Holiday rentals near The Villages Market Square
We found 1,600 holiday rentals — enter your dates for availability
Choose the right holiday rental within close proximity to The Villages Market Square. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as a fireplace and garden. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - The Villages Market Square
Showing deals for:15 Aug - 22 Aug
Image gallery for ⭐️POOL|GAMEROOM*Lanai Hangout*Open Concept Design🌊
9.09.0 out of 10 rating
Wonderful
(11 reviews)
⭐️POOL|GAMEROOM*Lanai Hangout*Open Concept Design🌊
Ocala, FL
7% off
Price is NZ$2,702
NZ$2,702
NZ$386 per night
includes taxes & fees
Image gallery for ***Great location-Mins from Brownwood! Brand New, Full-size House, Dogs Welcome!
9.89.8 out of 10 rating
Exceptional
(14 reviews)
***Great location-Mins from Brownwood! Brand New, Full-size House, Dogs Welcome!
Wildwood, FL
8% off
Price is NZ$2,914
NZ$2,914
NZ$416 per night
includes taxes & fees
Image gallery for Walking Distance To Spanish Springs.You'll Dance And Enjoy a healthy lifestyle.
1010 out of 10 rating
Exceptional
(7 reviews)
Walking Distance To Spanish Springs.You'll Dance And Enjoy a healthy lifestyle.
Lady Lake, FL
8% off
Price is NZ$4,354
NZ$4,354
NZ$622 per night
includes taxes & fees
Image gallery for Private Heated Pool and Hottub , Pet Friendly, New Golf Cart , Close to shopping
1010 out of 10 rating
Exceptional
(23 reviews)
Private Heated Pool and Hottub , Pet Friendly, New Golf Cart , Close to shopping
Lady Lake, FL
12% off
Price is NZ$4,929
NZ$4,929
NZ$704 per night
includes taxes & fees
Image gallery for Beautiful 2 Bedroom, 2 Bath House in Orange Blossoms
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Beautiful 2 Bedroom, 2 Bath House in Orange Blossoms
Lady Lake, FL
7% off
Price is NZ$1,794
NZ$1,794
NZ$256 per night
includes taxes & fees
Image gallery for Peyton's Patio Homes in The Villages, Florida
1010 out of 10 rating
Exceptional
(12 reviews)
Peyton's Patio Homes in The Villages, Florida
Lady Lake, FL
7% off
Price is NZ$1,984
NZ$1,984
NZ$283 per night
includes taxes & fees
Image gallery for Secluded Waterfront Retreat With Private Dock
9.89.8 out of 10 rating
Exceptional
(131 reviews)
Secluded Waterfront Retreat With Private Dock
Ocklawaha, FL
8% off
Price is NZ$5,251
NZ$5,251
NZ$750 per night
includes taxes & fees
Image gallery for Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL
1010 out of 10 rating
Exceptional
(15 reviews)
Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL
Wildwood, FL
6% off
Price is NZ$2,421
NZ$2,421
NZ$346 per night
includes taxes & fees
Image gallery for GREAT LOCATION BETWEEN SPANISH SPRINGS SQUARE & LAKE SUMTER LANDING
1010 out of 10 rating
Exceptional
(41 reviews)
GREAT LOCATION BETWEEN SPANISH SPRINGS SQUARE & LAKE SUMTER LANDING
Lady Lake, FL
7% off
Price is NZ$1,985
NZ$1,985
NZ$284 per night
includes taxes & fees
Image gallery for Private Heated Pool & Hottub - Pet Friendly- Close to L Sumpter & Spanish Spring
1010 out of 10 rating
Exceptional
(9 reviews)
Private Heated Pool & Hottub - Pet Friendly- Close to L Sumpter & Spanish Spring
The Villages, FL
12% off
Price is NZ$4,455
NZ$4,455
NZ$636 per night
includes taxes & fees
Image gallery for Historic Home Located Directly on Lake Harris
1010 out of 10 rating
Exceptional
(6 reviews)
Historic Home Located Directly on Lake Harris
Leesburg, FL
8% off
Price is NZ$8,729
NZ$8,729
NZ$1,247 per night
includes taxes & fees
Image gallery for Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.
1010 out of 10 rating
Exceptional
(58 reviews)
Perfect for FAMILY REUNIONS. Close by The Villages & shopping yet very private.
Lady Lake, FL
9% off
Price is NZ$7,135
NZ$7,135
NZ$1,019 per night
includes taxes & fees
Image gallery for Private Nature Oasis in The Villages FL
1010 out of 10 rating
Exceptional
(8 reviews)
Private Nature Oasis in The Villages FL
Okahumpka, FL
8% off
Price is NZ$3,627
NZ$3,627
NZ$518 per night
includes taxes & fees
Image gallery for Paradise Village home in perfect golfing and recreation center location.
