Search Vacation Homes in Big Pine Key

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Compare Vacation Homes in Big Pine Key with updated reviews, rates, and availability.

Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, 104 reviews
"Right on the water. Very neat place. "
The price is $145
$304 total
includes taxes & fees
Jun 4 - Jun 5
Aqua Lodge Rentals At Coconut Cay
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
10.0 out of 10, Exceptional, 201 reviews
"This is our second time here and will not be our last. Love the set up of the house, the screened in porch, the pool of course, basically love everything. Know you will enjoy your time as well."
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
Sombrero Beach 4bed 2 bath Pool Tiki Bar & 50 ft for Docking & Steps to Beach
10.0 out of 10, Exceptional, 6 reviews
"My family had a wonderful time!"
Sombrero Beach 4bed 2 bath Pool Tiki Bar & 50 ft for Docking & Steps to Beach
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Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very Good, 90 reviews
"Explain to people that there is an opportunity to park the truck with a trailer and that there are ramps for the boat because I myself did not take my boat thinking that there was nothing like that. Thanks "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
NEW LISTING DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
NEW LISTING DISCOUNT! Beautiful Home, Dock, Cabana Club Membership, Pool, Beach!
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, 47 reviews
"So glad we found this location. Nice and peaceful but close to anything we needed. Sitting on the porch was so relaxing, watching boats go by. The house was very comfortable. Only wish the 2nd bedroom had a working TV. Our host was quick to answer any issue we had and left some great suggestions on places to eat. I would definitely return to enjoy this beautiful location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
9.6 out of 10, Exceptional, 71 reviews
"Wonderful little place to stay"
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Keys Elegant House Single Family. Private Pool, Hot Tub, Dock. Summer Specials
9.6 out of 10, Exceptional, 46 reviews
"We stayed for a week in May! The location was great! The house had pretty much everything we needed. The beds were comfy. The pool was awesome! We paid for the heat in the hot tub but didn’t need it! Lots of seating outside. The ceiling fans on the lanai were great! They had so many towels! They do require you wash towels (that aren’t part of everyday use in the bathroom) but that was no big deal with the stackable washer and dryer in the house."
Keys Elegant House Single Family. Private Pool, Hot Tub, Dock. Summer Specials
FL Keys - Marathon, FL - 3bd and 4ba - salt water pool - boat dock - sleeps 8
10.0 out of 10, Exceptional, 1 review
"We had an amazing time. I have been renting vacation homes for 30 years and this home is one of our favorites. Jerry does a great job communicating with you from the very first message and throughout your stay. He handles any issues immediately. The layout of the home gives everyone privacy and space. The view is fabulous. The pool is incredible. The pool house is fun to hang out in and has a beauful view. The kitchen is well stocked and the ice maker was a fabulous bonus! Fishing poles were fun...
FL Keys - Marathon, FL - 3bd and 4ba - salt water pool - boat dock - sleeps 8
VR13 Salt-Water-Revival -North | 3 Bed, 2 Bath
9.8 out of 10, Exceptional, 17 reviews
"Fun trip"
VR13 Salt-Water-Revival -North | 3 Bed, 2 Bath
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, 186 reviews
"All amenities were operational and organized. check in/check out process was easy. i thoroughly enjoyed my stay with friends. thanks"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Waterfront - 5 BR, 4 Full Bath, Pool, 80' Dock, Ample Parking, Tiki Hut, Jacuzzi
10.0 out of 10, Exceptional, 23 reviews
"Nice spot! Would highly recommend."
Waterfront - 5 BR, 4 Full Bath, Pool, 80' Dock, Ample Parking, Tiki Hut, Jacuzzi
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
9.2 out of 10, Wonderful, 90 reviews
"Location and outdoor living space was awesome!"
OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
Boot Key Harbour Deep Water Canal Home, Walk to Tiki Bars, Restaurants and More!
10.0 out of 10, Exceptional, 60 reviews
"We would recommend this property to everyone. Was clean, beautiful. Great location. Close to everything. Property was perfect never had to leave if you wouldn't want to. Had everything. Can't say enough good to things. You will not be disappointed."
Boot Key Harbour Deep Water Canal Home, Walk to Tiki Bars, Restaurants and More!
welcome to Luna Island in the Florida Keys
10.0 out of 10, Exceptional, 21 reviews
"Very pleased with the location and the accommodations. Our host was quick to respond any time we reached out to her. Loved the pool, great kitchen for cooking and family time. Best of all was just a short walk to the beach."
welcome to Luna Island in the Florida Keys
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
9.6 out of 10, Exceptional, 13 reviews
"What a beautiful home. Great views of the ocean and the sunrises were amazing. Neighbors were awesome and fun to talk to. just an incredible place."
LICENSE TO CHILL ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cozy, Perfect Conch Cottage!
9.0 out of 10, Wonderful, 30 reviews
"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!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, 217 reviews
"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
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, 73 reviews
"We always enjoy staying at venture out. They have everything you need right on the premises. Janet’s house was perfect for myself and three kids. Right on the canal so the kids could fish and even had a manatee come right up to us. We will definitely be back."
The price is $179
$475 total
includes taxes & fees
Jun 3 - Jun 4
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
9.8 out of 10, Exceptional, 100 reviews
"We had the best time staying at this beautiful property! The kids loved swimming in the pool and watching the manatee off the dock. My husband and I enjoyed sitting on the dock drinking our coffee and closing out the day with a glass of wine. The new black stone made it super easy to cook our fresh caught fish. My kids said the only issue is they wanted to stay longer. Cannot wait to go back! Thank you Divina!"
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Don't see what you're looking for?
See all available properties in Big Pine 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 Big Pine Key

Old Wooden Bridge Resort and Marina
2.5 star property
8.6 out of 10, Excellent, 127 reviews
"Family trip. We loved this hidden gem in Big Pine Key. The cabins on land are beautiful, spacious and confortable. The pictures don’t make them justice. New and well equipped. You’ll be surrounded by nature with frequent encounters with Key Deer. They add uniqueness to the quiet ambience. Key West is about 40 min away. I highly recommend Old Wooden Bridge! "
The price is $139
$256 total
includes taxes & fees
Jun 2 - Jun 3
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, 130 reviews
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Keys 3 Bedroom Corner Home near Beach & Key West
9.4 out of 10, Exceptional, 3 reviews
"Absolutely lovely property. The only thing we regretted was not having more time to spend there. We loved the nearby restaurant called “The Boardwalk Pub & Grill. They have a very friendly staff and they’re very accommodating in the changes they make to their menu."
The price is $359
$797 total
includes taxes & fees
Jun 25 - Jun 26
Keys 3 Bedroom Corner Home near Beach & 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.

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