Condo
10.0(13 Reviews)
2 Bedrooms
4 Guests
Parking
Pool
Spa
Balcony/Terrace
US $254/Night
7 Nights - US $1,776
Plantation Key Holiday Rentals
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Compare Villas, Resorts, & Rentals in Plantation Key
10.0
US $333/Night
7 Nights - US $2,331
House
10.0(8 Reviews)
2 Bedrooms
6 Guests
Oceanfront- Parking
Ocean View
View
US $244/Night
7 Nights - US $1,710
US $1,125/Night
7 Nights - US $7,875
House
10.0(2 Reviews)
2 Bedrooms
11 Guests
Hot Tub- Parking
- Ocean View
- Balcony/Terrace
US $494/Night
7 Nights - US $3,456
House
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $422/Night
7 Nights - US $2,954
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $268/Night
7 Nights - US $1,876
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
US $271/Night
7 Nights - US $1,894
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $200/Night
7 Nights - US $1,401
Luxury Holiday Rentals in Plantation Key
Over 175+ Luxury Holiday Rentals in or Near Plantation Key
House
3 Bedrooms
6 Guests
Private Pool- Parking
- Pool
- Ocean View
US $3,558/Night
7 Nights - US $24,907
House
10.0(10 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,333/Night
7 Nights - US $9,331
House
5 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,266/Night
7 Nights - US $8,865
House
10.0(39 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,253/Night
7 Nights - US $8,770
House
4 Bedrooms
15 Guests
- Air Conditioner
Internet
Pet Friendly
Child Friendly
US $1,187/Night
7 Nights - US $8,309
House
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,162/Night
7 Nights - US $8,137
House
5 Bedrooms
10 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,140/Night
7 Nights - US $7,978
House
10.0(4 Reviews)
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,005/Night
7 Nights - US $7,034
Apartment
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $997/Night
7 Nights - US $6,980
Top-Rated Holiday Rentals with a Pool in Plantation Key
Over 99+ The Best Private Villas and Holiday Rentals in Plantation Key with a Pool
House
10.0(20 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $446/Night
7 Nights - US $3,122
House
10.0(19 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $658/Night
7 Nights - US $4,603
House
10.0(10 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $597/Night
7 Nights - US $4,179
House
10.0(10 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $493/Night
7 Nights - US $3,450
House
10.0(8 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $738/Night
7 Nights - US $5,169
House
10.0(7 Reviews)
4 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $737/Night
7 Nights - US $5,158
Villa
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $534/Night
7 Nights - US $3,735
House
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $517/Night
7 Nights - US $3,618
House
10.0(5 Reviews)
5 Bedrooms
12 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $510/Night
7 Nights - US $3,569
Pet-Friendly Holiday Rentals in Plantation Key
Over 66+ Pet-Friendly Holiday Rentals in or Near Plantation Key
House
8.6(4 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $355/Night
7 Nights - US $2,487
US $416/Night
7 Nights - US $2,915
Villa
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $344/Night
7 Nights - US $2,407
House
2 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $279/Night
7 Nights - US $1,950
House
10.0(4 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $609/Night
7 Nights - US $4,263
Villa
10.0(3 Reviews)
5 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $540/Night
7 Nights - US $3,782
House
10.0(3 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $418/Night
7 Nights - US $2,929
House
10.0(3 Reviews)
3 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $315/Night
7 Nights - US $2,205
House
10.0(2 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $429/Night
7 Nights - US $3,001
Large Holiday Rentals and Private Villas in Plantation Key
Over 39+ Large Holiday Rentals and Private Villas in or Near Plantation Key
House
10.0(5 Reviews)
4 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $376/Night
7 Nights - US $2,630
House
9.8(9 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $818/Night
7 Nights - US $5,724
Apartment
9.6(24 Reviews)
3 Bedrooms
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $300/Night
7 Nights - US $2,101
US $761/Night
7 Nights - US $5,324
US $748/Night
7 Nights - US $5,234
House
3 Bedrooms
10 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $586/Night
7 Nights - US $4,102
House
5 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $556/Night
7 Nights - US $3,894
US $375/Night
7 Nights - US $2,628
House
4 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $372/Night
7 Nights - US $2,601
Wheelchair Accessible Holiday Homes in Plantation Key
Over 12+ Wheelchair Accessible Holiday Homes in or Near Plantation Key
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $739/Night
7 Nights - US $5,171
Condo
7.0(2 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,639
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Spa
US $184/Night
7 Nights - US $1,286
Condo
9.6(7 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $132/Night
7 Nights - US $924
House
6.0(1 Review)
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,960/Night
7 Nights - US $13,720
