Villa
10.0(81 Reviews)
5 Bedrooms
10 Guests
Private Pool
Parking
Pool
Ocean View
£950/Night
7 Nights - £6,648
Middlesex County Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Middlesex County
10.0
Villa
10.0(17 Reviews)
3 Bedrooms
8 Guests
Oceanfront
Breakfast- Parking
- Pool
£163/Night
7 Nights - £1,142
Villa
10.0(7 Reviews)
1 Bedroom
6 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£583/Night
7 Nights - £4,079
Villa
10.0(76 Reviews)
8 Bedrooms
20 Guests
- Private Pool
Hot Tub- Parking
- Pool
£899/Night
7 Nights - £6,294
House
10.0(14 Reviews)
4 Bedrooms
28 Guests
- Hot Tub
- Breakfast
- Parking
Balcony/Terrace
£220/Night
7 Nights - £1,539
Villa
10.0(34 Reviews)
5 Bedrooms
13 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
£822/Night
7 Nights - £5,757
Villa
10.0(33 Reviews)
20 Bedrooms
55 Guests
- Private Pool
- Breakfast
- Parking
- Pool
£2,657/Night
7 Nights - £18,601
Cottage
10.0(27 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Breakfast
- Parking
- Ocean View
£233/Night
7 Nights - £1,629
House
10.0(25 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Breakfast
£1,205/Night
7 Nights - £8,433
Luxury Holiday Rentals in Middlesex County
Over 4549+ Luxury Holiday Rentals in or Near Middlesex County
House
3 Bedrooms
10 Guests
- Parking
- Pool
- Balcony/Terrace
Air Conditioner
Unlock the Best Price
Unlock the Best Price
House
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
Unlock the Best Price
£7,359/Night
7 Nights - £51,515
£6,433/Night
7 Nights - £45,028
Villa
10.0(1 Review)
14 Bedrooms
30 Guests
- Oceanfront
- Hot Tub
- Breakfast
- Parking
£6,090/Night
7 Nights - £42,628
£5,954/Night
7 Nights - £41,681
New
House
5 Bedrooms
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£5,519/Night
7 Nights - £38,634
Villa
10 Bedrooms
20 Guests
- Air Conditioner
Internet
Child Friendly
Laundry
£5,344/Night
7 Nights - £37,407
Top-Rated Holiday Rentals with a Pool in Middlesex County
Over 2531+ The Best Private Villas and Holiday Rentals in Middlesex County with a Pool
Villa
10.0(23 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
£504/Night
7 Nights - £3,530
House
10.0(20 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
£213/Night
7 Nights - £1,488
Villa
10.0(15 Reviews)
4 Bedrooms
17 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
£1,578/Night
7 Nights - £11,049
£198/Night
7 Nights - £1,382
New
Apartment
10.0(13 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
Kitchen
£122/Night
7 Nights - £855
Villa
10.0(12 Reviews)
13 Bedrooms
26 Guests
- Private Pool
- Oceanfront
- Breakfast
- Parking
£2,608/Night
7 Nights - £18,257
House
10.0(11 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Ocean View
£330/Night
7 Nights - £2,307
New
House
10.0(9 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£1,966/Night
7 Nights - £13,765
Villa
10.0(8 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£582/Night
7 Nights - £4,076
Pet-Friendly Holiday Rentals in Middlesex County
Over 271+ Pet-Friendly Holiday Rentals in or Near Middlesex County
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
£68/Night
7 Nights - £479
House
10.0(2 Reviews)
2 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
View- Air Conditioner
£75/Night
7 Nights - £528
Cottage
10.0(1 Review)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Internet
£22/Night
7 Nights - £153
House
10.0(3 Reviews)
8 Bedrooms
16 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
£1,802/Night
7 Nights - £12,611
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Guests
- Parking
- Air Conditioner
- Internet
Pet Friendly
£64/Night
7 Nights - £449
£330/Night
7 Nights - £2,307
Villa
10.0(2 Reviews)
7 Bedrooms
14 Guests
- Breakfast
- Parking
- Pool
- Ocean View
£646/Night
7 Nights - £4,520
£465/Night
7 Nights - £3,259
House
10.0(2 Reviews)
3 Bedrooms
14 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
£184/Night
7 Nights - £1,290
Large Holiday Rentals and Private Villas in Middlesex County
Over 1416+ Large Holiday Rentals and Private Villas in or Near Middlesex County
Villa
10.0(8 Reviews)
5 Bedrooms
13 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
£562/Night
7 Nights - £3,937
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
Private Beach- Oceanfront
- Parking
- Pool
£240/Night
7 Nights - £1,683
Villa
10.0(2 Reviews)
1 Bedroom
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£192/Night
7 Nights - £1,342
Villa
10.0(7 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
£1,133/Night
7 Nights - £7,933
£120/Night
7 Nights - £840
House
10.0(6 Reviews)
8 Bedrooms
14 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
£625/Night
7 Nights - £4,376
Villa
10.0(6 Reviews)
4 Bedrooms
8 Guests
- Breakfast
- Parking
- Pool
- Ocean View
£342/Night
7 Nights - £2,392
Villa
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£319/Night
7 Nights - £2,236
Villa
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£106/Night
7 Nights - £743
Wheelchair Accessible Holiday Homes in Middlesex County
Over 203+ Wheelchair Accessible Holiday Homes in or Near Middlesex County
£170/Night
7 Nights - £1,192
Apartment
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
£98/Night
7 Nights - £687
House
8.0(4 Reviews)
1 Bedroom
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£82/Night
7 Nights - £571
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£76/Night
7 Nights - £535
£157/Night
7 Nights - £1,099
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£122/Night
7 Nights - £855
Apartment
10.0(4 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
£102/Night
7 Nights - £716
Apartment
10.0(3 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£86/Night
7 Nights - £604
Apartment
