A calm river with boats, lush greenery, and a clear blue sky.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Big Pine Key holiday rentals

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is 5.024.034 ₫
9.303.226 ₫ total
includes taxes & fees
17 Oct - 18 Oct
Old Wooden Bridge Resort and Marina
A hotel room with two beds, each with a wooden headboard, white bedding, and a bedside table with a lamp.

2. Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,237 reviews)
"Clean room with exceptional hospitality"
United States
chantal
The price is 2.151.117 ₫
2.978.070 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Knight's Key Suites
An outdoor seating area with wicker furniture and cushions, a thatched-roof structure, and lush greenery.

3. Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,002 reviews)
"Cute little cottage perfect for couples had an amazing stay and will definitely be back to tropical cottages again"
United States
Aaron
The price is 2.051.156 ₫
2.307.680 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Tropical Cottages
A nighttime pool area with a clear view of the pool, surrounding palm trees, and a building with a sign.

4. Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,290 reviews)
"Great spot"
Canada
Justin
The price is 4.651.943 ₫
6.285.382 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Skipjack Resort & Marina
A resort with a pool, lounge chairs, and a view of the ocean.

5. Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort

Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
2.5 star property
Marathon
9.2 out of 10, Wonderful, (145 reviews)
"It is an excellent place."
United States
Arianna
The price is 4.651.943 ₫
5.964.086 ₫ total
includes taxes & fees
3 Oct - 4 Oct
Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
A marina with several docked boats and a row of small, white cabins with blue roofs.

6. Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.6 out of 10, Exceptional, (364 reviews)
"Clean Friendly staff Recommend for family"
United States
Yamei
The price is 3.950.645 ₫
8.097.070 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Yacht Haven Marina
Exterior

7. Aqua Lodges at 47th Street Gulfside

Aqua Lodges at 47th Street Gulfside
3.0 star property
Marathon
8.8 out of 10, Excellent, (59 reviews)
"Loved our stay at the aqua lodges 10/10 would do it again"
United States
Lauren
The price is 3.038.724 ₫
7.071.158 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Aqua Lodges at 47th Street Gulfside
A beach with palm trees, a sandy path, and beach chairs.

8. Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (236 reviews)
"Never stayed in a houseboat before. It was a novel experience!"
United States
Susan
The price is 3.209.843 ₫
7.624.773 ₫ total
includes taxes & fees
4 Oct - 5 Oct
Aqua Lodge Rentals At Coconut Cay
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

Isla Bella Beach Resort & Spa

Isla Bella Beach Resort & Spa

10/10 Excellent
"Isla Bella Beach Resort exceeded every single expectation! From the moment we arrived, the property felt like a true island paradise. Our room was spotlessly clean, amazingly comfortable, and provided the perfect sanctuary after a day in the sun. ​Every single person working on the property was wonderfully pleasant and attentive—the kind of warm, genuine hospitality that turns a good vacation into a memorable one. On top of that, the grounds were in immaculate shape; the pristine landscaping, lush palms, and pristine waterfront areas were continuously well-kept and breathtaking to walk through. ​If you are planning a trip to Marathon, do yourself a favor and book a stay here. We are already counting down the days until we can return!"
Chris 4-night trip
Posted 13 hours ago
Isla Bella Beach Resort & Spa

Frequently asked questions

Can I find holiday rentals in Big Pine Key?

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

How many holiday rentals are there in Big Pine Key?

With 148 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 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 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.