Big Pine Key Holiday Rentals

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Holiday Rentals in Big Pine Key

2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (124)
"Amazing stay in a boat!"
The price is NZ$419
includes taxes & fees
29 May - 30 May
Old Wooden Bridge Resort and Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Fridge, microwave, oven, stovetop
Keys 3 Bedroom Corner Home near Beach & Key West
9.4 out of 10, Exceptional, (3)
"Absolutely lovely property. The only thing we regretted was not having more time to spend there. We loved the nearby restaurant called “The Boardwalk Pub & Grill. They have a very friendly staff and they’re very accommodating in the changes they make to their menu."
The price is NZ$1,176
includes taxes & fees
28 May - 29 May
Keys 3 Bedroom Corner Home near Beach & Key West
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Pool
Tropical Caribbean Wonderland
9.2 out of 10, Wonderful, (73)
"We are pop up campers, so the RV was quite a step up and a perfect match for us. Only really spent the nighttime and morning hours in the RV. Bed was super comfy and CLEAN (a big plus for me as I am very picky). Quiet neighborhood. Slept like a baby. Was confused about the toilet and paper so we used the resort’s restroom. Would definitely book here again."
Tropical Caribbean Wonderland
Outdoor pool, pool loungers
Skipjack Resort & Marina
3.0 star property
8.6 out of 10, Excellent, (1095)
"Our stay was overall great. We would stay at Skip Jacks again. The floor in our suite could use a good vacuum and mopping. "
The price is NZ$480
includes taxes & fees
28 May - 29 May
Skipjack Resort & Marina
Front of property
Aqua Lodge Rentals At Coconut Cay
3.5 star property
9.6 out of 10, Exceptional, (104)
"highly recommended, very clean ,pace full and nice place "
The price is NZ$532
includes taxes & fees
28 May - 29 May
Aqua Lodge Rentals At Coconut Cay
Superior Bungalow, Ensuite (Cottage 04) | Exterior
Tropical Cottages
3.0 star property
8.4 out of 10, Very good, (685)
"Weather was prefect. There’s a lot of bugs and cottage 9 does NOT have a stove. Most street noise but nothing to loud "
The price is NZ$219
includes taxes & fees
11 Jun - 12 Jun
Tropical Cottages
Outdoor pool, pool loungers
Knight's Key Suites
3.0 star property
9.0 out of 10, Wonderful, (1029)
"Wonderful location, next to 7 miles bridge and a look out see restaurant. "
The price is NZ$254
includes taxes & fees
3 Jun - 4 Jun
Knight's Key Suites
Standard Bungalow | Living area
Yacht Haven Marina
3.5 star property
9.8 out of 10, Exceptional, (48)
"The house boat was beautiful, clean and the patio over looking the lagoon was very relaxing. There are manatees that visit too. :) The neighbors are very friendly, as is the staff. The kayaks and bicycles are included in the rental, which is fantastic. The location s very close to groceries and local parks. We took an airplane scenic ride which was the highlight of the trip. The small airport is only 3 miles away. We will come back to Yacth Haven !"
The price is NZ$462
includes taxes & fees
4 Jun - 5 Jun
Yacht Haven Marina
Exclusive Cabin | Living area
Cabins at Bonefish Bay
3.0 star property
10.0 out of 10, Exceptional, (9)
"Our group arrived not knowing what to expect after a long days travel, as soon as we pulled into the office to get our keys we were amazed at quaint cabin that awaited us. It was super easy to get the keys after hours. The cabin itself was perfect!!!! Plenty of room for a group of 5. The towels provided were perfect for the relaxing pool area. Every thing we would need for cooking was already in the cabin. The rooms were clean and bright with natural wood. The area was quiet and very well...
Cabins at Bonefish Bay
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Beach nearby
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
10.0 out of 10, Exceptional, (191)
"We just wanted a short vacation getaway. It was great. We rented a boat and spent our time in the water. Great time with friends."
Life in Paradise w/ Boat Slip at #1 Rated Resort in Marathon - Coral Lagoon
Balcony
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (203)
"Overall, a very nice property in a good location, with good amenities. Located near several good Restaurants, especially the Square Grouper. Communication with Host was very good."
The price is NZ$725
includes taxes & fees
30 May - 31 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Property grounds
Old Florida Style, wrap around porch, boat basin for dockage, open water
9.8 out of 10, Exceptional, (45)
"We brought a boat with us. The protected bay is perfect with a marked channel (note it is a tight turn to get in during high winds with shallow spots). Plenty of room for a trailer. The view here is very peaceful and we loved sitting out on the break-wall. We all slept comfortable and appreciated that each room had their own AC unit for control. The restaurant that is walking distance had great food, drinks, and live music. Minor thing, but my group wanted it passed along that the toaster needs...
Old Florida Style, wrap around porch, boat basin for dockage, open water
Exterior
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (185)
"Highly recommend"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Pool
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Exterior
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (48)
"Layout of house and location are perfect. The owners were very communicative and responsive."
The price is NZ$2,170
includes taxes & fees
28 May - 29 May
One of the very few beach houses with a daily, rental license in the Keys.
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Property grounds
Southern Diversion Estate-see our reduced rates
10.0 out of 10, Exceptional, (82)
"We were celebrating my wife’s 40th birthday. There were 17 people in our group. Adults and children. Something for everyone to do. We enjoyed relaxing at the property by the pools, fishing from the dock, kayaking and paddle boarding. We went scuba diving with better than most scuba, deep sea fishing on the tail walker. We hired chef Heather for several dinners. It was an amazing trip."
Southern Diversion Estate-see our reduced rates
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See all available properties in Big Pine 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.

Other types of properties in Big Pine Key you may be interested in

2 Bedroom Aqua Lodge # 13 Barracuda | Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (124)
"Amazing stay in a boat!"
The price is NZ$419
includes taxes & fees
29 May - 30 May
Old Wooden Bridge Resort and Marina
Sundeck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (130)
"Nice place, very clean and quiet. The chair and sofa bed was peeling and the kitchen ledge is uneven so we almost fell."
Sunshine Key RV Resort & Marina
Property grounds
Barnacle Bed and Breakfast
2.0 star property
8.0 out of 10, Very good, (15)
"The location of the property was great and we saw the key deer on property and nearby. The room and bathroom were very nicely decorated and clean. The bed was comfortable. The beach front area had some trash that needed to be picked up and the home could use some landscaping. We did not stay for the continental breakfast so can not speak to that. Check in was a little challenging; I did not receive the e-mail day before check-in that I was expecting but did receive a phone call. However,...
The price is NZ$514
includes taxes & fees
12 Jun - 13 Jun
Barnacle Bed and Breakfast
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Big Pine Key holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Big Pine Key. 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 Big Pine Key. 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 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 holiday 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 Big Pine Key short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Big Pine Key?

Yes, there are holiday rentals in Big Pine Key close to Key West Visitors Center, or you can select 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 holiday rentals that Big Pine Key has to offer?

Aqua Lodge Rentals At Coconut Cay: This holiday home rental outside of Big Pine Key is located near the beach, and offers an outdoor pool, air conditioning and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

How many holiday rentals are there in Big Pine Key?

With 146 Expedia holiday rentals, you're guaranteed 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 Key West Visitors Center and Blue Hole, whereas Calusa Beach and Bahia Honda State Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Florida Keys Beaches and Big Pine Key Flea Market.

What are holiday rentals like in Big Pine Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Big Pine Key. Holiday rentals feature extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip.

Recent reviews of Big Pine Key properties
Expedia verified reviews