Downtown Holiday Rentals
Boat Rental
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
8 Guests
Fireplace/Heating
Pool
Balcony/Terrace
Pet Friendly
£310/Night
7 Nights - £2,172
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pool
View
Breakfast
Parking
£707/Night
7 Nights - £4,948
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Balcony/Terrace
- Parking
Internet
Child Friendly
£1,324/Night
7 Nights - £9,269
New
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
Air Conditioner- Internet
- Child Friendly
£709/Night
7 Nights - £4,963
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
1496.18 ft²
- Pool
- View
- Breakfast
- Parking
£661/Night
7 Nights - £4,624
House
4 Bedrooms
3 Baths
10 Guests
3500 ft²
Private Pool
Oceanfront
Hot Tub- Fireplace/Heating
£443/Night
7 Nights - £3,101
New
House
3 Bedrooms
2 Baths
6 Guests
1060 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
Kitchen
£167/Night
7 Nights - £1,171
New
Resort
2 Baths
6 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Air Conditioner
£575/Night
7 Nights - £4,028
New
Resort
2 Baths
6 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
£334/Night
7 Nights - £2,336
Luxury Holiday Rentals in Downtown
Over 1507+ Luxury Holiday Rentals in or Near Downtown
House
9.5Exceptional
(2 Reviews)
6 Bedrooms
6 Baths
24 Guests
2400.35 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£4,450/Night
7 Nights - £31,151
House
1 Bedroom
10 Baths
20 Guests
3702.79 ft²
Spa- Pool
- Pet Friendly
- Parking
£4,222/Night
7 Nights - £29,552
House
1 Bedroom
7 Baths
12 Guests
4004.17 ft²
- Pool
- View
- Pet Friendly
- Parking
£3,845/Night
7 Nights - £26,916
House
8 Bedrooms
9 Baths
20 Guests
5005.22 ft²
- Pool
- Pet Friendly
- Parking
- Air Conditioner
£3,734/Night
7 Nights - £26,140
House
8 Bedrooms
9 Baths
16 Guests
4004.17 ft²
- Pool
- View
- Pet Friendly
- Parking
£3,558/Night
7 Nights - £24,904
House
8 Bedrooms
9 Baths
18 Guests
3778.13 ft²
- Pool
- View
- Pet Friendly
- Parking
£3,183/Night
7 Nights - £22,281
House
10.0Exceptional
(5 Reviews)
16 Bedrooms
14 Baths
32 Guests
5200 ft²
- Private Pool
- Oceanfront
- Pool
Ocean View
£3,142/Night
7 Nights - £21,994
Apartment
4 Bedrooms
4 Baths
12 Guests
1603.82 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£3,035/Night
7 Nights - £21,248
House
13 Bedrooms
15 Baths
32 Guests
5198.97 ft²
- Spa
- Pool
- Pet Friendly
- Parking
£2,883/Night
7 Nights - £20,179
Top-Rated Holiday Rentals with a Pool in Downtown
Over 1124+ The Best Private Villas and Holiday Rentals in Downtown with a Pool
House
10.0Exceptional
(410 Reviews)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£468/Night
7 Nights - £3,279
House
10.0Exceptional
(247 Reviews)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£468/Night
7 Nights - £3,279
Cottage
10.0Exceptional
(237 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£633/Night
7 Nights - £4,432
House
10.0Exceptional
(217 Reviews)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£534/Night
7 Nights - £3,741
House
10.0Exceptional
(214 Reviews)
3 Bedrooms
3 Baths
8 Guests
1500 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£486/Night
7 Nights - £3,400
House
10.0Exceptional
(207 Reviews)
3 Bedrooms
3 Baths
8 Guests
1875 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£1,469/Night
7 Nights - £10,284
House
10.0Exceptional
(206 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
£361/Night
7 Nights - £2,525
House
10.0Exceptional
(193 Reviews)
3 Bedrooms
3 Baths
7 Guests
1855 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
£1,206/Night
7 Nights - £8,444
Condo
10.0Exceptional
(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
£411/Night
7 Nights - £2,878
Pet-Friendly Holiday Rentals in Downtown
Over 441+ Pet-Friendly Holiday Rentals in or Near Downtown
Apartment
10.0Exceptional
(96 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
£265/Night
7 Nights - £1,855
House
10.0Exceptional
(2 Reviews)
6 Bedrooms
7 Baths
14 Guests
2895.49 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
£2,201/Night
7 Nights - £15,409
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Pet Friendly
- Parking
- Internet
£544/Night
7 Nights - £3,809
House
10.0Exceptional
(22 Reviews)
2 Bedrooms
1 Bath
4 Guests
