Cottage
10.0(16 Reviews)
1 Bedroom
2 Guests
Parking
Ocean View
Balcony/Terrace
View
R5,922/Night
7 Nights - R41,455
Dismal Key Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Dismal Key
10.0
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
Air Conditioner
Internet
Pet Friendly
R4,347/Night
7 Nights - R30,421
Apartment
1 Bedroom
Oceanfront- Parking
Pool- Ocean View
R3,106/Night
7 Nights - R21,739
Cottage
10.0(9 Reviews)
1 Bedroom
2 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
TV
R5,182/Night
7 Nights - R36,275
Apartment
10.0(2 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
R4,330/Night
7 Nights - R30,306
Apartment
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
R3,088/Night
7 Nights - R21,607
Apartment
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
R5,669/Night
7 Nights - R39,679
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
Breakfast- Air Conditioner
- Internet
- Child Friendly
R5,372/Night
7 Nights - R37,607
Apartment
1 Bedroom
- Oceanfront
- Parking
- Pool
- Ocean View
R3,088/Night
7 Nights - R21,607
House
10.0(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
R5,029/Night
7 Nights - R35,207
Apartment
9.2(7 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Internet
R2,330/Night
7 Nights - R16,312
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R6,587/Night
7 Nights - R46,109
R5,332/Night
7 Nights - R37,328
Apartment
9.8(60 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
R5,508/Night
7 Nights - R38,561
House
9.8(13 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R5,032/Night
7 Nights - R35,223
Apartment
9.8(11 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
R3,804/Night
7 Nights - R26,623
House
9.8(6 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R6,372/Night
7 Nights - R44,596
House
9.6(53 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
R4,667/Night
7 Nights - R32,674
Apartment
9.6(24 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
R3,905/Night
7 Nights - R27,330
R8,154/Night
7 Nights - R57,077
Boat Rental
9.4(28 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
R3,467/Night
7 Nights - R24,271
Apartment
8.8(17 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
R2,655/Night
7 Nights - R18,582
Apartment
8.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
R2,830/Night
7 Nights - R19,799
Apartment
7.6(8 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
Spa
R2,357/Night
7 Nights - R16,493
About Casai's Private Villas and Holiday Rentals in Dismal Key
Discover more than 227 vacation rentals available in Dismal 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 Dismal Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Dismal 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 Dismal Key.
With Casai, finding and comparing holiday rentals in Dismal 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.
There are 227 Dismal Key, FL Holiday Rentals
- Prices for a holiday home in Dismal Key start at R1,562
- Top rated vacation home in Dismal Key is Paradise on the Bay
- Most popular short term in Dismal Key is Cozy Cottage Goodland Fl.
- Cheapest place to stay in Dismal Key is Naples Oasis w/Screened Porch & Tennis Court!
- Most expensive holiday rental in Dismal Key is Upscale waterfront home with private dock, saltwater pool, lanai, grill, & W/D
Recently Booked Holiday Rentals in Dismal Key
Frequently Asked Questions About Dismal Key?
What are the top holiday rentals in Dismal Key?
With numerous options available in Dismal Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Dismal Key:
- Paradise on the Bay
- Luxurious Canal-Front Retreat w/Game Room!
- Cozy coastal cottage in Goodland
- Charming Home Waterfront and Pool.
- Direct panoramic waterfront views
- Harbor Place Boathouse, BRAND NEW DOCK, Open, on stilts, ocean front
- Harbor Place Boathouse BRAND NEW DOCK
- Spectacular Waterfront Home-3 Bed, 2 Bath w/Pool and Breathtaking Views!
- Elegant Coastal Townhouse with Panoramic Water Views
- Goodland Waterfront Cottage
How many Casai.co.za holiday rentals are available in Dismal Key?
As of 2026, Casai boasts over 227 properties listed in the Dismal Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Dismal Key.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Isles of Capri Vacation Rentals in Naples, Florida | 69 |
| Hammock Bay Vacation Rentals in Naples, Florida | 854 |
| Whisper Trace Vacation Rentals in Naples, Florida | 399 |
| Big Cypress Vacation Rentals in Naples, Florida | 477 |
| Mallards Landing Vacation Rentals in Naples, Florida | 364 |
| Cranberry Crossing Vacation Rentals in Naples, Florida | 368 |
