House
10.0(65 Reviews)
2 Bedrooms
6 Guests
Parking
Ocean View
Balcony/Terrace
View
US $169/Night
7 Nights - US $1,180
Big Pine Key Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Big Pine Key
10.0
Bed & Breakfast
9.8(5 Reviews)
4 Bedrooms
6 Guests
Private Beach
Oceanfront
Hot Tub
Breakfast
US $495/Night
7 Nights - US $3,465
House
8.8(180 Reviews)
1 Bedroom
Pool- Balcony/Terrace
Kitchen
Air Conditioner
US $343/Night
7 Nights - US $2,402
House
10.0(12 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $248/Night
7 Nights - US $1,735
Apartment
9.4(6 Reviews)
5 Bedrooms
16 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $413/Night
7 Nights - US $2,890
House
10.0(11 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $206/Night
7 Nights - US $1,443
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $510/Night
7 Nights - US $3,567
House
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $270/Night
7 Nights - US $1,892
House
10.0(7 Reviews)
2 Bedrooms
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $201/Night
7 Nights - US $1,409
Luxury Holiday Rentals in Big Pine Key
Over 303+ Luxury Holiday Rentals in or Near Big Pine Key
US $7,000/Night
7 Nights - US $49,000
House
9.6(80 Reviews)
5 Bedrooms
10 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $1,235/Night
7 Nights - US $8,648
House
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,150/Night
7 Nights - US $8,051
US $1,148/Night
7 Nights - US $8,037
House
5 Bedrooms
10 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
US $1,123/Night
7 Nights - US $7,863
House
10.0(34 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- View
US $1,066/Night
7 Nights - US $7,460
House
3 Bedrooms
7 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $995/Night
7 Nights - US $6,962
House
9.4(6 Reviews)
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $987/Night
7 Nights - US $6,907
House
10.0(65 Reviews)
4 Bedrooms
9 Guests
- Private Pool
- Parking
- Pool
- Kitchen
US $968/Night
7 Nights - US $6,779
Top-Rated Holiday Rentals with a Pool in Big Pine Key
Over 106+ The Best Private Villas and Holiday Rentals in Big Pine Key with a Pool
House
10.0(66 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $828/Night
7 Nights - US $5,795
House
10.0(15 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $595/Night
7 Nights - US $4,163
House
10.0(9 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $628/Night
7 Nights - US $4,398
House
10.0(9 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $428/Night
7 Nights - US $2,993
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $648/Night
7 Nights - US $4,539
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $592/Night
7 Nights - US $4,145
House
10.0(8 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $486/Night
7 Nights - US $3,401
House
10.0(6 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- View
US $294/Night
7 Nights - US $2,057
House
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $283/Night
7 Nights - US $1,981
Pet-Friendly Holiday Rentals in Big Pine Key
Over 143+ Pet-Friendly Holiday Rentals in or Near Big Pine Key
House
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,765
House
9.4(6 Reviews)
2 Bedrooms
7 Guests
- Parking
- Internet
Pet Friendly- Child Friendly
US $310/Night
7 Nights - US $2,170
Cottage
8.6(374 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $250/Night
7 Nights - US $1,752
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $323/Night
7 Nights - US $2,264
House
8.9(20 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $238/Night
7 Nights - US $1,666
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $161/Night
7 Nights - US $1,124
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $273/Night
7 Nights - US $1,914
House
10.0(1 Review)
2 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $273/Night
7 Nights - US $1,909
House
10.0(1 Review)
2 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $248/Night
7 Nights - US $1,738
Large Holiday Rentals and Private Villas in Big Pine Key
Over 37+ Large Holiday Rentals and Private Villas in or Near Big Pine Key
Villa
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,307
Cabin
8.0(315 Reviews)
47 Bedrooms
150 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $235/Night
7 Nights - US $1,646
House
10.0(4 Reviews)
5 Bedrooms
12 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $446/Night
7 Nights - US $3,122
US $831/Night
7 Nights - US $5,820
House
10.0(4 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $430/Night
7 Nights - US $3,007
House
10.0(3 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $557/Night
7 Nights - US $3,899
House
10.0(2 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $744/Night
7 Nights - US $5,209
House
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $573/Night
7 Nights - US $4,011
House
10.0(2 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $472/Night
7 Nights - US $3,307
Big Pine Key Private Villas and Holiday Homes Under $200
Over 43+ Big Pine Key Private Villas and Holiday Homes Under $200
House
