreline. The security team does an excellent job. It was very quiet at night. Easy drive to Key West if that is of interest. We did not use the concierge service so cannot comment except to say they had a lot to offer! Local restaurants are excellent. If...
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Direst access to the open water
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
9.8 out of 10, Exceptional, (98)
"Everything was perfect, the house was beautiful and well stocked. We even saw two manatees hang out right in front of the house for about an hour! The location is great and the host was extremely helpful. Side note, the Square Grouper restaurant, which is just down the road, was one of the best places we ate in the Keys!"
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Property grounds
FLAMINGO COTTAGE UNIT #1
9.6 out of 10, Exceptional, (24)
"Host was very nice and offered us advice on places to visit. Pool was clean and so warm. Grand daughter loved pool. Also, what was great is that your pet is allowed to stay in room with you. Very quiet area."
FLAMINGO COTTAGE UNIT #1
Shared pool
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
9.0 out of 10, Wonderful, (60)
"Overall, its a great location, the communication was key, the stay was fantastic, the house was outdated and a few minor obstacles but we made the BEST of everything. We wanted relaxation and thats what we got. Thank You for your hospitality and comforting home!"
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
9.8 out of 10, Exceptional, (59)
"The place was clean and as described also the community was clean with 24/7 security. Nice pool for kids, Nice location between Marathon and Key West. My wife and kids were very happy and we had a great time! Thank you!!"
Beautiful Ocean view with 35' private seawall, 80' Heated Pool, Hottub
Property grounds
Beachside @ Torchview Waterfront Retreat
9.8 out of 10, Exceptional, (28)
"Great view, quiet location."
Beachside @ Torchview Waterfront Retreat
Barry Beach dock for fishing/snorkeling and pool for relaxing.
Waterfront Beach House with Dock & Heated Pool!
10.0 out of 10, Exceptional, (69)
"Instalaciones perfectas, todo limpo y bello. Atención constante a todas nuestras necesidades y la zona muy buena tambien. Sin dudas volveriamos a repetir. Gracias"
Waterfront Beach House with Dock & Heated Pool!
Exterior
Island Therapy
9.8 out of 10, Exceptional, (41)
"The good: 1) The place was clean. 2) The kitchen had all the essential tools and utensils. We cooked and grilled. 3) Seawall comfortably accommodated my brother-in-law's 30 ft. tritoon. 4) Fish cleaning table was very convenient but bring your own fillet/boning knife. Theirs is duller than an opera. 5) Large washer and dryer with detergent and softener were very convenient. 6) Covered patio was a great place to have our meals or just to hang out. 7) Plenty of linens and towels. The not so...
Island Therapy
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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.

Other property types in Summerland Key

Property grounds
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Exterior
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (53)
"It was a nice Key West cottage with beautiful views of Cudjoe Bay."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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.

Recent reviews of Summerland Key hotels
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