Big Pine Key Vacation Rentals

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Our top choices for Big Pine Key vacation rentals

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (336 reviews)
"I love the place, for the next time I will stay for more days "
United States
Kenia
The price is CA $159
CA $371 total
includes taxes & fees
May 31 - Jun 1
Old Wooden Bridge Resort and Marina

🌴 TROPICAL RETREAT 🌴 RV in the Keys

🌴 TROPICAL RETREAT 🌴 RV in the Keys
Big Pine Key
9.4 out of 10, Exceptional, (6 reviews)
"Had a great time. The owner was very communicative through the whole process. Camper had everything thing we could have needed. We really enjoyed our stay and if we ever decide to go to the keys again, we will definitely book with Heather and her camper. "
United States
Lorie W.
The price is CA $183
CA $448 total
includes taxes & fees
May 12 - May 13
🌴 TROPICAL RETREAT 🌴 RV in the Keys

Charming 3-bedroom house in Big Pine Key near Beach and Key West

Charming 3-bedroom house in Big Pine Key near Beach and Key West
Sands
8.0 out of 10, Very good, (10 reviews)
"Great property, surrounded by key deer and wild roosters. "
United States
Scott B.
The price is CA $245
CA $758 total
includes taxes & fees
May 12 - May 13
Charming 3-bedroom house in Big Pine Key near Beach and Key West

Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is CA $409
CA $615 total
includes taxes & fees
May 12 - May 13
Beach View Room Dormitory Room Barnacle Resort

Star Room Barnacle Resort

Star Room Barnacle Resort
Long Beach Estates
8.8 out of 10, Excellent, (5 reviews)
"We loved the location - quiet and secluded - away from everything but not so far away that you felt isolated. All very clean and amenities were as described."
United Kingdom
Robert
The price is CA $310
CA $461 total
includes taxes & fees
Jun 2 - Jun 3
Star Room Barnacle Resort

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴
Big Pine Key
8.8 out of 10, Excellent, (3 reviews)
"Host was very responsive! Camper was clean and in good location. Table bed was very hard and didn’t sleep great, however it was a very good size bed. We would stay again."
United States
Pearl A.
The price is CA $122
CA $372 total
includes taxes & fees
May 25 - May 26
🌴 TROPICAL RETREAT 🌴 RV IN THE KEYS 🌴

Treehouse Private Village Barnacle Resort

Treehouse Private Village Barnacle Resort
Long Beach Estates
8.6 out of 10, Excellent, (4 reviews)
"Communication from host is great. They left a bottle of wine and snacks for us to enjoy the beautiful sunsets. This place is so peaceful and clean. I would stay at this place again."
United States
Tina S.
The price is CA $550
CA $809 total
includes taxes & fees
May 12 - May 13
Treehouse Private Village Barnacle Resort

Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is CA $470
CA $689 total
includes taxes & fees
May 13 - May 14
Ocean View Suite Barnacle Resort

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (309 reviews)
"We love the accommodations and ability to cook with a full kitchen."
United States
Cheryl
The price is CA $179
CA $393 total
includes taxes & fees
May 19 - May 20
Yacht Haven Marina

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (222 reviews)
"We had a wonderful vacation!"
United States
Yuanfen
The price is CA $256
CA $509 total
includes taxes & fees
May 16 - May 17
Aqua Lodge Rentals At Coconut Cay

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,192 reviews)
"Ocean view from room balcony."
United States
Brian
The price is CA $126
CA $171 total
includes taxes & fees
Jun 1 - Jun 2
Knight's Key Suites

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (970 reviews)
"Came here for our honeymoon, we absolutely loved it! Clean, the bar and food truck was perfect."
United States
Izabella
The price is CA $150
CA $169 total
includes taxes & fees
May 13 - May 14
Tropical Cottages

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,262 reviews)
"The staff was very nice, our room was spacious and comfortable, the area has lots to do"
United States
Carol
The price is CA $251
CA $338 total
includes taxes & fees
May 31 - Jun 1
Skipjack Resort & Marina

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (61 reviews)
"The location was very good and the host was responsive. "
United States
Lilly A.
The price is CA $277
CA $549 total
includes taxes & fees
May 14 - May 15
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Brand New Marina Suite with Pool + Free Breakfast

Brand New Marina Suite with Pool + Free Breakfast
Marathon
10.0 out of 10, Exceptional, (1 review)
"Very clean and convenient to shops and restaurants "
United States
JOHN
The price is CA $288
CA $630 total
includes taxes & fees
May 12 - May 13
Brand New Marina Suite with Pool + Free Breakfast

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (185 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is CA $302
CA $614 total
includes taxes & fees
May 12 - May 13
Waterfront Home

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 CA $244
CA $792 total
includes taxes & fees
May 12 - May 13
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Canal Front Luxury Condo with Pool + Breakfast

Canal Front Luxury Condo with Pool + Breakfast
Marathon
9.8 out of 10, Exceptional, (27 reviews)
"Our stay was very pleasant! Arrival and departure were prearranged which was so easy. The place was well stocked with necessities, well kept, and quiet. We enjoyed the tiki bar. Being centrally located, we visited the many local restaurants and sights. There is a grocery store nearby. We were able to rent a pontoon boat on site for the day - very convenient.Thank you, Kate, for following up to assure our stay met all our expectations from start to finish. "
United States
Susan S.
The price is CA $176
CA $542 total
includes taxes & fees
May 12 - May 13
Canal Front Luxury Condo with Pool + Breakfast

Sombrero Beach Tropical Getaway in the Heart of Marathon

Sombrero Beach Tropical Getaway in the Heart of Marathon
Marathon
9.8 out of 10, Exceptional, (21 reviews)
"The location and nightly entertainment. "
United States
Robert H.
The price is CA $182
CA $489 total
includes taxes & fees
May 13 - May 14
Sombrero Beach Tropical Getaway in the Heart of Marathon
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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Top Big Pine Key Hotel Reviews

Find out more about Big Pine Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Big Pine Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Big Pine Key?

Yes, there are vacation rentals in Big Pine Key close to Blue Hole, or you can go with a more secluded option if you're looking for a relaxing stay. Big Pine Key is known for its beaches.

What are some of the best vacation rentals that Big Pine Key has to offer?

Sugarloaf Key RV Resort & Cottages: This vacation home rental near Big Pine Key is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Big Pine Key?

With 141 Expedia vacation rentals, you're sure to find just the right place for your Big Pine Key stay.

What can I see and do in Big Pine Key?

Family-friendly attractions include Blue Hole and Big Munson Island, whereas Florida Keys Beaches and Calusa Beach are a couple of great spots to enjoy the outdoors. Other places in town to visit include Bahia Honda State Park and Big Pine Key Flea Market.

What are vacation rentals like in Big Pine Key?

Vacation rentals are privately owned properties you can stay in for several days or more in Big Pine Key. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips.