Condo
10.0(242 Reviews)
1 Bedroom
4 Guests
Parking
Pool
Ocean View
Balcony/Terrace
US $244/Night
7 Nights - US $1,706
Stuart Winter Rentals & Holiday Homes
Discover winter rentals Stuart - We found 344 exact matches
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Compare Winter Rental in Stuart
10.0
House
10.0(4 Reviews)
1 Bedroom
2 Guests
Hot Tub- Parking
Spa
Internet
US $312/Night
7 Nights - US $2,184
US $195/Night
7 Nights - US $1,365
House
10.0(86 Reviews)
1 Bedroom
2 Guests
Private Pool- Hot Tub
- Parking
- Pool
US $270/Night
7 Nights - US $1,892
US $1,325/Night
7 Nights - US $9,275
Condo
10.0(78 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $722/Night
7 Nights - US $5,057
Villa
10.0(1 Review)
8 Bedrooms
20 Guests
Private Beach
Oceanfront- Hot Tub
Breakfast
US $1,583/Night
7 Nights - US $11,081
Cottage
10.0(62 Reviews)
1 Bedroom
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $261/Night
7 Nights - US $1,827
House
10.0(1 Review)
8 Bedrooms
20 Guests
- Private Pool
- Private Beach
- Oceanfront
- Hot Tub
US $1,400/Night
7 Nights - US $9,800
Bed & Breakfast
10.0(55 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Breakfast
- Parking
- Pool
US $194/Night
7 Nights - US $1,361
House
10.0(1 Review)
8 Bedrooms
19 Guests
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $1,312/Night
7 Nights - US $9,184
Condo
10.0(53 Reviews)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $280/Night
7 Nights - US $1,962
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Spa
- Ocean View
US $213/Night
7 Nights - US $1,489
Condo
10.0(52 Reviews)
2 Bedrooms
5 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $444/Night
7 Nights - US $3,108
Cottage
10.0(38 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $283/Night
7 Nights - US $1,981
House
10.0(29 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $309/Night
7 Nights - US $2,164
Cottage
10.0(24 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $203/Night
7 Nights - US $1,418
Condo
10.0(18 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $293/Night
7 Nights - US $2,054
Condo
10.0(18 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- View
US $127/Night
7 Nights - US $890
Apartment
10.0(13 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $216/Night
7 Nights - US $1,510
Condo
10.0(12 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $189/Night
7 Nights - US $1,324
New
Cottage
10.0(11 Reviews)
1 Bedroom
2 Guests
- Parking
Kitchen
Air Conditioner- Internet
US $168/Night
7 Nights - US $1,176
Condo
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $104/Night
7 Nights - US $728
House
10.0(9 Reviews)
2 Bedrooms
4 Guests
- Kitchen
- Air Conditioner
- Internet
Pet Friendly
US $311/Night
7 Nights - US $2,177
About Stuart Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 344 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 Stuart Winter Rentals
What are the top rated Winter Rentals in Stuart?
There are a lot of options in Stuart. If you plan on staying in the Stuart area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Stuart:
- "Carpe Diem":ON the Beach w/heated Pool/hottub & dock.See the Video! DISCOUNTS!
- Eden Beach! Ocean-to-River Fla Beach House. ON THE BEACH! Dock, hot tub, & more
- Art on the Beach: Ocean-to-river house, ON beach. Pool, Hot Tub, Elevator, Dock
- Heaven Can't Wait: ON the BEACH! Heated pool + hot tub, private dock. 7BR/5BA
- Del Mar al Cielo: Luxury Beachfront Estate ON the Beach! w/elevator+pool!
- Tropical Resort Style Retreat w/Pool House 4BR, 3 Bath
- Aquatopia South: Riverfront Beach House, Steps 2 Ocean. Heated Pool & Dock!
- Stuart Splash Pool Home; near Downtown Stuart & Hutchinson Island Beaches 🏖
- Avalon: 8BR/5BA Ocean-to-River Palace; Heated pool, hot tub, private dock, more!
- Aquarius South: Luxe 10BR/6BA , w/heated swimming pool+spa, private dock & more
How much does it cost to rent a place to stay near Stuart in the wintertime?
The average cost for winter rentals in Stuart is $490 per night. Casai has a wide list of great winter places to stay near Stuart that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Stuart that allow pets?
Yes, here are the top cottage/chalet rentals in Stuart that allow you to bring your pet or dog:
- "Ocean Oasis" amazing views from direct beachfront condo on Hutchinson Island
- Waterfront Stuart Oasis w/Hot Tub & Dock!
- Old Colorado Inn
- Private Oceanfront Condo at Hutchinson Island Marriott Resort
See all pet-friendly vacation rentals in Stuart on Casai.com
Do you have any winter rentals in Stuart that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Stuart to find what works for you.
Are there winter accommodations in Stuart that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 344 private swimming pools or indoor pools accommodations near Stuart along with other great amenities.
Do any winter holiday rentals in Stuart have hot tubs?
About 344 holiday rentals in Stuart boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Stuart?
Yes, there are many luxury places to stay in Stuart for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Stuart with all the best amenities for your next trip.
