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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Lower Keys Vacation Homes

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Pool

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Enjoy cooking and dining in this well-equipped kitchen with a central island, oven, and ample counter space.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

9.0 out of 10, Wonderful, (151)
"The place was spacious, very clean and beautiful!"
The price is CA $380
CA $833 total
includes taxes & fees
Aug 3 - Aug 4
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Old Florida Style, wrap around porch, boat basin for dockage, open water
Relax on the waterfront with Adirondack chairs and a small dining table.

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"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
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Enjoy ocean views from the spacious balcony and covered porch of this coastal retreat.

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

9.8 out of 10, Exceptional, (250)
"Home was clean and great location! Would definitely stay here again! "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Enjoy a serene beach experience with a clear ocean view, lounge chairs, and a dock for water activities.

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.8 out of 10, Excellent, (85)
"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. "
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Enjoy cooking in this well-equipped kitchen with a central island and standard appliances.

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

9.6 out of 10, Exceptional, (56)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift
Boats dock at the marina, offering a serene waterfront view.

Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift

9.4 out of 10, Exceptional, (8)
"We had a wonderful holiday vacation. Thank you Kelly and Walter for sharing your vacation rental with our family."
Big Pine Key Unique Direct Ocean Access with 10K lbs private dock boat lift
20 MINUTES TO KEY WEST , BOATERS PARADISE
Enjoy waterfront views and access to a marina from this coastal property.

20 MINUTES TO KEY WEST , BOATERS PARADISE

9.4 out of 10, Exceptional, (57)
"Comfortable and very well appointed! High end amenities, and very responsive host ensured our stay was a memorable one. Our third time booking this property and can’t think of anything they could improve!"
20 MINUTES TO KEY WEST , BOATERS PARADISE
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)
"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."
Private Secluded Ocean View & Pool Near Key West
A Tropical Luxury Getaway, Your own private resort!!
Relax by the serene pool surrounded by lush palm trees.

A Tropical Luxury Getaway, Your own private resort!!

10.0 out of 10, Exceptional, (38)
"The house and pool were very nice."
A Tropical Luxury Getaway, Your own private resort!!
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Relax by the pool surrounded by palm trees and a sandy deck.

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.2 out of 10, Wonderful, (7)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is CA $365
CA $853 total
includes taxes & fees
Aug 18 - Aug 19
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Relax by the beachside with picnic tables nestled among tall palm trees.

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.6 out of 10, Exceptional, (40)
"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!
Island Time #110 Ocean Views - Cudjoe Key
Relax by the pool surrounded by palm trees and lounge chairs, with a clear view of the sea.

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.8 out of 10, Exceptional, (6)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
The price is CA $365
CA $853 total
includes taxes & fees
Aug 19 - Aug 20
Island Time #110 Ocean Views - Cudjoe Key
Lower Keys paradise
Relax by the oceanfront pool surrounded by lounge chairs and palm trees.

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
Newly renovated cozy and spacious beach house with breathtaking ocean front
Enjoy waterfront views from the dock, where a small boat is moored and a covered seating area invites relaxation.

Newly renovated cozy and spacious beach house with breathtaking ocean front

10.0 out of 10, Exceptional, (11)
"I stayed at this property with my brother and mom. We all loved this house. Several key deer and an iguana frequented the property. Great location and close to everything we wanted to do. We were all sad to see that it’s not available to stay at again next year. "
Newly renovated cozy and spacious beach house with breathtaking ocean front
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View
Enjoy waterfront views from this serene outdoor space with a seating area, staircase, and beautiful pelican sculpture.

VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View

9.8 out of 10, Exceptional, (71)
"Very pleased with this adorable home thank you "
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Enjoy a serene beachside setting with picnic tables arranged around a central rock mound, surrounded by palm trees and a stunning ocean view.

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (96)
"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 CA $205
CA $601 total
includes taxes & fees
Aug 11 - Aug 12
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Enjoy waterfront views from the covered outdoor area and balcony of this two-story property.

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

9.6 out of 10, Exceptional, (52)
"Great location & great boating access."
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
Keys House - Venture Out Lot 220
Enjoy a peaceful ocean view from this serene balcony with a palm tree in the background.

Keys House - Venture Out Lot 220

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the condo and spent a lot of time on the upper patio enjoying the view. Very clean. Spacious for 4 of us. Felt extremely safe. Thank you very much!!!"
Keys House - Venture Out Lot 220
Tarpon Alley - Venture Out 509
Enjoy a scenic view from the two-story house's prominent balcony and covered porch area, adjacent to a body of water.

Tarpon Alley - Venture Out 509

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very clean , very well equipped. Very nice home. Very comfortable inside and out. Wish I was still there ! Would absolutely recommend. "
Tarpon Alley - Venture Out 509
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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Top Lower Keys Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Loved the property and all of the free activities! We definitely took advantage of the kayaks, paddle boards, pool and hammocks. "
Jessica 2-night trip
Posted 1 day ago
Parmer's Resort