Holiday rentals near Webster Westside Flea Market
We found holiday rentals — enter your dates for availability
Take a look at private holiday rentals close to Webster Westside Flea Market that can be your home away from home. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Webster Westside Flea Market
Showing deals for:1 Aug - 8 Aug
Image gallery for SWISS 41 - Golf Course
8.08.0 out of 10 rating
Very good
(10 reviews)
SWISS 41 - Golf Course
Clermont, FL
6% off
Price is NZ$4,451
NZ$4,451
NZ$636 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$2,863
NZ$2,863
NZ$409 per night
includes taxes & fees
Image gallery for SWISS 101 - Lake Olsen
8.48.4 out of 10 rating
Very good
(12 reviews)
SWISS 101 - Lake Olsen
Clermont, Florida
6% off
Price is NZ$4,022
NZ$4,022
NZ$575 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
(14 reviews)
Charming 3 Bedroom, 2 Bath Courtyard Villa in The Villages, FL
Wildwood, FL
6% off
Price is NZ$2,994
NZ$2,994
NZ$428 per night
includes taxes & fees
Image gallery for Citrus Blossom Cottage
1010 out of 10 rating
Exceptional
(17 reviews)
Citrus Blossom Cottage
Clermont, FL
6% off
Price is NZ$2,452
NZ$2,452
NZ$350 per night
includes taxes & fees
Image gallery for Enjoy your vacation in spacious private accommodation in Comfort Peace & Privacy
9.89.8 out of 10 rating
Exceptional
(117 reviews)
Enjoy your vacation in spacious private accommodation in Comfort Peace & Privacy
Groveland, FL
7% off
Price is NZ$2,054
NZ$2,054
NZ$293 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$1,594
NZ$1,594
NZ$228 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$8,575
NZ$8,575
NZ$1,225 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$3,563
NZ$3,563
NZ$509 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
8% off
Price is NZ$3,420
NZ$3,420
NZ$489 per night
includes taxes & fees
Image gallery for Dade City's Historic 1892 Locke Inn Estate
1010 out of 10 rating
Exceptional
(5 reviews)
Dade City's Historic 1892 Locke Inn Estate
Dade City, FL
15% off
Price is NZ$13,521
NZ$13,521
NZ$1,932 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$2,364
NZ$2,364
NZ$338 per night
includes taxes & fees
Image gallery for 'Cypress Lake House' in Floral City, Florida
9.89.8 out of 10 rating
Exceptional
(100 reviews)
'Cypress Lake House' in Floral City, Florida
Floral City, FL
6% off
Price is NZ$1,798
NZ$1,798
NZ$257 per night
includes taxes & fees
Image gallery for SWISS 28 - Lake Stephanie
9.69.6 out of 10 rating
Exceptional
(8 reviews)
SWISS 28 - Lake Stephanie
Clermont, FL
11% off
Price is NZ$4,198
NZ$4,198
NZ$600 per night
includes taxes & fees
Image gallery for Great Location! Pet Friendly!
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Great Location! Pet Friendly!
Wildwood, FL
7% off
Price is NZ$2,202
NZ$2,202
NZ$315 per night
includes taxes & fees
Image gallery for SWISS 61 - Lake Denise
8.48.4 out of 10 rating
Very good
(9 reviews)
SWISS 61 - Lake Denise
Clermont, Florida
6% off
Price is NZ$4,022
NZ$4,022
NZ$575 per night
includes taxes & fees
Image gallery for Luxury living minutes away from Brownwood Paddock Square, an ideal location.
1010 out of 10 rating
Exceptional
(18 reviews)
Luxury living minutes away from Brownwood Paddock Square, an ideal location.
Wildwood, FL
5% off
Price is NZ$1,887
NZ$1,887
NZ$270 per night
includes taxes & fees
Image gallery for King-Sized Comfort – 2 King Beds in a Serene "Hideaway" in The Villages
9.89.8 out of 10 rating
Exceptional
(11 reviews)
King-Sized Comfort – 2 King Beds in a Serene "Hideaway" in The Villages
Wildwood, FL
7% off
Price is NZ$2,190
NZ$2,190
NZ$313 per night
includes taxes & fees
Image gallery for SWISS 56 - Lake Denise
9.09.0 out of 10 rating
Wonderful
(15 reviews)
SWISS 56 - Lake Denise
Clermont, FL
6% off
Price is NZ$4,652
NZ$4,652
NZ$665 per night
includes taxes & fees
Image gallery for 45 minutes from Orlando & Parks a lot of nature park close by
9.29.2 out of 10 rating
Wonderful
(5 reviews)
45 minutes from Orlando & Parks a lot of nature park close by
Leesburg, FL
7% off
Price is NZ$2,001
NZ$2,001
NZ$286 per night
includes taxes & fees
Image gallery for April 2025 Available for Full or Partial Month Rental, discounted rate
1010 out of 10 rating
Exceptional
(61 reviews)
April 2025 Available for Full or Partial Month Rental, discounted rate
Wildwood, FL
8% off
Price is NZ$1,926
NZ$1,926
NZ$275 per night
includes taxes & fees
Image gallery for Amazing spacious Ranch! A country pearl.
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Amazing spacious Ranch! A country pearl.
Floral City, FL
24% off
Price is NZ$2,073
NZ$2,073
NZ$296 per night
includes taxes & fees
Image gallery for Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax
1010 out of 10 rating
Exceptional
(8 reviews)
Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax
Lake Panasoffkee, FL
9% off
Price is NZ$1,805
NZ$1,805
NZ$258 per night
includes taxes & fees
Image gallery for Gorgeous 3 bd-2 bth in Fenney w/4-seat Golf Cart; Near Brownwood, Sawgrass, Golf
1010 out of 10 rating
Exceptional
(5 reviews)
Gorgeous 3 bd-2 bth in Fenney w/4-seat Golf Cart; Near Brownwood, Sawgrass, Golf
Wildwood, FL
7% off
Price is NZ$2,522
NZ$2,522
NZ$360 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Webster Westside Flea Market
Private Resort Pool Home
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
SWISS 53-Lake Denise
Sleeps 6 · 3 bedrooms · 2 bathrooms
BEAUTIFUL RETREAT HOME ON 2 FENCED PRIVATE ACRES. WALK TO FOREST AND GOLF!
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
48 reviews(48 reviews)
Private Lake View House Rental close to wonderful Big Bass Grill restaurant
Sleeps 8 · 3 bedrooms · 2+ bathrooms
8.08.0 out of 10
Very goodvery good
2 reviews(2 reviews)
SWISS 65 - Lake Denise
Sleeps 6 · 3 bedrooms · 3 bathrooms
6.06.0 out of 10
2 reviews(2 reviews)
Withlacoochee River House on the main channel w/ kayaks, bikes, canoes
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Top rated rentals - Webster Westside Flea Market
First time staying in the Villages
1010 out of 10
Exceptionalexceptional
50 reviews(50 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