Condo
10.0(33 Reviews)
2 Bedrooms
6 Guests
Private Pool
Oceanfront
Hot Tub
Parking
US $373/Night
7 Nights - US $2,610
Estero Winter Rentals & Holiday Homes
Discover winter rentals Estero - We found 226 exact matches
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Compare Winter Rental in Estero
10.0
House
9.7(3 Reviews)
1 Bedroom
4 Guests
- Parking
Balcony/Terrace
View
Air Conditioner
US $167/Night
7 Nights - US $1,172
US $133/Night
7 Nights - US $929
Cottage
10.0(22 Reviews)
1 Bedroom
4 Guests
- Parking
Kitchen- Air Conditioner
Internet
US $236/Night
7 Nights - US $1,654
New
House
5 Bedrooms
10 Guests
- Hot Tub
- Parking
Pool- Balcony/Terrace
US $1,033/Night
7 Nights - US $7,228
Condo
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $281/Night
7 Nights - US $1,970
US $127/Night
7 Nights - US $887
Condo
10.0(11 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $215/Night
7 Nights - US $1,508
Hotel
8.7(64 Reviews)
EV Charge Station- Parking
- Pool
- Balcony/Terrace
US $151/Night
7 Nights - US $1,054
House
10.0(6 Reviews)
2 Bedrooms
5 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $206/Night
7 Nights - US $1,443
US $304/Night
7 Nights - US $2,125
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $158/Night
7 Nights - US $1,108
Condo
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $252/Night
7 Nights - US $1,767
House
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $158/Night
7 Nights - US $1,106
House
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $368/Night
7 Nights - US $2,577
Villa
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
Ocean View
US $161/Night
7 Nights - US $1,125
Villa
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
Spa
US $487/Night
7 Nights - US $3,408
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $209/Night
7 Nights - US $1,464
Condo
10.0(1 Review)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $188/Night
7 Nights - US $1,313
Condo
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $168/Night
7 Nights - US $1,173
Villa
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $140/Night
7 Nights - US $979
Condo
9.8(10 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $154/Night
7 Nights - US $1,077
Condo
9.2(10 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $138/Night
7 Nights - US $965
Condo
9.0(2 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Spa
- Balcony/Terrace
US $560/Night
7 Nights - US $3,919
About Estero Winter Rental on Casai.com
Craving a winter escape in the enchanting locales of the Mediterranean or the Caribbean? Explore 226 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 Estero Winter Rentals
What are the top rated Winter Rentals in Estero?
There are a lot of options in Estero. If you plan on staying in the Estero area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Estero:
- Beautiful updated pool home in a quiet, gated community.
- Newly remodeled 3-bedroom condo in a bundled community
- Country Creek -Lovely updated 3 bed/2 bath Estero home with hot tub and golf
- Fabulous home w/new pool & spa. Minutes to golf, shop, dine, and fun-in-sun.
- 3 BR, 2 Bath W/Community Pool & Exercise Rm Located In A Quiet Gated Community
- Gated Community Executive Home with Pool and Hot Tub! Private Golf, Tennis CC
- Relaxing Townhome in Bella Terra Community
- Bella Terra - Top floor condo with Lake Views!
- Family-Friendly Pool Home
- 4 bedroom/3 bedroom pool home at The Preserve at Corkscrew
How much does it cost to rent a place to stay near Estero in the wintertime?
The average cost for winter rentals in Estero is $286 per night. Casai has a wide list of great winter places to stay near Estero that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Are there any winter cottages/chalets in Estero that allow pets?
Yes, here are the top cottage/chalet rentals in Estero that allow you to bring your pet or dog:
- BEAUTIFULLY FURNISHED AND DECORATED CONDO IN STONEYBROOK GATED GOLF COMMUNITY
- Zen Container Tiny Home with Fenced-in Yard, Fire Pit, Centrally located and Pet Friendly
- Embassy Suites by Hilton Fort Myers Estero
- River Ranch Oaks
See all pet-friendly vacation rentals in Estero on Casai.com
Do you have any winter rentals in Estero that are suitable for families?
Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Estero to find what works for you.
Are there winter accommodations in Estero that have indoor swimming pools?
As of 2026, the data from Casai.com shows that there are over 226 private swimming pools or indoor pools accommodations near Estero along with other great amenities.
Do any winter holiday rentals in Estero have hot tubs?
About 226 holiday rentals in Estero boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:
Are there luxury winter rentals in Estero?
Yes, there are many luxury places to stay in Estero for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Estero with all the best amenities for your next trip.
