Condo
10.0(197 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Hot Tub
Parking
Pool
US $431/Night
7 Nights - US $3,014
Madeira Beach Winter Rentals & Holiday Homes
Discover winter rentals Madeira Beach - We found 1247 exact matches
- Up-front pricing
- No markup
- Trusted partners
Compare Winter Rental in Madeira Beach
10.0
US $409/Night
7 Nights - US $2,863
Condo
9.6(4 Reviews)
2 Bedrooms
6 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $375/Night
7 Nights - US $2,628
Condo
10.0(190 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $557/Night
7 Nights - US $3,896
US $378/Night
7 Nights - US $2,643
Condo
10.0(187 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $289/Night
7 Nights - US $2,023
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
Ocean View
US $1,377/Night
7 Nights - US $9,637
Apartment
10.0(127 Reviews)
1 Bedroom
3 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $382/Night
7 Nights - US $2,672
US $999/Night
7 Nights - US $6,993
Condo
10.0(122 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $232/Night
7 Nights - US $1,623
Apartment
10.0(1 Review)
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $492/Night
7 Nights - US $3,444
Condo
10.0(107 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $312/Night
7 Nights - US $2,183
Apartment
10.0(1 Review)
1 Bedroom
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $414/Night
7 Nights - US $2,898
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $410/Night
7 Nights - US $2,871
House
10.0(95 Reviews)
2 Bedrooms
4 Guests
- Parking
Balcony/Terrace
View
Kitchen
US $532/Night
7 Nights - US $3,721
Condo
10.0(92 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $436/Night
7 Nights - US $3,055
Apartment
10.0(92 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $266/Night
7 Nights - US $1,864
Apartment
10.0(64 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
US $336/Night
7 Nights - US $2,355
Condo
10.0(62 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $388/Night
7 Nights - US $2,716
Condo
10.0(48 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $323/Night
7 Nights - US $2,262
Condo
10.0(47 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $307/Night
7 Nights - US $2,147
Condo
10.0(45 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $472/Night
7 Nights - US $3,304
Condo
10.0(44 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $289/Night
7 Nights - US $2,025
Condo
10.0(43 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Spa
US $282/Night
7 Nights - US $1,971
About Madeira Beach Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 1247 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 Madeira Beach Winter Rentals
What are the top rated Winter Rentals in Madeira Beach?
There are a lot of options in Madeira Beach. If you plan on staying in the Madeira Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Madeira Beach:
- Gulf-Side Beach House - Tiki Bar · Direct Beach Access · No Roads to Cross
- Gulf Front Sunsets From the Balcony of This 3 BD/2 BA condo!
- Amazing Beachfront Condo 3BR/2BA - Spectacular View
- Sweeping views from this 3 bed/2bath condo
- Beautiful Beachfront Condo with Loads of Space
- Luxury Beach Escape near John's Pass - Seaview #403
- Coastal Getaway 3BR 3BA Condo with Pool Just 2 Blocks from the Beach
- Madeira Beach Waterfront Paradise
- Amazing Gulf Views at Seaview Condo Unit 304
- Madeira Beach 2BR/1.5B with Boat Slip
How much does it cost to rent a place to stay near Madeira Beach in the wintertime?
The average cost for winter rentals in Madeira Beach is $346 per night. Casai has a wide list of great winter places to stay near Madeira Beach that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Madeira Beach that allow pets?
Yes, here are the top cottage/chalet rentals in Madeira Beach that allow you to bring your pet or dog:
- REMODELED, immaculately designed, BEACHFRONT condo with gorgeous water views
- Arie Dam 301
- An Ocean Breeze puts a Mind at Ease
- Enjoy beautiful sunsets from the top floor in this 2 bed, 2 bath condo!
See all pet-friendly vacation rentals in Madeira Beach on Casai.com
Do you have any winter rentals in Madeira Beach that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Madeira Beach to find what works for you.
Are there winter accommodations in Madeira Beach that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 1247 private swimming pools or indoor pools accommodations near Madeira Beach along with other great amenities.
Do any winter holiday rentals in Madeira Beach have hot tubs?
About 1247 holiday rentals in Madeira Beach boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Madeira Beach?
Yes, there are many luxury places to stay in Madeira Beach for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Madeira Beach with all the best amenities for your next trip.