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
£83/Night
7 Nights - £579
Middlesex County Private Villas and Holiday Homes Under $200
Over 2488+ Middlesex County Private Villas and Holiday Homes Under $200
House
10.0(8 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£72/Night
7 Nights - £502
Apartment
10.0(6 Reviews)
1 Bedroom
2 Guests
- Private Beach
- Oceanfront
- Breakfast
- Parking
£80/Night
7 Nights - £556
Apartment
10.0(2 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Internet
£122/Night
7 Nights - £856
Apartment
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
£115/Night
7 Nights - £803
Bed & Breakfast
10.0(5 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£83/Night
7 Nights - £578
House
10.0(7 Reviews)
2 Bedrooms
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
£93/Night
7 Nights - £652
Condo
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
£101/Night
7 Nights - £709
Apartment
10.0(5 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
£130/Night
7 Nights - £912
House
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
£118/Night
7 Nights - £827
Instantly Bookable Holiday Homes in Middlesex County
Over 1689+ Instantly Bookable Holiday Homes in or Near Middlesex County
Condo
10.0(7 Reviews)
2 Bedrooms
5 Guests
- Breakfast
- Parking
- Pool
- Ocean View
£206/Night
7 Nights - £1,446
House
2 Bedrooms
2 Guests
£48/Night
7 Nights - £337
House
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
£233/Night
7 Nights - £1,633
Condo
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Breakfast
- Parking
- Ocean View
£154/Night
7 Nights - £1,074
House
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£151/Night
7 Nights - £1,059
House
10.0(4 Reviews)
3 Bedrooms
7 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£316/Night
7 Nights - £2,209
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Breakfast
- Parking
£242/Night
7 Nights - £1,695
House
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
£161/Night
7 Nights - £1,129
Apartment
10.0(4 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
£152/Night
7 Nights - £1,066
Book a Last Minute Place to Stay in Middlesex County
About Casai's Private Villas and Holiday Rentals in Middlesex County
Discover more than 4558 vacation rentals available in Middlesex County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middlesex County.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middlesex County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middlesex County. On average, places to stay near Middlesex County offer 1216.26 ft², with nightly prices averaging £460.
With Casai, finding and comparing holiday rentals in Middlesex County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Middlesex County, JM
There are 4558 Middlesex County, JM Holiday Rentals
- Prices for a holiday home in Middlesex County start at £14
- Top rated vacation home in Middlesex County is 5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler
- Most popular short term in Middlesex County is Ocean Coral Spring - All Inclusive
- Cheapest place to stay in Middlesex County is JamRock Casa
- Most expensive holiday rental in Middlesex County is 'One Love' Family Getaway w/pool 10mins Duns River
Frequently Asked Questions About Middlesex County?
What are the top holiday rentals in Middlesex County?
With numerous options available in Middlesex County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middlesex County:
- 5‑Bedroom Luxury Villa – Ocean View, Infinity Pool, Private Gym, Chef & Butler
- Luxury Private Oasis w/Stunning Ocean Views, Private Pool & Chef Option
- Siesta - Spacious Seaside villa, modern, spectacular location, pool, cook
- Serene, private retreat with magnificent views. 15-19 bedrooms, full staff
- Bahia - charming seaside cottage, wooden loft and shutters, garden, staff
- Gated, Four Bedroom, Four Bath, BEACH FRONT, SEA VIEW, Staffed
- Luxury Oceanfront Villa @ Chukka Cove, St Ann, private deck, sleeps upto 6, cook
- Leah's Retreat! 3-bedroom, house located 5 minutes from Ocho Rios attractions.
- Komfort Getaway Villa at Countrymist
- Sunspot Villa 4 BEDROOMS Runaway Bay, North Coast Beach
How many holiday rentals have private pools in Middlesex County?
Discover a selection of holiday rentals with private pools near Middlesex County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Middlesex County are best for families?
If you're searching for a family-friendly holiday home in Middlesex County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middlesex County:
How many Casai.uk holiday rentals are available in Middlesex County?
As of 2026, Casai boasts over 4558 properties listed in the Middlesex County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middlesex County.
Nearby Neighborhood (13)
| Neighborhood | Property Count |
|---|---|
| Caribbean Estates Vacation Rentals in Middlesex County, JM | 38 |
| Mammee Bay Estates Vacation Rentals in Middlesex County, JM | 512 |
| Bridgeport Vacation Rentals in Middlesex County, JM | 404 |
| River Oaks Vacation Rentals in Middlesex County, JM | 1302 |
| Spanish Town Zone Vacation Rentals in Middlesex County, JM | 138 |
| New Buckfield Vacation Rentals in Middlesex County, JM | 1151 |
| Great Pond Vacation Rentals in Middlesex County, JM | 1200 |
| Greenwich Estate Vacation Rentals in Middlesex County, JM | 525 |
| Caribbean Park Vacation Rentals in Middlesex County, JM | 484 |
| West Cumberland Vacation Rentals in Middlesex County, JM | 376 |
| Crystal Cove Vacation Rentals in Middlesex County, JM | 1258 |
| Horizon Park Vacation Rentals in Middlesex County, JM | 120 |
| Cave Hill Estate Vacation Rentals in Middlesex County, JM | 45 |