1010 out of 10 rating
Exceptional
(27 reviews)
Paradise Village home in perfect golfing and recreation center location.
The Villages, FL
16% off
Price is NZ$1,623
NZ$1,623
NZ$232 per night
includes taxes & fees
Image gallery for Villages Retreat Includes Golf Cart with 2 Owner LifestyleIDs and 2 Guest Passes
1010 out of 10 rating
Exceptional
(24 reviews)
Villages Retreat Includes Golf Cart with 2 Owner LifestyleIDs and 2 Guest Passes
Lady Lake, FL
6% off
Price is NZ$1,701
NZ$1,701
NZ$243 per night
includes taxes & fees
Image gallery for Beautiful 2 Bed/2 Bath Ranch Available MAY 2025- DECEMBER 2025
1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful 2 Bed/2 Bath Ranch Available MAY 2025- DECEMBER 2025
The Villages, FL
7% off
Price is NZ$1,622
NZ$1,622
NZ$232 per night
includes taxes & fees
Image gallery for Stunning 3BR 2BA with heated pool and water view
1010 out of 10 rating
Exceptional
(57 reviews)
Stunning 3BR 2BA with heated pool and water view
Wildwood, FL
8% off
Price is NZ$3,608
NZ$3,608
NZ$515 per night
includes taxes & fees
Image gallery for WATERFRONT ESCAPE....LOVELY VIEWS AND IN TOWN
1010 out of 10 rating
Exceptional
(57 reviews)
WATERFRONT ESCAPE....LOVELY VIEWS AND IN TOWN
Leesburg, FL
12% off
Price is NZ$3,652
NZ$3,652
NZ$522 per night
includes taxes & fees
Image gallery for Lake Front, Pool Home with Boat Dock
1010 out of 10 rating
Exceptional
(18 reviews)
Lake Front, Pool Home with Boat Dock
Inverness, FL
8% off
Price is NZ$3,245
NZ$3,245
NZ$464 per night
includes taxes & fees
Image gallery for Casa Bohemian Retreat
1010 out of 10 rating
Exceptional
(19 reviews)
Casa Bohemian Retreat
Tavares, FL
8% off
Price is NZ$3,078
NZ$3,078
NZ$440 per night
includes taxes & fees
Image gallery for Spacious and beautiful house in Ocala Fl, 20 min from the club equestrian center
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious and beautiful house in Ocala Fl, 20 min from the club equestrian center
Ocala, FL
12% off
Price is NZ$3,430
NZ$3,430
NZ$490 per night
includes taxes & fees
Image gallery for Private Home Screened in Patio with Heated Pool Discount Week or Longer
9.69.6 out of 10 rating
Exceptional
(136 reviews)
Private Home Screened in Patio with Heated Pool Discount Week or Longer
Ocala, FL
6% off
Price is NZ$2,464
NZ$2,464
NZ$352 per night
includes taxes & fees
Image gallery for The Country Porch in Wildwood Florida - A stones throw away from The Villages!
1010 out of 10 rating
Exceptional
(57 reviews)
The Country Porch in Wildwood Florida - A stones throw away from The Villages!
Wildwood, FL
8% off
Price is NZ$2,407
NZ$2,407
NZ$344 per night
includes taxes & fees
Image gallery for FAMILY REUNIONS LOVE US. -5 miles to The Villages POOL HOT TUB SLEEPS UP TO 20
1010 out of 10 rating
Exceptional
(54 reviews)
FAMILY REUNIONS LOVE US. -5 miles to The Villages POOL HOT TUB SLEEPS UP TO 20
Weirsdale, FL
8% off
Price is NZ$9,144
NZ$9,144
NZ$1,306 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - The Villages Market Square
Villages Winter Sunset View Private Patio Villa, Golf Cart, Brownwood
Sleeps 5 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Charming 3-Bedroom, 2-Bath Rental in The Village of Collier w/Golf Cart & BBQ
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Quiet, Farm View, Extremely Clean and Comfortable Ranch home with Gas Golf Cart
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Stylish Home with Golf Cart, Lanai & Prime Location Near Town Squares!
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Beautiful 3/2 designer home, pet friendly, free WiFi, golf cart, hot tub
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
63 reviews(63 reviews)
Brand New Home to Share in The Villages- Bikes,Golf Clubs Available
Sleeps 1 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value