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Middleton Holiday Rentals

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Check prices for these dates

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

Our top choices for Middleton holiday 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 HK$600
HK$1,429 total
includes taxes & fees
3 Oct - 4 Oct
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 HK$353
HK$568 total
includes taxes & fees
22 Oct - 23 Oct
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 HK$741
HK$1,596 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$628
HK$829 total
includes taxes & fees
3 Oct - 4 Oct
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 HK$643
HK$2,448 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$600
HK$2,303 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$549
HK$745 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$777
HK$988 total
includes taxes & fees
9 Oct - 10 Oct
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 HK$953
HK$3,044 total
includes taxes & fees
16 Oct - 17 Oct
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 HK$612
HK$2,328 total
includes taxes & fees
3 Oct - 4 Oct
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 HK$883
HK$2,961 total
includes taxes & fees
9 Oct - 10 Oct
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 HK$628
HK$3,130 total
includes taxes & fees
8 Oct - 9 Oct
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 HK$883
HK$1,786 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$847
HK$2,950 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$706
HK$2,492 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$1,095
HK$2,270 total
includes taxes & fees
16 Oct - 17 Oct
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 HK$777
HK$2,085 total
includes taxes & fees
25 Oct - 26 Oct
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 HK$1,161
HK$2,937 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$588
HK$1,420 total
includes taxes & fees
4 Oct - 5 Oct
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 HK$699
HK$1,594 total
includes taxes & fees
8 Oct - 9 Oct
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

The Citrus on the Lake

The Citrus on the Lake

8/10 Good
"I’ve stayed here twice in the past couple of months and they never have any towels. That’s the only issue that I have. We were always being told that they were short on towels. Other than that, very nice laid-back atmosphere local bar scenes have a variety of live music options. TIKI WEST IS A MUST STOP AND EAT‼️"
Monica 2-night trip
Posted 2 hours ago
The Citrus on the Lake

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 holiday rental in Middleton?

Yes, there are holiday rentals close to the most popular sights in Middleton, or you can select a more secluded option if you're looking for a relaxing stay.

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

BETTER THAN A 5 STAR HOTEL WITH GOLF CART WHOLE HOUSE TOTALLY REMODELED: This holiday home rental outside of Middleton offers an outdoor pool, a patio and a BBQ 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 wider area, you’ll find Brownwood Paddock Square and Webster Westside Flea Market.

What’s a holiday rental in Middleton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleton. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.