Search Vacation Homes in Summerland Key

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Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
In one month
Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Vacation Homes in Summerland Key

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Miscellaneous

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

9.6 out of 10, Exceptional, (54)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
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, (224)
"Our family of 4 had a great time at this property, The house was clean and well equipped. The pool was closed during our stay, but we enjoyed the tennis courts, rec center, and bikes.The location was peaceful and centrally located to explore Key West and the Middle Keys. We would stay here again!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Miscellaneous

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

9.8 out of 10, Exceptional, (8)
"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"
$821 nightly
The price is $912
Jul 7 - Jul 8
Total includes taxes and fees
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community
Fandango - private pool
Pool

Fandango - private pool

9.6 out of 10, Exceptional, (79)
"We had a group of 12 family members ages 8-55. Everyone liked the location, view, private beach, kayaks, and also snorkeling and fishing from the private dock. "
Fandango - private pool
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, (84)
"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "
$672 nightly
The price is $745
Jul 15 - Jul 16
Total includes taxes and fees
Oceanfront home-shared swimming pool, dockage-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

8.2 out of 10, Very Good, (92)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Miscellaneous

Mini lobster available! Open Water View from porch , dock, bikes, kayaks

9.8 out of 10, Exceptional, (119)
"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!"
Mini lobster available! Open Water View from porch , dock, bikes, kayaks
Lower Keys paradise
Outdoor pool, a heated pool

Lower Keys paradise

10.0 out of 10, Exceptional, (34)
"The property was very clean and comfortable. We had a great stay "
Lower Keys paradise
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, (75)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
$800 nightly
The price is $888
Aug 2 - Aug 3
Total includes taxes and fees
Old Florida Style, wrap around porch, boat basin for dockage, open water
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, (248)
"Had a great time at the property many amenities to enjoy. Perfect location to bounce from key to key would definitely come back again."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oasis - Ocean view with pool and hot tub
Pool

Oasis - Ocean view with pool and hot tub

9.0 out of 10, Wonderful, (28)
"Nice place could use some maintenence but great location & view"
Oasis - Ocean view with pool and hot tub
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
A heated pool

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.4 out of 10, Exceptional, (3)
"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "
$556 nightly
The price is $617
Jul 6 - Jul 7
Total includes taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
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!

9.6 out of 10, Exceptional, (37)
"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!
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, (94)
"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."
$479 nightly
The price is $532
Jul 23 - Jul 24
Total includes taxes and fees
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
6 Bedroom 4 bath<br>Rental Rates are based on the number of guests
Pool

6 Bedroom 4 bath<br>Rental Rates are based on the number of guests

9.4 out of 10, Exceptional, (84)
"We have stayed here 4 times. Great house . Nice to see some renovation/ improvements made. Kitchen has everything you need for cooking. New mattress were great. Plenty of outdoor activities. Great place to chill either by pool or on lania. "
6 Bedroom 4 bath<br>Rental Rates are based on the number of guests
Kelly's Kabin - Adorable Private Summerland Key Cottage
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

9.8 out of 10, Exceptional, (117)
"This was our second time staying here. Feels very secluded although it's right off the highway. We saw many Key deer on our way to No Name Pub , including babies who thougt we should feed them) (We did not feed them). Highly recommend!"
$466 nightly
The price is $517
Jul 11 - Jul 12
Total includes taxes and fees
Kelly's Kabin - Adorable Private Summerland Key Cottage
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, (225)
"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
20 MINUTES TO KEY WEST , BOATERS PARADISE
Exterior

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (57)
"Great place to stay. We will be back. Eric is very responsive, and we had a great experience staying at his property in Venture Out. "
20 MINUTES TO KEY WEST , BOATERS PARADISE
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Exterior

Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

9.6 out of 10, Exceptional, (51)
"Great location & great boating access."
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi
A heated pool

Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi

8.4 out of 10, Very Good, (22)
"We loved the location and being on water"
Canal-front home w/dock, resort-style amenities, patio, & high-speed WiFi
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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