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Compare 1675 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, (147)
"Great property with gorgeous view of the water. Lovely little house boat for a family of four. Everything that you need for an amazing stay. Grounds were clean and quiet. Saltwater pool was fantastic. Nothing fancy but great vacation. Would stay again."
The price is SAR 821
SAR 1,485 total
includes taxes & fees
8 Apr - 9 Apr
Aqua Lodge Rentals At Coconut Cay

Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

10.0 out of 10, Exceptional, (83)
"Beautiful outdoor patio, amazing pool, and a very well air conditioned house. We had a great week here, only thing we wished was different was the jacuzzi connected to the pool was the same temperature as the pool, other than that, fantastic host and property. "
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!

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

8.8 out of 10, Excellent, (140)
"We fell in love with this property upon our arrival and during our stay! It was very comfortable and the large screened in porch with a view of the Atlantic was one of the stars of our stay during breakfast sipping coffee in the morning and cocktails in the evening. We enjoyed the peacefulness while we relaxed at the pool. We had two minor issues and after contacting the property manager they were fixed within the hour. We definitely would stay here again."
The price is SAR 1,125
SAR 2,343 total
includes taxes & fees
25 Apr - 26 Apr
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (134)
"My sister and friend from north Alabama and my youngest daughter and I decided on a last minute mini vacation. We found this little gem of a place while looking for places to stay in the Keys. Although it could use some TLC, we found the property to be clean, well-stocked and perfect for a short stay, some family time, rest and relaxation. We truly enjoyed our stay and would definitely consider staying here again,"
The price is SAR 1,032
SAR 2,260 total
includes taxes & fees
2 Apr - 3 Apr
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

9.8 out of 10, Exceptional, (91)
"The host was extremely responsive to any requests that we had. We loved the stay, great location. The house met all of our needs. Walkable area to some things. The host was very helpful and accommodating, would definitely recommend. "
Coral Lagoon Single Family Home 3bed/2.5bath with 40' Boat Slip w/ Power + Water

COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

10.0 out of 10, Exceptional, (34)
"Everything in the listing was completely accurate. Halfway point in the Keys. The home was very clean. Air Conditioning was spot on. We used the pool/hottub a lot. Surprised how much we used the hot tub as almost every day it was clear and hot. Although it didn’t bother us, the home is located in the direct path of a variety of planes jets and helicopters landing at Airport nearby. Noise was quite loud and may scare some dogs. Our Morkie had no issues. Definitely would rent property...
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property

2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

9.6 out of 10, Exceptional, (118)
"My family (10 of us all together) stayed at this beautiful property and could not have been more pleased! It was spacious enough for all of us and close to all the things we wanted to do! Beth was super responsive anytime we reached out to her! The only thing I would note is that the house is in the DIRECT landing path for the airport down the road. It was a little startling when some of the jets were flying in. This is nothing against the house itself, just something to be aware of.We hope to...
2499 Rental Rate ANY WEEK March-Aug 2025 fees and taxes add, except holidays

VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

9.6 out of 10, Exceptional, (46)
"Overall it was good. They could use more cooking bowls and sharper knives"
VR65 Beach Nuts | 4 Bed, 2 Bath Next to Sombrero Beach

Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

9.6 out of 10, Exceptional, (65)
"Nice property with good amenities-especially for young children. Some things were not as advertised. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool

🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!

10.0 out of 10, Exceptional, (45)
"Great week in the Keys! This property has amazing outdoor space! Great fishing off the dock, easy access to Sisters Creek and the Atlantic. The pool area is perfect and well kept. Very quiet and private neighborhood and close to everything, restaurants, grocery store, and beach. The house is well equipped and has COLD A/C, it is a bit dated but suited our family and friends just fine. We are outside people and just need a place to shower and recoup for the next day.. We would definitely stay...
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (5)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is SAR 1,234
SAR 2,842 total
includes taxes & fees
6 Apr - 7 Apr
Keys 3 Bedroom Corner Home near Beach & Key West

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (87)
"Nice property. We enjoyed our stay."
Private Secluded Ocean View & Pool Near Key West

Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

10.0 out of 10, Exceptional, (251)
"Highly recommend staying at this condo. "
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut

Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244

9.8 out of 10, Exceptional, (15)
"This place was nice and had some updates. The biggest thing for us is cleanliness. The housekeeper on the property needs to do a thorough job vacuuming and a least wash the floor every now and then. There were LONG dark hairs all over the place. That’s what prompted us to vacuum and the floor “looked” clean but was dirty. We washed the area we were using. We only used the main bedroom and the bed was very comfortable. The bathroom had been updated in recent years and was very roomy. The...
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244

Home in Marathon w/ boat lift

Home in Marathon w/ boat lift

Luxury Waterfront Oasis w Heated Pool and 50' Dock

10.0 out of 10, Exceptional, (26)
"Our family had an absolutely wonderful stay at this fantastic property! From the moment we arrived, we were impressed by how clean, spacious, and well-equipped the home was. It was the perfect size for our group, with plenty of room for the kids to play and the adults to relax. The kitchen had everything we needed to cook meals together, which was a huge plus for our family. The beds were super comfortable, and the living areas were cozy and inviting—perfect for our movie nights. The outdoor...
Luxury Waterfront Oasis w Heated Pool and 50' Dock

KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

9.4 out of 10, Exceptional, (78)
"The property was very nice and well maintained. The location was good. A couple lawn chairs for the patio/dock would be great."
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts

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

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

Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water

10.0 out of 10, Exceptional, (146)
"Pool and hot tube was great Househad everything you need for a long stay "
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water

Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!

10.0 out of 10, Exceptional, (70)
"We had a wonderful time during our stay in the Florida Keys! The home and adjacent canal lot were spacious, comfortable, and very inviting. We completely recommend staying at Kathy's property!"
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
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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Other property types in Big Pine Key

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (204)
"Great place to stay !! Especially if you like this type of thing !! Fishing is awesome and very close to the bridge spent many many hours out there !!"
The price is SAR 521
SAR 962 total
includes taxes & fees
31 Mar - 1 Apr
Old Wooden Bridge Resort and Marina

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (145)
"We enjoyed the stay so much. Great pool area and very friendly staff!!"
Sunshine Key RV Resort & Marina

Keys 3 Bedroom Corner Home near Beach & Key West

9.6 out of 10, Exceptional, (5)
"We stayed for four nights. They have ample beds, a nice tv, a large kitchen, and many parking spots. There are not many walkable beaches but there is a couple of good restaurants nearby. We had a great time, everything was nice, and everything was as listed. I would rent again. "
The price is SAR 1,234
SAR 2,842 total
includes taxes & fees
6 Apr - 7 Apr
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.