Search Holiday Homes in Summerland Key

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Find properties with these dates

Tonight
May 11 - May 12
Tomorrow
May 12 - May 13
Next weekend
May 17 - May 19

Browse Select Summerland Key Holiday Homes

Outdoor dining
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
Beach
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
9.8 out of 10, Exceptional, (166)
"The resort was well kept and the security team was very welcoming and helpful. We stayed right on the water and had a great time."
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification
Balcony
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
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Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (216)
"Beautiful house in a gated community. Comfortable beds and a well stocked kitchen. 35 min to Key West, close to beaches and great restaurants nearby. We would not hesitate to stay here again!"
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
A heated pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (182)
"Was a super comfortable place to stay that was centrally located. The place had many amenities that we never had time to use. Thanks for such a great place"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (201)
"The property and townhouse were all very nice. If your wanting to go to Key West multiple times during the week, this location is a quick 21 miles. Townhouse was very accommodating for two couples. Pool and tiki patio areas were all clean, plenty of seating, and quiet. Only con would be bicycles need attention due to flat tires. We would book this property in the future."
The price is £362
includes taxes & fees
30 May - 31 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Exterior
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."
One of the very few beach houses with a daily, rental license in the Keys.
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (43)
"Great quiet location on the water. Quick communication with the property manager and easy check in and check out process. Definitely recommend it."
Old Florida Style, wrap around porch, boat basin for dockage, open water
Outdoor dining
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
Beach
Enjoy Caribbean weather. Last minute opening beginning 5/2/24! Enjoy the Keys!
9.4 out of 10, Exceptional, (124)
"The"
Enjoy Caribbean weather. Last minute opening beginning 5/2/24! Enjoy the Keys!
A heated pool
Island Therapy
9.8 out of 10, Exceptional, (39)
"My family and I had a wonderful time here. There is a lot to do in the neighborhood when you aren't out in the water. I would stay hear again!!"
Island Therapy
Pool
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!
Pool
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
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
10.0 out of 10, Exceptional, (194)
"The property was exactly as advertised. It was very clean and had everything we needed for our stay. Perfect for 2 couples."
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Fridge, microwave, oven, stovetop
Waterfront Beach House with Dock & Heated Pool!
10.0 out of 10, Exceptional, (68)
"Wasnt sure on reclining process"
Waterfront Beach House with Dock & Heated Pool!
Outdoor pool, a heated pool
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (68)
"The house was just as advertised. It was beautiful and the host were great."
The price is £563
includes taxes & fees
3 Jun - 4 Jun
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
Pool
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (37)
"This was the perfect family getaway for a few days. The beds were really comfy. I loved relaxing on the deck in the morning to drink my coffee in the sun, the pool area was great and having the golf cart was icing on the cake. If your looking for a nice comfortable getaway check out the mermaid condo"
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
Fridge, microwave, oven, stovetop
Dickey's Dockside Retreat
10.0 out of 10, Exceptional, (1)
"What a way to check out of the weather up north and check into paradise - that's exactly what we did. We'll be back next year."
Dickey's Dockside Retreat
Outdoor pool, a heated pool
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
10.0 out of 10, Exceptional, (4)
"My husband and i had a wonderful time. The home is large and just like the pictures. The pool is heated and just what you needed after a day of fishing. If you like to walk there is a walking path across the street."
Pool, tiki hut, easy ocean access canal, dock, prime location 30m to Key West
A heated pool
3 night minimum! Spectacular Ocean Views!
8.2 out of 10, Very good, (15)
"Unit was slightly smaller than what we were expecting by the pictures. Very clean, except for the floor in main area. Walking around left the soles of your feet very dirty. Used mop that was provided and it cleaned up nicely. When roll-out bed was out, there was no room to maneuver in the room. Everything worked as expected. Neighborhood was quiet and nice. Manager was responsive and very helpful. A lot of amenities were provided and appreciated."
3 night minimum! Spectacular Ocean Views!
Don't see what you're looking for?
See all available properties in Summerland Key
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

Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.2 out of 10, Wonderful, (63)
"Resorts was great love the pool and water....home was clean nice bedrooms and baths really small but we just sleep in them. Deck was great. To be in early morning watching sun rise..."
Canal front, dockage, 2 bedroom, 2 bath
Outdoor dining
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
Waterfront Home
8.8 out of 10, Excellent, (141)
"Would definitely come back!!!!"
Waterfront Home
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.