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $172/Night
7 Nights - US $1,207
US $150/Night
7 Nights - US $1,050
House
9.4(15 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $196/Night
7 Nights - US $1,371
US $164/Night
7 Nights - US $1,148
House
9.2(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $164/Night
7 Nights - US $1,148
House
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
8.0(5 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $155/Night
7 Nights - US $1,088
House
8.0(3 Reviews)
2 Bedrooms
4 Guests
- Ocean View
- View
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,306
House
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,357
House
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $191/Night
7 Nights - US $1,340
Instantly Bookable Holiday Homes in Big Pine Key
Over 146+ Instantly Bookable Holiday Homes in or Near Big Pine Key
House
10.0(5 Reviews)
2 Bedrooms
7 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $228/Night
7 Nights - US $1,594
US $249/Night
7 Nights - US $1,746
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $213/Night
7 Nights - US $1,493
House
9.6(4 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $236/Night
7 Nights - US $1,652
House
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
9.4(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $249/Night
7 Nights - US $1,745
RV Rental
8.6(11 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $327/Night
7 Nights - US $2,286
Cabin
8.6(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $725/Night
7 Nights - US $5,073
Apartment
8.0(7 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $510/Night
7 Nights - US $3,569
RV Rental
6.4(6 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $381/Night
7 Nights - US $2,668
Book a Last Minute Place to Stay in Big Pine Key
About Casai's Private Villas and Holiday Rentals in Big Pine Key
Discover more than 312 vacation rentals available in Big Pine Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Big Pine Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Big Pine Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Big Pine Key. On average, places to stay near Big Pine Key offer 821.55 ft², with nightly prices averaging US $389.
With Casai, finding and comparing holiday rentals in Big Pine Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Big Pine Key, FL
There are 312 Big Pine Key, FL Holiday Rentals
- Prices for a holiday home in Big Pine Key start at US $150
- Top rated vacation home in Big Pine Key is Island Sunrise Resort- 3 acre estate with open water sunrises.
- Most popular short term in Big Pine Key is Big Pine Key Motel
- Cheapest place to stay in Big Pine Key is Go Fish Inn
- Most expensive holiday rental in Big Pine Key is Florida Keys /Big Pine Key/ Dear Haven
Recently Booked Holiday Rentals in Big Pine Key
Frequently Asked Questions About Big Pine Key?
What are the top holiday rentals in Big Pine Key?
With numerous options available in Big Pine Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Big Pine Key:
- Island Sunrise Resort- 3 acre estate with open water sunrises.
- Awesome Open Water View at Blue Heron Estate
- Captain D's Hideout - Beautiful waterfront home in the heart of a deer preserve
- Fishermen's Paradise | Pool, 220' Dock & Open-Water Views
- Big Pine Key Waterfront Home: Boating, Sunrises, Sunsets; Relax in Paradise!
- BRILLIANT VIEWS OF OPEN WATERS- 75' DOCK - 250 ' TO OPEN CHANNEL BIG PINE KEY FL
- Fisherman’s Paradise - Ocean & Gulf Access! Key Deer Preserve. TIME TO FISH!
- Gorgeous Beachfront Home with a pool. Water views from every direction.
- "Canal-Front Paradise in Big Pine Key-Relax &Explore the keys"
- Excellent boating location-65 ft frontage on deep canal
How many holiday rentals have private pools in Big Pine Key?
Discover a selection of holiday rentals with private pools near Big Pine Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Big Pine Key are best for families?
If you're searching for a family-friendly holiday home in Big Pine Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Big Pine Key:
How many Casai.nz holiday rentals are available in Big Pine Key?
As of 2026, Casai boasts over 312 properties listed in the Big Pine Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Big Pine Key.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Eden Pines Vacation Rentals in Big Pine Key, Florida | 454 |
| Doctor's Arm Vacation Rentals in Big Pine Key, Florida | 317 |
| Long Beach Estates Vacation Rentals in Big Pine Key, Florida | 181 |
| Port Pine Heights Vacation Rentals in Big Pine Key, Florida | 114 |
| Pine Channel Estates Vacation Rentals in Big Pine Key, Florida | 493 |
| Sands Vacation Rentals in Big Pine Key, Florida | 371 |
| Whispering Pines Vacation Rentals in Big Pine Key, Florida | 396 |
| Punta Brisa Vacation Rentals in Big Pine Key, Florida | 317 |
| Lambert Vacation Rentals in Big Pine Key, Florida | 301 |
| Tropical Bay Estates Vacation Rentals in Big Pine Key, Florida | 347 |
| Atlantis Estates Vacation Rentals in Big Pine Key, Florida | 375 |
