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Middleton Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middleton vacation rentals

A wooden console table with a fireplace, a decorative vase, and various items on top.

1. Cozy Pink Vintage Studio with Private Fenced Yard

Cozy Pink Vintage Studio with Private Fenced Yard
Coleman
9.6 out of 10, Exceptional, (8 reviews)
"The host went out of her way to make sure we had everything we needed."
United States
Cynthia B.
The price is ￥12,039
￥28,659 total
includes taxes & fees
Oct 3 - Oct 4
Cozy Pink Vintage Studio with Private Fenced Yard
A single-story house with a front yard, a sidewalk, and a large tree with hanging moss.

2. old Florida cottage canal front

old Florida cottage canal front
Lake Panasoffkee
8.8 out of 10, Excellent, (8 reviews)
"Host was responsive and friendly. Place is great. Neighbors are wonderful. "
United States
Jeremy A.
The price is ￥6,373
￥10,641 total
includes taxes & fees
Oct 14 - Oct 15
old Florida cottage canal front
A kitchen with a black metal table and chairs, a white vase with green plants, and a window with blinds.

3. Vintage Charm on Peaceful Mini Farm - Pet Friendly

Vintage Charm on Peaceful Mini Farm - Pet Friendly
Coleman
10.0 out of 10, Exceptional, (27 reviews)
"Very clean and comfortable bed."
United States
Cheryl D.
The price is ￥14,871
￥32,319 total
includes taxes & fees
Oct 7 - Oct 8
Vintage Charm on Peaceful Mini Farm - Pet Friendly
A modern living space with a sofa, a dining table, a kitchen area, and a flat-screen TV mounted on the wall.

4. Brand New! Modern Guesthouse!

Brand New! Modern Guesthouse!
Lake Panasoffkee
8.0 out of 10, Very good, (1 review)
"This is a cute place in a quiet neighborhood. Just what we needed, a quiet place to stay while visiting family in the area. Very basic kitchen and dining needs. Enough to make easy meals to enjoy while there. It is NOT a five star hotel but we very much enjoyed this cute little place."
United States
Karen G.
The price is ￥12,590
￥16,619 total
includes taxes & fees
Oct 7 - Oct 8
Brand New! Modern Guesthouse!
A kitchen with white cabinets, a microwave, and a sink. There are wicker chairs at the island.

5. Brand New Designer Home!- 5 minutes from East Port

Brand New Designer Home!- 5 minutes from East Port
Sumterville
9.8 out of 10, Exceptional, (6 reviews)
"Loved our stay.. Nicely appointed, every thing you need. Wish we could have stayed longer."
United States
denise K.
The price is ￥13,382
￥49,622 total
includes taxes & fees
Oct 5 - Oct 6
Brand New Designer Home!- 5 minutes from East Port
Two wicker chairs with red cushions on a wooden deck.

6. Cozy Home w/ Game Room Villages and Lake Harris

Cozy Home w/ Game Room Villages and Lake Harris
Leesburg
8.8 out of 10, Excellent, (15 reviews)
"Amazing stay!"
United States
Dennis
The price is ￥12,043
￥46,208 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Home w/ Game Room Villages and Lake Harris
A compact RV kitchen with a double sink, wooden cabinets, a window, and a small countertop area.

7. RV camper in a peaceful place

RV camper in a peaceful place
Lake Panasoffkee
10.0 out of 10, Exceptional, (2 reviews)
"From pre-reservation questions, to check-in to check-out, Julia was very responsive. The property was just what we needed for our weekend. Quiet, quaint and all the basics were provided. Thank you!"
United States
Kevin B.
The price is ￥11,016
￥14,935 total
includes taxes & fees
Oct 7 - Oct 8
RV camper in a peaceful place
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a flat-screen TV mounted on the wall.

8. Newly renovated vacation house!

Newly renovated vacation house!
Lake Panasoffkee
10.0 out of 10, Exceptional, (6 reviews)
"Awesome place"
United States
Michelle S.
The price is ￥15,586
￥19,826 total
includes taxes & fees
Oct 2 - Oct 3
Newly renovated vacation house!
A modern kitchen with stainless steel appliances, dark cabinetry, and a marble countertop.

9. Charming 2-bedroom house in The Villages with Golf Cart

Charming 2-bedroom house in The Villages with Golf Cart
The Villages
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place. It was very clean and convenient for my family The rooms were very comfortable and were able to enjoy our time in Florida."
United States
Kevin
The price is ￥19,120
￥61,375 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2-bedroom house in The Villages with Golf Cart
A living room with two sofas, a coffee table, and a rug.

10. 5 minutes to EastPort, Life Style ID's!

5 minutes to EastPort, Life Style ID's!
Sumterville
The price is ￥12,275
￥46,693 total
includes taxes & fees
Oct 27 - Oct 28
5 minutes to EastPort, Life Style ID's!
A living room with a ceiling fan, a coffee table, sofas, and a dining area with a table and chairs.

11. Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square

Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square
Collier
10.0 out of 10, Exceptional, (3 reviews)
"This was one of the most well-organized stays we have ever had through Vrbo! Everything was documented and labeled extremely well (keys, passwords, check-in and out, etc.). The house itself was fabulous, clean, comfy beds, SOFT towels, beautifully decorated. Everything we needed was provided, from cookware to the grill to beach towels to the golf cart. Highly recommended! Would definitely stay again!"
United States
KENDRA W.
The price is ￥17,711
￥59,726 total
includes taxes & fees
Oct 2 - Oct 3
Beautiful 2/2 Patio Villa w/cart in Village of Collier close to Brownwood Square
A modern kitchen with a central island, a dining table with chairs, and a chandelier.

