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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 1675 Vacation Homes in Big Pine Key with updated reviews, rates, and availability.

Aqua Lodge Rentals At Coconut Cay
Front of property

Aqua Lodge Rentals At Coconut Cay

3.5 star property
9.6 out of 10, Exceptional, (161)
"Truly enjoyed our time in such a unique experience. "
The price is AED 592
AED 1,191 total
includes taxes & fees
13 May - 14 May
Aqua Lodge Rentals At Coconut Cay
Dragonfly Lite – A tropical oasis with your own heated saltwater pool to enjoy!
Terrace/patio

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

10.0 out of 10, Exceptional, (88)
"This was a much needed break! Dragon fly lite was absolutely perfect in every way. Jerry and Barbie were great at communicating. I enjoyed the peaceful vibe, the pool area is incredible!"
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
Fridge, microwave, oven, stovetop

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

8.8 out of 10, Excellent, (146)
"Good location "
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

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

8.8 out of 10, Excellent, (139)
"Great location and house was clean. "
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
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (94)
"The place is EXACTLY as advertised. Host was immediately responsive. The place was VERY clean, and comfortable! Convenient location for anything you want to do in the Keys. Walking distance to a couple of good restaurants - we highly recommend Island Fish Company! The pool was lovely and relaxing. I would highly recommend staying here. Thanks for the memories!"
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
Terrace/patio

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

10.0 out of 10, Exceptional, (35)
"The house was clean, owner was great at responding and we all just really loved the house. It also was a lot more spacious than we were expecting inside, and the backyard was huge just like the photos showed. Great place to stay! "
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!
Outdoor pool, a heated pool

LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!

9.6 out of 10, Exceptional, (120)
"Enjoyed our time in Marathon, the property was very nice. We only needed 4 of the bedrooms and did not use the bunk bed room which is great as the room is directly off the master suite. If we had small children "
LAST MINUTE SPECIAL! May 10-17th 1950 + the fees!!!
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
Outdoor pool, a heated pool

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

9.6 out of 10, Exceptional, (68)
"Property was great for our group. 2 miles to grocery stores. Pool was great! Used the bikes and had a great time here. "
Spacious Waterfront Home on a Direct Ocean Access Canal with a Chilled Pool
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!
Aerial view

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

10.0 out of 10, Exceptional, (45)
"Very easy to get to and good parking for vehicles and trailer"
🌴Beach, Pool, Dock,Boating, and Golfing Paradise!!🌴Pets Welcomed!
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (90)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West
Coral Lagoon #13: Pool, Water Views, Both Gulf & Atlantic Access via Vaca Cut
Beach towels

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

10.0 out of 10, Exceptional, (254)
"We enjoyed the location of the home. We could walk to a some bars/restaurants which is always a plus. The home was very clean and comfortable. The hosts were always very responsive when we had questions - thanks."
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
Smart TV

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

9.8 out of 10, Exceptional, (19)
"We had a wonderful stay at the house while we explored the Keys. Unfortunately the weather was cold, but it was nice to retreat in the evenings back at the house. The house is clean, well-stocked (we could’ve used more towels), the primary bedroom is super comfy with a great shower, and the location of the house on the water is lovely! Highly recommend!"
Bikini Bottom - 3 Bedroom Home Canal With Boat Lift - Rental Lic# VACA-23-244
Luxury Waterfront Oasis w Heated Pool and 50' Dock
On the beach, beach towels

Luxury Waterfront Oasis w Heated Pool and 50' Dock

9.8 out of 10, Exceptional, (29)
"This house is paradise. From the heated pool to the outdoor bar area. I highly recommend this gem..."
Luxury Waterfront Oasis w Heated Pool and 50' Dock
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
On the beach

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

9.4 out of 10, Exceptional, (79)
"The place is good to stay very quiet near to the cabana club very nice people "
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!
Shower, hair dryer, towels

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

10.0 out of 10, Exceptional, (1)
"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!
Open Water views, 100' dock Private Pool Ice machine DIRECT ACCESS open water
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (149)
"Wonderful place to 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!!
Terrace/patio

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

10.0 out of 10, Exceptional, (73)
"The house was very clean and the fishing was fun for me and the kids! We caught fish everyday!Lots of nice restaurants in Marathon as well.Thank you for the great memories!!"
Don't Miss This! Deep Water Canal, Swimspa Pool, Kayaks, Walk to Tiki Bars!!
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
Outdoor pool, a heated pool

Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock

10.0 out of 10, Exceptional, (17)
"Wondeful home for our trip to Marathon! Everything was as advertised. Best stocked VRBO we have stayed in. Outdoor kitchen and pool area were awesome! Would definitely recommend!!"
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14
Aerial view

Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14

10.0 out of 10, Exceptional, (2)
"Great property, modern, plenty of room, movie room was great, AC perfect, kitchen well equipped, linens were high quality, all outdoor amenities, bikes, paddle boards, putting green, hammocks were awesome, great filtered water, convenient to resteraunts, dock and boating were fantastic. best property in Marathon."
Paradise Oceanside Estate- 6 Bedrooms & 9 BR + Office + Theater Room – SLEEPS 14
Large Full Duplex with Pool / Hot tub Pet Friendly 581- 591 10th Street
Outdoor pool, a heated pool

Large Full Duplex with Pool / Hot tub Pet Friendly 581- 591 10th Street

10.0 out of 10, Exceptional, (10)
"We had a great time at this property. The photos don’t do it justice, it’s a lot nicer than what I expected. It was so great to have our boat, a hot tub and pool as well. Lots of parking for everyone as well. "
Large Full Duplex with Pool / Hot tub Pet Friendly 581- 591 10th Street
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 Bedroom Aqua Lodge # 13 Barracuda | Living area | Flat-screen TV

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (234)
"price - clean and newly renovated boats - nice staff - easy check in/out."
The price is AED 511
AED 942 total
includes taxes & fees
12 May - 13 May
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
Kayaking

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (146)
"We enjoyed the stay so much. Great pool area and very friendly staff!!"
Sunshine Key RV Resort & Marina
Tropical Caribbean Paradise with pool!
Pool

Tropical Caribbean Paradise with pool!

9.2 out of 10, Wonderful, (86)
"It was a place to sleep. Camper is old and needs work. Was fairly clean. "
Tropical Caribbean Paradise with pool!
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.