The 10 best vacation homes in Big Pine Key, US | Booking.com
Skip to main content

The best vacation homes in Big Pine Key

Check out our selection of great vacation homes in Big Pine Key

Filter by:

Review score

Island Oasis ~ YOUR Paradise Awaits!

Cudjoe Key (Near Big Pine Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodations with access to a hot tub. Guests may go for a swim in the private pool.

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 6 reviews
Price from
$335.70
1 night, 2 adults

Sugarloaf Key RV Resort & Cottages

Summerland Key (Near Big Pine Key)

Sugarloaf Key RV Resort & Cottages provides air-conditioned accommodations in Summerland Key. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

R
Roseanne
From
United States
I love the cute perfect size comfy cottages! So clean and the bed was so comfy. The living room area was perfect to relax in. The shower was a great size and clean! The staff was nice! Can not wait to plan our next trip.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 312 reviews

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key (Near Big Pine Key)

Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

B
Bettinna
From
United States
Location, attention to detail, and soooo many amenities!
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 20 reviews

NAUTILUS...ocean front cottage retreat ~

Cudjoe Key (Near Big Pine Key)

Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.

A
Anonymous
From
United States
Everyone was super friendly at the resort and it was an easy check in
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews

OCEANIA... water front cottage retreat ~

Cudjoe Key (Near Big Pine Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodations with access to a sauna and hot tub.

A
Anonymous
From
Curaçao
Love this place, was nice and quiet and had all the comforts we wanted. Dishwasher, washing and drying machines, good beds, badrooms a little on the small side but it even so was ok. We were close to Key West and also Marathon, both about 30 minutes drive. We did make us of the kayaks and our son went fishing alot. Will book this again next time we go to the keys.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews

Tree Top Paradise

Cudjoe Key (Near Big Pine Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tree Top Paradise provides accommodations with access to a spa center.

V
Vernon
From
United States
The scenery was beautiful the area was in good location and it also have their own store in the area which is a plus. The store has bait shop and gas for your boat. I surely would book again
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 30 reviews

Dock Holiday

Cudjoe Key (Near Big Pine Key)

Dock Holiday offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street. The vacation home has access to a restaurant.

M
Mary
From
United States
Wonderful location. Exceptionally clean. Fully stocked. Peaceful community. Just all around an A+!
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 6 reviews

PARADISE AT SUNSET

Marathon (Near Big Pine Key)

Featuring free bikes, PARADISE AT SUNSET provides accommodations in Marathon. This property offers a private pool, free Wifi, and free private parking.

C
Carolyn
From
United States
Location was great. The house had plenty of room for everyone.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 6 reviews
All vacation homes in Big Pine Key

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Big Pine Key and surrounding area in the past month

See all

Enjoy breakfast in Big Pine Key and nearby

  • Sunset Villa

    Big Pine Key
    Breakfast options

    Sunset Villa offers accommodations in Big Pine Key, 24 miles from Florida Keys Aquarium Encounters and 18 miles from Seven Mile Bridge. The vacation home has access to a restaurant.

  • Big Pine Key Dreams offers accommodations in Big Pine Key, 25 miles from Florida Keys Aquarium Encounters and 19 miles from Seven Mile Bridge. The vacation home has access to a restaurant.

  • Salty Air Retreat offers accommodations in Little Torch Key, 26 miles from Florida Keys Aquarium Encounters and 29 miles from Ernest Hemingway Home and Museum.

  • Cayo Loco

    Little Torch Key
    Breakfast options

    Cayo Loco is located in Little Torch Key, just 25 miles from Florida Keys Aquarium Encounters and 29 miles from Ernest Hemingway Home and Museum. The vacation home has access to a restaurant.

  • Foster`s Folly

    Key West
    Breakfast options

    Foster`s Folly is located in Key West, just 30 miles from Duval Street and 30 miles from Southernmost Point. The air-conditioned accommodation is 30 miles from Ernest Hemingway Home and Museum.

  • L`archipel

    Key West
    Breakfast options

    L`archipel is located in Key West, just 27 miles from Duval Street and 28 miles from Southernmost Point. The air-conditioned accommodation is 27 miles from Ernest Hemingway Home and Museum.

  • Experience Coastal Living at its Best Florida Keys is located in Summerland Key, just 26 miles from Florida Keys Aquarium Encounters and 27 miles from Ernest Hemingway Home and Museum.

  • Villa Lucie

    Summerland Key
    Breakfast options

    Villa Lucie offers accommodations in Summerland Key, 28 miles from Duval Street and 28 miles from Southernmost Point.

Save money on vacation homes in Big Pine Key and nearby – budget options available

  • Cayman Cottage

    Summerland Key
    Budget options available

    Cayman Cottage offers accommodations in Summerland Key, 28 miles from Duval Street and 28 miles from Southernmost Point.

  • Tradewinds Treat

    Big Pine Key
    Budget options available

    Tradewinds Treat offers accommodations in Big Pine Key, 27 miles from Florida Keys Aquarium Encounters and 17 miles from Seven Mile Bridge. Guests can benefit from a balcony and an outdoor fireplace.

  • Skyway Living

    Summerland Key
    Budget options available

    Skyway Living offers accommodations in Summerland Key, 25 miles from Ernest Hemingway Home and Museum and 25 miles from Duval Street.

  • Summerland Canal

    Summerland Key
    Budget options available

    Summerland Canal is located in Summerland Key, just 25 miles from Ernest Hemingway Home and Museum and 25 miles from Duval Street.

gogless