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

Big Pine Key Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Big Pine Key holiday rentals

Living area

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (355 reviews)
"We had a great time! It was family, friendly, and we saw a ton of key deer. Pool was perfect as well!"
United States
Maya
The price is HK$805
HK$2,008 total
includes taxes & fees
3 Aug - 4 Aug
Old Wooden Bridge Resort and Marina
Interior

🌴 TROPICAL RETREAT 🌴 RV In The Keys

🌴 TROPICAL RETREAT 🌴 RV In The Keys
Big Pine Key
8.8 out of 10, Excellent, (9 reviews)
"The RV was well outfitted with the essentials needed for the 2 days we stayed. It was dated, with some upkeep needed on the shower door and sofa but it was comfortable and clean. Heather was a pleasure to deal with, was responsive and communicated very well."
Canada
Graham B.
The price is HK$1,051
HK$2,575 total
includes taxes & fees
27 Jul - 28 Jul
🌴 TROPICAL RETREAT 🌴 RV In The Keys
Interior

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 HK$1,560
HK$2,367 total
includes taxes & fees
22 Jul - 23 Jul
Star Room Barnacle Resort
Terrace/patio

LARGE LOT & RV Fisherman Camp

LARGE LOT & RV Fisherman Camp
Big Pine Key
6.4 out of 10, (6 reviews)
"Property was as described, very comfortable and close to family on Summerland Key. Deer walking through the park was a nice perk"
United States
Pauline A.
The price is HK$1,404
HK$3,027 total
includes taxes & fees
27 Jul - 28 Jul
LARGE LOT & RV Fisherman Camp
Interior

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
8.4 out of 10, Very good, (12 reviews)
"This place was perfect for our family. Just the right distance between Marathon and Key West. Would definitely recommend it to anyone looking for a place to stay"
United States
Robert C.
The price is HK$1,795
HK$4,782 total
includes taxes & fees
17 Aug - 18 Aug
Charming 3-bedroom house in Big Pine Key near Beach and Key West
Outdoor pool

Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool

Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool
Big Pine Key
10.0 out of 10, Exceptional, (5 reviews)
"It was a really nice place . My partner and I came here to elope highly recommended this place . "
United States
josh e.
The price is HK$2,744
HK$5,400 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 2-bedroom house in charming Big Pine Key with canal view and relaxing pool
Interior

Beach View Room Dormitory Room Barnacle Resort

Beach View Room Dormitory Room Barnacle Resort
Long Beach Estates
The price is HK$2,579
HK$3,822 total
includes taxes & fees
22 Jul - 23 Jul
Beach View Room Dormitory Room Barnacle Resort
Interior

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 HK$3,152
HK$5,635 total
includes taxes & fees
22 Jul - 23 Jul
Treehouse Private Village Barnacle Resort
Smart TV

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views

Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Big Pine Key
10.0 out of 10, Exceptional, (31 reviews)
"A beautiful house with everything you need to have a great time"
United States
David T.
The price is HK$7,549
HK$14,038 total
includes taxes & fees
16 Aug - 17 Aug
Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
Interior

Ocean View Suite Barnacle Resort

Ocean View Suite Barnacle Resort
Long Beach Estates
The price is HK$2,697
HK$3,942 total
includes taxes & fees
22 Jul - 23 Jul
Ocean View Suite Barnacle Resort
Exterior

Yacht Haven Marina

Yacht Haven Marina
3.5 star property
Marathon
9.8 out of 10, Exceptional, (339 reviews)
"Perfect place for our family! Our boys love fishing and outdoors. They loved being able to wake up to watch baby dolphins/sharks swim in the water. We spotted one manitee"
United States
Yanzhu
The price is HK$1,023
HK$2,253 total
includes taxes & fees
4 Aug - 5 Aug
Yacht Haven Marina
Premium bedding, soundproofing, iron/ironing board, free WiFi

Knight's Key Suites

Knight's Key Suites
3.0 star property
Marathon
9.0 out of 10, Wonderful, (1,214 reviews)
"The rooms are always clean, no bugs, and walking distance to Sunset Grill."
United States
Cristina
The price is HK$702
HK$959 total
includes taxes & fees
9 Aug - 10 Aug
Knight's Key Suites
Exterior

Tropical Cottages

Tropical Cottages
3.0 star property
Marathon
8.6 out of 10, Excellent, (988 reviews)
"Very well kept-nice cottage! Would book again!"
United States
Susan
The price is HK$855
HK$961 total
includes taxes & fees
17 Aug - 18 Aug
Tropical Cottages
BBQ/picnic Area

Aqua Lodge Rentals At Coconut Cay

Aqua Lodge Rentals At Coconut Cay
3.5 star property
Marathon
9.6 out of 10, Exceptional, (227 reviews)
"I never give 5 stars but it was as advertised and good pricing and fun little spot. Keep it up folks.."
Canada
Wesley
The price is HK$906
HK$2,224 total
includes taxes & fees
22 Jul - 23 Jul
Aqua Lodge Rentals At Coconut Cay
Outdoor pool, pool loungers

Skipjack Resort & Marina

Skipjack Resort & Marina
3.0 star property
Marathon
8.6 out of 10, Excellent, (1,282 reviews)
"I will stay here again"
United States
Peter
The price is HK$1,192
HK$1,659 total
includes taxes & fees
16 Aug - 17 Aug
Skipjack Resort & Marina
A heated pool

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$1,317
HK$4,438 total
includes taxes & fees
17 Aug - 18 Aug
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Beach

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
The price is HK$1,029
HK$4,051 total
includes taxes & fees
16 Aug - 17 Aug
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Coffee/tea maker, fridge, microwave, oven

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is HK$1,686
HK$4,159 total
includes taxes & fees
17 Aug - 18 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is HK$1,333
HK$2,338 total
includes taxes & fees
22 Jul - 23 Jul
Seabreeze Escape WF RV Lot 489
A heated pool

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$1,441
HK$4,584 total
includes taxes & fees
23 Jul - 24 Jul
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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

Rainbow Bend Resort

Rainbow Bend Resort

8/10 Good
"Nice place"
Venkata 2-night trip
Posted 3 hours ago
Rainbow Bend Resort

Find out more about Big Pine Key

Search for holiday rentals in Big Pine Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Big Pine Key using one of the methods below:

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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.

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

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of 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 holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Big Pine Key?

With 139 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.