Casey Key Holiday Rentals
House
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Pet Friendly
Air Conditioner
Internet
CA $547/Night
7 Nights - CA $3,829
House
10.0Exceptional
(2 Reviews)
1 Bedroom
2 Baths
6 Guests
1603.82 ft²
Oceanfront- Fireplace/Heating
Pool
Ocean View
CA $419/Night
7 Nights - CA $2,931
Condo
9.2Exceptional
(639 Reviews)
1 Bedroom
1 Bath
- Pool
- Ocean View
Balcony/Terrace
View
CA $358/Night
7 Nights - CA $2,506
House
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
CA $428/Night
7 Nights - CA $2,997
House
- Sarasota
- ·
- Osprey Village
- 0.33 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
850.35 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $253/Night
7 Nights - CA $1,768
New
House
3 Bedrooms
2 Baths
8 Guests
1589 ft²
- Pool
- Ocean View
- View
Kitchen
CA $350/Night
7 Nights - CA $2,453
Cottage
10.0Exceptional
(160 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $263/Night
7 Nights - CA $1,841
Cottage
10.0Exceptional
(78 Reviews)
2 Bedrooms
1 Bath
4 Guests
695 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $363/Night
7 Nights - CA $2,541
Condo
10.0Exceptional
(56 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $568/Night
7 Nights - CA $3,976
Luxury Holiday Rentals in Casey Key
Over 587+ Luxury Holiday Rentals in or Near Casey Key
House
10.0Exceptional
(21 Reviews)
5 Bedrooms
5 Baths
8 Guests
5000 ft²
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
CA $5,227/Night
7 Nights - CA $36,587
House
3 Bedrooms
4 Baths
14 Guests
5767 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $3,881/Night
7 Nights - CA $27,170
House
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
10 Guests
3310 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $3,014/Night
7 Nights - CA $21,099
New
House
- Sarasota
- ·
- Sorrento Shores
- 0.21 mi to center
5 Bedrooms
4 Baths
10 Guests
2830.91 ft²
- Pet Friendly
Child Friendly
Security/Safety
CA $2,842/Night
7 Nights - CA $19,895
House
9.6Exceptional
(7 Reviews)
6 Bedrooms
4 Baths
12 Guests
4000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,444/Night
7 Nights - CA $10,108
House
4 Bedrooms
4 Baths
12 Guests
Hot Tub- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $1,401/Night
7 Nights - CA $9,809
House
9.6Exceptional
(85 Reviews)
4 Bedrooms
5 Baths
10 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
CA $1,349/Night
7 Nights - CA $9,443
House
9.2Exceptional
(18 Reviews)
4 Bedrooms
2 Baths
10 Guests
2676 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,345/Night
7 Nights - CA $9,412
House
9.8Exceptional
(11 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $1,223/Night
7 Nights - CA $8,562
Top-Rated Holiday Rentals with a Pool in Casey Key
Over 261+ The Best Private Villas and Holiday Rentals in Casey Key with a Pool
Hotel
10.0Exceptional
(261 Reviews)
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
CA $210/Night
7 Nights - CA $1,473
House
10.0Exceptional
(46 Reviews)
1 Bedroom
1 Bath
4 Guests
664 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $188/Night
7 Nights - CA $1,316
House
- Sarasota
- ·
- Sorrento Shores
- 0.16 mi to center
10.0Exceptional
(40 Reviews)
3 Bedrooms
2 Baths
6 Guests
1971 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
CA $481/Night
7 Nights - CA $3,370
House
10.0Exceptional
(36 Reviews)
1 Bedroom
1 Bath
3 Guests
700 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $260/Night
7 Nights - CA $1,820
House
10.0Exceptional
(31 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $340/Night
7 Nights - CA $2,380
House
10.0Exceptional
(25 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $387/Night
7 Nights - CA $2,712
House
10.0Exceptional
(21 Reviews)
3 Bedrooms
2 Baths
8 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $289/Night
7 Nights - CA $2,023
House
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Pool
- Ocean View
- View
CA $289/Night
7 Nights - CA $2,021
Apartment
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $566/Night
7 Nights - CA $3,962
Pet-Friendly Holiday Rentals in Casey Key
Over 269+ Pet-Friendly Holiday Rentals in or Near Casey Key
Villa
10.0Exceptional
(45 Reviews)
2 Bedrooms
1 Bath
4 Guests
850 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $233/Night
7 Nights - CA $1,633
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
