House
10.0(158 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Hot Tub
Pool
Ocean View
CA $636/Night
7 Nights - CA $4,451
Captiva Winter Rentals & Holiday Homes
Discover winter rentals Captiva - We found 657 exact matches
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Compare Winter Rental in Captiva
10.0
House
10.0(2 Reviews)
3 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
Breakfast
Parking
CA $1,031/Night
7 Nights - CA $7,214
CA $532/Night
7 Nights - CA $3,723
House
10.0(90 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Parking
- Pool
CA $792/Night
7 Nights - CA $5,546
House
10.0(1 Review)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Pool
Spa
CA $1,593/Night
7 Nights - CA $11,151
House
10.0(68 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Pool
- Ocean View
Balcony/Terrace
CA $672/Night
7 Nights - CA $4,702
House
10.0(1 Review)
4 Bedrooms
10 Guests
Private Beach- Oceanfront
- Hot Tub
- Breakfast
CA $989/Night
7 Nights - CA $6,926
House
10.0(68 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $606/Night
7 Nights - CA $4,242
House
9.6(6 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
View
CA $521/Night
7 Nights - CA $3,650
House
10.0(66 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $605/Night
7 Nights - CA $4,234
House
9.5(2 Reviews)
4 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,544/Night
7 Nights - CA $10,808
House
10.0(53 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $705/Night
7 Nights - CA $4,932
Apartment
8.9(12 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $441/Night
7 Nights - CA $3,084
Condo
10.0(46 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $857/Night
7 Nights - CA $5,998
House
10.0(35 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $1,037/Night
7 Nights - CA $7,257
House
10.0(34 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $884/Night
7 Nights - CA $6,188
House
10.0(32 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
CA $568/Night
7 Nights - CA $3,976
House
10.0(15 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $790/Night
7 Nights - CA $5,532
Villa
10.0(10 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $327/Night
7 Nights - CA $2,285
House
10.0(9 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $1,072/Night
7 Nights - CA $7,506
Apartment
10.0(9 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $367/Night
7 Nights - CA $2,569
House
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $728/Night
7 Nights - CA $5,098
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $323/Night
7 Nights - CA $2,261
Condo
10.0(3 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $429/Night
7 Nights - CA $3,001
About Captiva Winter Rental on Casai.ca
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 657 accommodations for your upcoming winter getaway, whether you're dreaming of azure waters and sun-kissed beaches or charming coastal towns.
At Casai, we present a diverse array of listings for holiday homes and villas nestled in the picturesque landscapes of the Mediterranean and the Caribbean. From luxurious villas overlooking crystal-clear waters to charming holiday homes nestled amidst palm-fringed shores, our curated selection caters to every preference and ensures an unforgettable retreat.
Indulge in the epitome of luxury with our Mediterranean and Caribbean villas, boasting opulent amenities such as private pools, spacious outdoor terraces, serene gardens, and breathtaking ocean views. Whether you're seeking a romantic escape, a family adventure, or a group getaway, our listings offer the perfect blend of comfort and sophistication.
Escape the winter chill and bask in the warmth of the Mediterranean or Caribbean sun. Explore our collection of holiday homes and villas, meticulously curated to provide the ultimate sanctuary for your winter retreat. With Casai, your dream vacation awaits.
Winter Rental: Explore Top Destinations
Frequently Asked Questions About Captiva Winter Rentals
What are the top rated Winter Rentals in Captiva?
There are a lot of options in Captiva. If you plan on staying in the Captiva area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Captiva:
- 1 Min to Beach, New Luxury pool home, Gulf sunrise and sunsets, club option
- "Laika Lane Gem! Private Pool Home, 3 Min to Beach – Family Friendly Fun!"
- Perfect Village location, FREE golf cart and bicycles. New price, All 5 stars !
- 5-bedroom vacation home in the Village with just a short walk to Captiva Beach!
- Captiva's Finest Multi-Generation Consistent 5-Star Vacation Home!
- Bluefin Beach House
- Manatee Haven: Screened Pool, Spa, Elevator
- Island Oasis/Hidden Beach House-Private pool
- It's A Colorful Cupcake World On Captiva Island
- Rum Cove 4BR Waterfront North Captiva Home with Pool & Golf Cart
How much does it cost to rent a place to stay near Captiva in the wintertime?
The average cost for winter rentals in Captiva is $952 per night. Casai has a wide list of great winter places to stay near Captiva that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Captiva that allow pets?
Yes, here are the top cottage/chalet rentals in Captiva that allow you to bring your pet or dog:
- Rockstar Beach House North Captiva Island, 25’ boat slip, NCIC pools, golf cart
- Island Retreat: Your Exclusive Oasis Awaits
- Tween Waters Island Resort & Spa
- Captiva Mermaid Pool House - Beachside of Village Center
See all pet-friendly vacation rentals in Captiva on Casai.ca
Do you have any winter rentals in Captiva that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Captiva to find what works for you.
Are there winter accommodations in Captiva that have indoor swimming pools?
As of 2026, the data from Casai.ca shows that there are over 657 private swimming pools or indoor pools accommodations near Captiva along with other great amenities.
Do any winter holiday rentals in Captiva have hot tubs?
About 657 holiday rentals in Captiva boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Captiva?
Yes, there are many luxury places to stay in Captiva for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Captiva with all the best amenities for your next trip.