12. Lakefront Retreat • Patio + Grill • Pet Friendly

Lakefront Retreat • Patio + Grill • Pet Friendly
Leesburg
2.0 out of 10, (1 review)
The price is ￥12,594
￥62,794 total
includes taxes & fees
Oct 6 - Oct 7
Lakefront Retreat • Patio + Grill • Pet Friendly
A sign for 'Big Bass' with a parrot and a fish, indicating a waterfront resort.

13. Cabin on lake panasoffkee, near top spot big bass grill

Cabin on lake panasoffkee, near top spot big bass grill
Lake Panasoffkee
8.0 out of 10, Very good, (2 reviews)
"The cabin was so cute and cleanThe only thing I wish there was a microwave. No big deal. I heated my stuff on the stove "
United States
Mary B.
The price is ￥17,704
￥35,822 total
includes taxes & fees
Oct 7 - Oct 8
Cabin on lake panasoffkee, near top spot big bass grill
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

14. Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
Collier
10.0 out of 10, Exceptional, (2 reviews)
"Kelly makes her home very welcoming and is beautiful for family get togethers or just sitting quietly on the back patio.Beds kitchen and essentials were perfect Thank you Kelly for sharing your home"
United States
Rebecca B.
The price is ￥16,996
￥59,955 total
includes taxes & fees
Oct 5 - Oct 6
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A sunlit room with wicker furniture, a glass table, and large windows.

15. Golf Cart Included, In the Heart of The Villages

Golf Cart Included, In the Heart of The Villages
Fernandina
8.8 out of 10, Excellent, (3 reviews)
"We very much enjoyed this home. Comfortable and a great location! We will definitely book this home again!"
United States
Susan H.
The price is ￥14,163
￥49,973 total
includes taxes & fees
Oct 4 - Oct 5
Golf Cart Included, In the Heart of The Villages
A modern kitchen with a central island, white cabinets, and pendant lighting.

16. Boutique Mid-Century Home by Villages Fenced Yard

Boutique Mid-Century Home by Villages Fenced Yard
Coleman
9.8 out of 10, Exceptional, (9 reviews)
"Lovely and clean home. I would 100% stay here again. "
United States
Morgan M.
The price is ￥21,953
￥45,680 total
includes taxes & fees
Oct 11 - Oct 12
Boutique Mid-Century Home by Villages Fenced Yard
A modern kitchen with white cabinetry, a central island, and a dining area with a table and chairs.

17. BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
Alhambra
10.0 out of 10, Exceptional, (38 reviews)
"Excellent property and lovely stay and host!"
United States
Pamela L.
The price is ￥15,586
￥41,826 total
includes taxes & fees
Oct 24 - Oct 25
BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED
A modern outdoor seating area with a wicker sectional sofa, a wooden coffee table, and a large umbrella.

18. Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
3.0 star property
Collier
The price is ￥23,291
￥58,910 total
includes taxes & fees
Oct 4 - Oct 5
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
A swimming pool with a hot tub, surrounded by a brick patio, and a house with a balcony.

19. Guest House with pool, boat parking

Guest House with pool, boat parking
Leesburg
8.8 out of 10, Excellent, (29 reviews)
"The host was right on top of things when we needed something. The little pool was great for winding down in the evening. There were a couple things that I think could improve the rental: The large fridge did not work, but luckily the small one took care of that. Other issues were pretty minor.We would stay here again.Wes"
United States
Wes C.
The price is ￥11,807
￥28,487 total
includes taxes & fees
Oct 4 - Oct 5
Guest House with pool, boat parking
A covered outdoor area with a view of a pond and surrounding greenery.

20. Waterfront Cottage on Haynes Creek

Waterfront Cottage on Haynes Creek
Leesburg
9.4 out of 10, Exceptional, (18 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
The price is ￥14,027
￥31,982 total
includes taxes & fees
Oct 3 - Oct 4
Waterfront Cottage on Haynes Creek
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middleton Hotel Reviews

Hampton Inn & Suites Lady Lake/The Villages

Hampton Inn & Suites Lady Lake/The Villages

10/10 Excellent
"All staff were professional...caring and helpful"
Louis 4-night trip
Posted less than an hour ago
Hampton Inn & Suites Lady Lake/The Villages

Find out more about Middleton

Search for holiday rentals in Middleton on Expedia! You can easily find your home rentals, villas, holiday apartments in Middleton using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middleton!

Frequently asked questions

Can I find a vacation rental in Middleton?

Yes, there are vacation rentals close to well known sights in Middleton, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Middleton has to offer?

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED: This vacation home rental near Middleton offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Middleton?

Explore the area and family-friendly sights such as The Florida International Teaching Zoo, or get out into nature at a spot like Venetian Gardens. In the larger area, you’ll find Brownwood Paddock Square and Webster Westside Flea Market.

What’s a vacation rental in Middleton like?

A vacation rental is a private property you can book for a few weeks or just a few days in Middleton. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family getaway.