301.39 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $175/Night
7 Nights - CA $1,224
House
8.0Excellent
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
944 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $319/Night
7 Nights - CA $2,231
Villa
10.0Exceptional
(20 Reviews)
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $470/Night
7 Nights - CA $3,293
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
678.13 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $147/Night
7 Nights - CA $1,031
House
10.0Exceptional
(20 Reviews)
2 Bedrooms
2 Baths
6 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $295/Night
7 Nights - CA $2,067
Condo
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $585/Night
7 Nights - CA $4,096
House
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $239/Night
7 Nights - CA $1,670
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $387/Night
7 Nights - CA $2,709
Large Holiday Rentals and Private Villas in Casey Key
Over 63+ Large Holiday Rentals and Private Villas in or Near Casey Key
Villa
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $455/Night
7 Nights - CA $3,185
Villa
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
2572.57 ft²
Private Beach- Oceanfront
- Pool
- Ocean View
CA $462/Night
7 Nights - CA $3,231
Villa
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $561/Night
7 Nights - CA $3,923
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- View
- Pet Friendly
Parking
CA $406/Night
7 Nights - CA $2,839
Villa
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $563/Night
7 Nights - CA $3,940
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $353/Night
7 Nights - CA $2,472
Villa
9.4Exceptional
(28 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $516/Night
7 Nights - CA $3,614
House
6.6Good
(4 Reviews)
2 Bedrooms
2 Baths
10 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
CA $214/Night
7 Nights - CA $1,499
Villa
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $561/Night
7 Nights - CA $3,923
Wheelchair Accessible Holiday Homes in Casey Key
Over 33+ Wheelchair Accessible Holiday Homes in or Near Casey Key
Condo
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $373/Night
7 Nights - CA $2,614
House
1 Bedroom
2 Baths
4 Guests
1550 ft²
- Fireplace/Heating
- Balcony/Terrace
- Air Conditioner
- Child Friendly
CA $167/Night
7 Nights - CA $1,169
Hotel
9.4Exceptional
(502 Reviews)
1 Bath
- Pool
- Balcony/Terrace
Breakfast- Kitchen
CA $166/Night
7 Nights - CA $1,166
House
- Sarasota
- ·
- Sorrento Shores
- 0.05 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
CA $315/Night
7 Nights - CA $2,209
Apartment
9.6Exceptional
(168 Reviews)
25 Bedrooms
7 Baths
22 Guests
507.44 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $173/Night
7 Nights - CA $1,209
Condo
9.6Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
1750 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $234/Night
7 Nights - CA $1,636
Condo
- Sarasota
- ·
- Sorrento Shores
- 0.28 mi to center
8.6Fabulous
(17 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $904/Night
7 Nights - CA $6,331
House
3 Bedrooms
2 Baths
12 Guests
3284 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $886/Night
7 Nights - CA $6,199
New
Condo
3 Bedrooms
2 Baths
8 Guests
2058 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
CA $328/Night
7 Nights - CA $2,294
Casey Key Private Villas and Holiday Homes Under $200
Over 196+ Casey Key Private Villas and Holiday Homes Under $200
Condo
10.0Exceptional
(32 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $246/Night
7 Nights - CA $1,720
Apartment
9.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
516.67 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $130/Night
7 Nights - CA $913
Hotel
9.2Exceptional
(905 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
CA $213/Night
7 Nights - CA $1,493
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
5 Guests
900 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $231/Night
7 Nights - CA $1,616
Apartment
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $247/Night
7 Nights - CA $1,729
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $236/Night
7 Nights - CA $1,656
House
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
CA $262/Night
7 Nights - CA $1,831
House
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