810 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£144/Night
7 Nights - £1,011
House
10.0Exceptional
(1 Review)
6 Bedrooms
7 Baths
14 Guests
2895.49 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
£2,720/Night
7 Nights - £19,039
House
10.0Exceptional
(15 Reviews)
2 Bedrooms
3 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£298/Night
7 Nights - £2,083
House
10.0Exceptional
(14 Reviews)
1 Bedroom
2 Baths
4 Guests
850 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
£516/Night
7 Nights - £3,610
House
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
£190/Night
7 Nights - £1,330
House
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
6 Guests
810 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£129/Night
7 Nights - £905
Large Holiday Rentals and Private Villas in Downtown
Over 150+ Large Holiday Rentals and Private Villas in or Near Downtown
Villa
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
£579/Night
7 Nights - £4,052
House
10.0Exceptional
(1 Review)
6 Bedrooms
7 Baths
14 Guests
2895.49 ft²
- Fireplace/Heating
- Pool
- View
- Pet Friendly
£2,233/Night
7 Nights - £15,632
Villa
7.4Very Good
(3 Reviews)
1 Bedroom
1 Bath
- Pool
- Ocean View
- Balcony/Terrace
- View
£312/Night
7 Nights - £2,185
Villa
10.0Exceptional
(44 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
£550/Night
7 Nights - £3,848
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Fireplace/Heating
- Pool
- View
- Parking
£2,093/Night
7 Nights - £14,652
Villa
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
£452/Night
7 Nights - £3,164
Villa
10.0Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
£281/Night
7 Nights - £1,969
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
£345/Night
7 Nights - £2,412
Villa
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£555/Night
7 Nights - £3,883
Wheelchair Accessible Holiday Homes in Downtown
Over 424+ Wheelchair Accessible Holiday Homes in or Near Downtown
Condo
10.0Exceptional
(164 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£270/Night
7 Nights - £1,887
Resort
8.5Fabulous
(1206 Reviews)
12 Baths
38 Guests
473.62 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£205/Night
7 Nights - £1,434
Condo
8.2Excellent
(831 Reviews)
1 Bedroom
2 Baths
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
£196/Night
7 Nights - £1,370
Condo
10.0Exceptional
(159 Reviews)
3 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
£431/Night
7 Nights - £3,020
House
8.2Excellent
(166 Reviews)
13 Bedrooms
10 Baths
28 Guests
171.32 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£426/Night
7 Nights - £2,984
Condo
10.0Exceptional
(143 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£370/Night
7 Nights - £2,588
Condo
10.0Exceptional
(125 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
£475/Night
7 Nights - £3,326
Condo
10.0Exceptional
(103 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
£521/Night
7 Nights - £3,649
Condo
10.0Exceptional
(72 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
£280/Night
7 Nights - £1,960
Downtown Private Villas and Holiday Homes Under $200
Over 72+ Downtown Private Villas and Holiday Homes Under $200
Condo
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Spa
- Pool
- Ocean View
£135/Night
7 Nights - £945
Boat Rental
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
5 Guests
- Pool
- Pet Friendly
- Parking
- Air Conditioner
£144/Night
7 Nights - £1,011
Condo
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Spa
- Pool
£143/Night
7 Nights - £1,001
Resort
8.0Excellent
(600 Reviews)
3 Baths
38 Guests
315.74 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£146/Night
7 Nights - £1,019
Condo
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
1350 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
£133/Night
7 Nights - £933
House
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
985 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£125/Night
7 Nights - £873
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1350 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
£134/Night
7 Nights - £941
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
810 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£133/Night
7 Nights - £929
