Search Vacation Homes in Big Pine Key

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Big Pine Key

The Hammocks at Marathon
Outdoor pool, pool umbrellas, sun loungers

The Hammocks at Marathon

2.5 star property
9.0 out of 10, Wonderful, (98)
"We loved the location of the property and we also loved the entertainment/singer provided by lounge."
The Hammocks at Marathon
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
Outdoor pool, a heated pool

FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays

9.6 out of 10, Exceptional, (121)
"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 "
FALL SPECIAL 40% off Rental Rate! Sep-Dec 2025 except holidays
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, (80)
"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
WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656
Interior

WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656

10.0 out of 10, Exceptional, (151)
"Beautiful property! Can't say enough about it. Just like the pictures. Lots of extras....laundry soap, beach chairs, small cooler, beach towels, plenty of bath towels, every kitchen utensil, even spices. On demand hot water, large permanent umbrella above the table near the pool (different than the pictures) Home is in excellent condition. We plan to return. "
WOW! PRIVATE POOL, OCEAN FRONT, & DOCK Sister house next-door VRBO#1034656
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, (97)
"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
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks
Outdoor dining

Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks

10.0 out of 10, Exceptional, (90)
"Great location. Great view. This place has it all. "
Oceanfront, Pool, Tiki Hut, Magnificent Views, Near Vaca, Great Dockage, Kayaks
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, (52)
"It was a beautiful home and Francine, our host, was most accommodating."
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Terrace/patio

Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.

10.0 out of 10, Exceptional, (8)
"Comfortable place in a nice neighborhood with a beautiful view"
Charming 55' Waterfront Paradise, Fishers Dream, Bring Your Boat & Enjoy.
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW
Sun loungers, beach towels

Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW

10.0 out of 10, Exceptional, (129)
"Super cute and clean cottage, well appointed and centrally located. "
Private Waterfront Single Family Home,Heated Pool,Dock,Ocean Views,Kayaks, WOW
Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access!
Outdoor dining

Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access!

Waterfront Paradise in Marathon Key – 3BR Home with Private Canal Access!
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, (222)
"We loved our stay here! This place had everything that we needed. The resort was safe for my kids to roam around for pickleball, swimming, and fishing. Thank you!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Summer Openings Including Mini Season! Deep Water Canal, SwimSpa Pool, Kayaks!
Aerial view

Summer Openings Including Mini Season! Deep Water Canal, SwimSpa Pool, Kayaks!

10.0 out of 10, Exceptional, (155)
"The house was very nice. A quiet retreat for the week. We even had a chance to see a manatee in the canal. "
Summer Openings Including Mini Season! Deep Water Canal, SwimSpa Pool, Kayaks!
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
Property grounds

Key Colony Home with Dock and Cabana Club Access- Pets Welcomed

10.0 out of 10, Exceptional, (14)
"Nice home , would book again "
Key Colony Home with Dock and Cabana Club Access- Pets Welcomed
Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak
Outdoor dining

Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak

9.6 out of 10, Exceptional, (87)
"Fantastic house and property ! Location, pool and Cleanliness were all superb. Will definitely book here again !"
Amazing 4 BR/2BA home, Pool/Hot Tub, Oceanside canal, Kayak
Waterfront Key Colony Beach Home w/ Golf Cart!
Pool

Waterfront Key Colony Beach Home w/ Golf Cart!

2.0 star property
9.6 out of 10, Exceptional, (4)
"We really enjoyed the location, the local beach & pool club, everything was walkable or we could use the golf cart. Condo was clean, comfortable and had everything we needed. Friendly and responsive property manager, thanks so much! "
Waterfront Key Colony Beach Home w/ Golf Cart!
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
Outdoor pool, a heated pool

"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage

10.0 out of 10, Exceptional, (222)
"Quick responses from the host. Great location and home has lots to offer!"
"Your own private resort" - Mockingbird Pointe - Waterfront, pool and dockage
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

8.6 out of 10, Excellent, (82)
"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
Fandango - private pool
Pool

Fandango - private pool

9.8 out of 10, Exceptional, (78)
"My family and I had a great time staying at Fandago. It was located close enough to Key West to visit, yet far enough away to enjoy some privacy and peace and quiet. We were there for my daughter's wedding and everything was absolutely perfect! Would definitely stay again!"
Fandango - private 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!
LAST MIN OPENING~6/7-14, 2025 Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~
Outdoor pool, a heated pool

LAST MIN OPENING~6/7-14, 2025 Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~

10.0 out of 10, Exceptional, (37)
"Great experience. Would definitely rent again!"
LAST MIN OPENING~6/7-14, 2025 Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free