Holiday Homes in Summerland Key

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Featured Holiday Homes in Summerland Key and around

Fridge, microwave, oven, stovetop
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!
2 bedrooms, iron/ironing board, travel cot, free WiFi
Oceanside home, dock,kayaks,bikes,pool,fishing,111
10.0 out of 10, Exceptional, (149)
"This property was perfect for 2 couples of empty nesters. The condo was the best one on the property in my opinion due to the awesome views from the place. It’s also close to some great restaurants in the area. I would definitely recommend to others."
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Pool
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (38)
"We stayed 4 nights and enjoyed our stay. The place was very nice. Nicely decorated, bikes and golf cart were available. We will come again."
**MERMAID MAGIC @ VENTURE OUT** Waterfront Home & Slip + LAST KEY SERVICES…
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Aerial view
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
10.0 out of 10, Exceptional, (3)
"Wonderful experience staying here! The property was clean and even stocked with some things upon arrival (water in fridge, paper towels, dishwasher tabs, a couple laundry detergent tabs, etc) We had an amazing week and can’t thank you enough for sharing your beautiful home with us!"
WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!
Exterior
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
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
Beach
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
Exterior
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
Property grounds
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 €419
per night
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Beach nearby
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.8 out of 10, Exceptional, (18)
"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!
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
Beach towels
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
On the beach, beach towels
Beachside @ Torchview Waterfront Retreat
9.8 out of 10, Exceptional, (28)
"Great view, quiet location."
Beachside @ Torchview Waterfront Retreat
Exterior
Island Therapy
9.8 out of 10, Exceptional, (40)
"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
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, (69)
"This property had everything we wanted and more. Owners were extremely nice & helpful. "
The price is €652
per night
3 Jun - 4 Jun
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
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
A heated pool
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
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
Property grounds
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
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

Exterior
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
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
Fridge, microwave, oven, stovetop
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.

Summerland Key Holiday Homes information

Number of reviews
1,766
Accommodation
268 Holiday Homes
Lowest Price
€419
Highest Price
€1,255

Recent Reviews in Summerland Key
Expedia verified reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

5/5 Excellent
"Great place to stay!"
A verified traveller stayed at Sugarloaf Key Hotel at KOA Resort
Posted 2 days ago
Sugarloaf Key Hotel at KOA Resort