Villa
5 Bedrooms
12 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $2,500/Night
7 Nights - US $17,500
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $190/Night
7 Nights - US $1,332
House
9.8(13 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $599/Night
7 Nights - US $4,193
House
5 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,865/Night
7 Nights - US $13,054
Plantation Key Private Villas and Holiday Homes Under $200
Over 14+ Plantation Key Private Villas and Holiday Homes Under $200
House
2 Bedrooms
6 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $169/Night
7 Nights - US $1,182
Apartment
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $147/Night
7 Nights - US $1,029
Apartment
1 Bedroom
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $102/Night
7 Nights - US $711
House
10.0(2 Reviews)
3 Bedrooms
7 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $182/Night
7 Nights - US $1,271
House
10.0(8 Reviews)
4 Bedrooms
8 Guests
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $160/Night
7 Nights - US $1,120
Cottage
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $152/Night
7 Nights - US $1,063
US $180/Night
7 Nights - US $1,260
House
9.4(25 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $194/Night
7 Nights - US $1,355
US $190/Night
7 Nights - US $1,333
Instantly Bookable Holiday Homes in Plantation Key
Over 48+ Instantly Bookable Holiday Homes in or Near Plantation Key
House
10.0(2 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $204/Night
7 Nights - US $1,428
House
9.6(67 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $955/Night
7 Nights - US $6,687
House
4 Bedrooms
9 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $705/Night
7 Nights - US $4,932
House
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- View
US $399/Night
7 Nights - US $2,795
Condo
3 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $270/Night
7 Nights - US $1,891
Apartment
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $227/Night
7 Nights - US $1,590
House
10.0(8 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $206/Night
7 Nights - US $1,444
House
10.0(1 Review)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $644/Night
7 Nights - US $4,510
House
10.0(1 Review)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $206/Night
7 Nights - US $1,442
Book a Last Minute Place to Stay in Plantation Key
About Casai's Private Villas and Holiday Rentals in Plantation Key
Discover more than 184 vacation rentals available in Plantation 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 Plantation Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Plantation 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 Plantation Key. On average, places to stay near Plantation Key offer 972.45 ft², with nightly prices averaging US $597.
With Casai, finding and comparing holiday rentals in Plantation 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 near the Plantation Key, FL
There are 184 Plantation Key, FL Holiday Rentals
- Prices for a holiday home in Plantation Key start at US $102
- Top rated vacation home in Plantation Key is Venetian Shores Waterfront with Ocean Access, Pool
- Most popular short term in Plantation Key is Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
- Cheapest place to stay in Plantation Key is Turnkey Modern Studio in the Upper Keys – Stylish, Bright & Fully Equipped!
- Most expensive holiday rental in Plantation Key is Casa Margarita Islamorada, Paradise awaits!
Frequently Asked Questions About Plantation Key?
What are the top holiday rentals in Plantation Key?
With numerous options available in Plantation Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Plantation Key:
- Venetian Shores Waterfront with Ocean Access, Pool
- Sunsets on the bay at Villa Mia
- Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
- Oceanfront condo in Islamorada, amazing sunrise views, renovated in 2019!
- Best Canal in the Keys! 4/3 Waterfront,Heated Pool, Ocean access, Dock, 5⭐ Rated
- Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
- Islamorada Oasis, Luxurious 4 bedroom 3 bath home. Heated pool! Boat Lift option
- " Endless Summer" Awaits!
- Canalfront, Dog-Friendly Home with High-Speed WiFi, Private Boat Ramp, and Kayak
- Waterfront Home With Swimming Pool
How many holiday rentals have private pools in Plantation Key?
Discover a selection of holiday rentals with private pools near Plantation 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 Plantation Key are best for families?
If you're searching for a family-friendly holiday home in Plantation Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Plantation Key:
How many Casai.com holiday rentals are available in Plantation Key?
As of 2026, Casai boasts over 184 properties listed in the Plantation Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Plantation Key.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Venetian Shores Vacation Rentals in Florida | 34 |
| Indian Waterways Vacation Rentals in Florida | 647 |
| Sunshine Estates Vacation Rentals in Florida | 1184 |
| Seabreeze Trailer Park Vacation Rentals in Florida | 833 |
| Plantation Tropical Park Vacation Rentals in Florida | 1170 |
| Plantation by the Sea Vacation Rentals in Florida | 745 |
| Plantation Lake Estates Vacation Rentals in Florida | 709 |