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
806 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£130/Night
7 Nights - £907
Instantly Bookable Holiday Homes in Downtown
Over 890+ Instantly Bookable Holiday Homes in or Near Downtown
House
10.0Exceptional
(78 Reviews)
2 Bedrooms
1 Bath
4 Guests
1080 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£808/Night
7 Nights - £5,653
Condo
9.4Exceptional
(113 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
£297/Night
7 Nights - £2,083
Condo
10.0Exceptional
(54 Reviews)
2 Bedrooms
1 Bath
6 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
£675/Night
7 Nights - £4,726
Condo
10.0Exceptional
(52 Reviews)
2 Bedrooms
1 Bath
4 Guests
646 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£393/Night
7 Nights - £2,751
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
£406/Night
7 Nights - £2,840
Boat Rental
10.0Exceptional
(26 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£473/Night
7 Nights - £3,309
Condo
10.0Exceptional
(25 Reviews)
3 Bedrooms
2 Baths
6 Guests
798 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£284/Night
7 Nights - £1,990
Condo
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
£360/Night
7 Nights - £2,523
Apartment
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
6 Guests
1250 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£561/Night
7 Nights - £3,929
Book a Last Minute Place to Stay in Downtown
About Casai's Private Villas and Holiday Rentals in Downtown
Discover more than 1516 vacation rentals available in Downtown. 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 Downtown.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Downtown, 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 Downtown. On average, places to stay near Downtown offer 815.59 ft², with nightly prices averaging £572.
With Casai, finding and comparing holiday rentals in Downtown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Downtown
| Type | Count |
|---|---|
| Vacation Homes | 543 |
| Holiday Apartments | 169 |
| Villas | 29 |
| Cottages | 13 |
Use these Quick Filters to Find a Holiday Rental in Downtown
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Downtown.
Weather in Downtown, FL
View the weather forecast for Downtown before booking your Downtown Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Other Places to Stay in Downtown, FL
Frequently Asked Questions About Downtown?
What are the top holiday rentals in Downtown?
With numerous options available in Downtown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Downtown:
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Casa Caribe Beautiful tropical 2 bedroom sleeps 6
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Key West Beachfront Luxury 2/2 Condo A212
- Your Condo by the Beach with Ocean View
How many holiday rentals have private pools in Downtown?
Discover a selection of holiday rentals with private pools near Downtown 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.
- Duval Street Suites full kitchen Old Town with heated pool
- Parking, Heated Pool, Pet Friendly - Seagate House
- Luxury 2BR Condo Oceans Edge Resort, Key West
- Duval Street Suites full kitchen, free parking, & heated pool
Which holiday homes in Downtown are best for families?
If you're searching for a family-friendly holiday home in Downtown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Downtown:
- Key West Resort Stay – 2BR Villa Near Beaches & Sunset Views
- NEW Private Pool & Docking - Floralee House
- Duval Dream Loft by Brightwild Right on Duval
How many Casai.uk holiday rentals are available in Downtown?
As of 2026, Casai boasts over 1516 properties listed in the Downtown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Downtown.
Nearby Neighborhood (6)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2147 |
| Old Town Vacation Rentals in Key West, Florida | 2111 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 709 |
| Historic Seaport Vacation Rentals in Key West, Florida | 313 |
| Truman Annex Vacation Rentals in Key West, Florida | 277 |
| Bahama Village Vacation Rentals in Key West, Florida | 70 |
People Also Ask
Finding the best prices in Downtown
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