Search Vacation Homes in Big Pine Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Big Pine Key holiday homes

Keys 3 Bedroom Corner Home near Beach & Key West

Keys 3 Bedroom Corner Home near Beach & Key West
Sands
9.4 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Patricia H.
The price is HK$2,578
HK$5,970 total
includes taxes & fees
5 May - 6 May
Keys 3 Bedroom Corner Home near Beach & Key West

Florida Keys vacation home, Family sized and pet friendly home with a pool!

Florida Keys vacation home, Family sized and pet friendly home with a pool!
Key Colony Beach
10.0 out of 10, Exceptional, (28 reviews)
"It felt very homey and comfortable! Gorgeous view. "
United States
Samantha S.
Florida Keys vacation home, Family sized and pet friendly home with a pool!

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY
Marathon
9.8 out of 10, Exceptional, (63 reviews)
"This was our second time staying in this house lots of room great location."
United States
Anonymous traveller
The price is HK$2,335
HK$7,763 total
includes taxes & fees
30 May - 31 May
SOMBRERO BEACH LARGE 4/3 HOME w/ HEATED POOL, 40 ft BOAT DOCK, BEACH NEARBY

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

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (105 reviews)
"Wonderful family getaway"
United States
Anthony V.
The price is HK$3,134
HK$6,458 total
includes taxes & fees
3 Jun - 4 Jun
Old Florida Style, wrap around porch, boat basin for dockage, open water

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"Great location and Host was very helpful and responsive."
United States
Dennis G.
Kelly's Kabin - Adorable Private Summerland Key Cottage

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (107 reviews)
"Janet and Jerry were excellent hosts and the property was perfect for our trip "
United States
Shayne H.
The price is HK$1,089
HK$3,281 total
includes taxes & fees
5 May - 6 May
SAVE BIG $$$ APRIL! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is HK$1,481
HK$4,635 total
includes taxes & fees
5 May - 6 May
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

One of the very few beach houses with a daily, rental license in the Keys.

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (68 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is HK$3,910
HK$10,161 total
includes taxes & fees
17 May - 18 May
One of the very few beach houses with a daily, rental license in the Keys.

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Cudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is HK$1,769
HK$5,022 total
includes taxes & fees
10 May - 11 May
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (87 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is HK$1,951
HK$4,407 total
includes taxes & fees
12 May - 13 May
SAVE BIG $$$ APRIL! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
8.0 out of 10, Very good, (17 reviews)
"Good experience. The property is well place and the Venture is really nice and quiet."
United States
Primeau J.
The price is HK$1,530
HK$3,523 total
includes taxes & fees
11 May - 12 May
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is HK$1,563
HK$4,736 total
includes taxes & fees
7 May - 8 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
Island Time #110 Ocean Views - Cudjoe Key

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is HK$2,057
HK$5,377 total
includes taxes & fees
17 May - 18 May
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (24 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is HK$2,742
HK$5,300 total
includes taxes & fees
25 May - 26 May
Spanish Queen @Venture Out, Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is HK$1,920
HK$5,163 total
includes taxes & fees
31 May - 1 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
Cudjoe Key
8.0 out of 10, Very good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is HK$1,522
HK$4,682 total
includes taxes & fees
5 May - 6 May
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is HK$2,262
HK$5,609 total
includes taxes & fees
22 May - 23 May
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Big Pine Key Hotel Reviews

Find out more about Big Pine Key

Big Pine Key Vacation Homes information

Number of reviews
531
Accommodation
1655 Vacation Homes
Lowest Price
HK$3,281
Highest Price
HK$10,161

Explore a world of travel with Expedia