450 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
CA $161/Night
7 Nights - CA $1,130
Condo
- Sarasota
- ·
- Osprey Village
- 0.26 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
CA $271/Night
7 Nights - CA $1,898
Instantly Bookable Holiday Homes in Casey Key
Over 278+ Instantly Bookable Holiday Homes in or Near Casey Key
House
10.0Exceptional
(34 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $421/Night
7 Nights - CA $2,948
House
6.8Good
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
944 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $328/Night
7 Nights - CA $2,294
House
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $351/Night
7 Nights - CA $2,455
House
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $345/Night
7 Nights - CA $2,415
House
10.0Exceptional
(9 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $305/Night
7 Nights - CA $2,136
Condo
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $753/Night
7 Nights - CA $5,272
House
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
1100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $316/Night
7 Nights - CA $2,211
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Pool
- Pet Friendly
- Kitchen
- Air Conditioner
CA $387/Night
7 Nights - CA $2,709
House
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
CA $284/Night
7 Nights - CA $1,988
Book a Last Minute Place to Stay in Casey Key
About Casai's Private Villas and Holiday Rentals in Casey Key
Discover more than 596 vacation rentals available in Casey 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 Casey Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Casey 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 Casey Key. On average, places to stay near Casey Key offer 860.66 ft², with nightly prices averaging CA $427.
With Casai, finding and comparing holiday rentals in Casey 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.
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Top Accommodation Types in Casey Key
| Type | Count |
|---|---|
| Vacation Homes | 405 |
| Holiday Apartments | 51 |
| Villas | 25 |
| Cottages | 16 |
Use these Quick Filters to Find a Holiday Rental in Casey Key
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Casey Key.
Weather in Casey Key, FL
View the weather forecast for Casey Key before booking your Casey Key Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Casey Key, FL
Casai offers a large selection of top attractions around Casey Key . Research things to do on your vacation before you visit Casey Key.
Frequently Asked Questions About Casey Key?
What are the top holiday rentals in Casey Key?
With numerous options available in Casey Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Casey Key:
- Addys Villas
- 1 Bedroom Duplex On Intracoastal W/Beach Access
- 2 BEDROOM ON INTRACOASTAL W/BEACH ACCESS
- Bayshore Beach House - Walk to Nokomis Beach! Close to Siesta Key, Venice Beach
- One Bedroom remodeled stand-alone Unit - steps from our private beach.
- Costal Heaven, Close to gulf, Close to shopping and restaurants.
- SHORE ACRES- Less than a mile to Nokomis Beach
- Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
- Tropical Oasis Estate on Casey Key - Large Pool, Private Dock, Steps to Beach
- Mid-century Waterfront Home with pool
How many holiday rentals have private pools in Casey Key?
Discover a selection of holiday rentals with private pools near Casey 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.
- Charming 2-beds house on the lake. Pool and large patio. Close to the beaches.
- 3 BR Pool Home In Nokomis - Close To Beaches
- Family beach home! Renovated waterfront home with pool, dock, and nearby beach
- 2 Bedroom/2 Bath Villa (Second Level) - Unit 6
Which holiday homes in Casey Key are best for families?
If you're searching for a family-friendly holiday home in Casey Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Casey Key:
- Beach Water Front Condo
- Waterfront retreat with kayaks, walk to the beach
- Escape Coastal Resort on Casey Key
How many Casai.ca holiday rentals are available in Casey Key?
As of 2026, Casai boasts over 596 properties listed in the Casey Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Casey Key.
People Also Ask
Finding the best prices in Casey Key
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