Condo
10.0(219 Reviews)
2 Bedrooms
4 Guests
Oceanfront
Parking
Pool
Ocean View
CA $613/Night
7 Nights - CA $4,291
Old Town Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Old Town
10.0
CA $1,358/Night
7 Nights - CA $9,507
House
10.0(5 Reviews)
1 Bedroom
Child Friendly
CA $600/Night
7 Nights - CA $4,199
Condo
10.0(194 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $434/Night
7 Nights - CA $3,040
House
10.0(4 Reviews)
1 Bedroom
3 Guests
View
Pet Friendly- Child Friendly
Security/Safety
CA $519/Night
7 Nights - CA $3,630
House
10.0(193 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $1,063/Night
7 Nights - CA $7,438
House
10.0(189 Reviews)
2 Bedrooms
6 Guests
Private Pool- Pool
Balcony/Terrace
Kitchen
CA $1,243/Night
7 Nights - CA $8,699
Condo
10.0(178 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $281/Night
7 Nights - CA $1,966
Condo
10.0(173 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
Hot Tub- Parking
- Pool
CA $836/Night
7 Nights - CA $5,856
Luxury Holiday Rentals in Old Town
Over 3551+ Luxury Holiday Rentals in or Near Old Town
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Boat Rental
4 Bedrooms
6 Guests
- Parking
- Kitchen
Air Conditioner
Internet
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New
House
2 Bedrooms
4 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
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New
Boat Rental
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
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Boat Rental
6 Bedrooms
12 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $10,831/Night
7 Nights - CA $75,814
Top-Rated Holiday Rentals with a Pool in Old Town
Over 2559+ The Best Private Villas and Holiday Rentals in Old Town with a Pool
House
10.0(251 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $820/Night
7 Nights - CA $5,740
House
10.0(218 Reviews)
3 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $820/Night
7 Nights - CA $5,740
Cottage
10.0(209 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $326/Night
7 Nights - CA $2,282
House
10.0(199 Reviews)
3 Bedrooms
7 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $1,481/Night
7 Nights - CA $10,370
House
10.0(182 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Kitchen
CA $1,466/Night
7 Nights - CA $10,259
Condo
10.0(169 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $448/Night
7 Nights - CA $3,133
Condo
10.0(164 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $663/Night
7 Nights - CA $4,639
Condo
10.0(154 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $779/Night
7 Nights - CA $5,455
House
10.0(153 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
Breakfast- Parking
CA $2,234/Night
7 Nights - CA $15,638
Pet-Friendly Holiday Rentals in Old Town
Over 1032+ Pet-Friendly Holiday Rentals in or Near Old Town
Apartment
10.0(99 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
CA $474/Night
7 Nights - CA $3,315
CA $1,908/Night
7 Nights - CA $13,354
Apartment
10.0(1 Review)
1 Bedroom
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $1,122/Night
7 Nights - CA $7,852
Condo
10.0(76 Reviews)
1 Bedroom
4 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $614/Night
7 Nights - CA $4,300
House
10.0(2 Reviews)
6 Bedrooms
16 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $2,701/Night
7 Nights - CA $18,904
Condo
10.0(69 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $1,059/Night
7 Nights - CA $7,416
House
10.0(42 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
CA $958/Night
7 Nights - CA $6,706
House
10.0(40 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
CA $1,882/Night
7 Nights - CA $13,173
Condo
10.0(35 Reviews)
2 Bedrooms
6 Guests
- Pool
- Kitchen
- Internet
- Pet Friendly
CA $687/Night
7 Nights - CA $4,808
Large Holiday Rentals and Private Villas in Old Town
Over 309+ Large Holiday Rentals and Private Villas in or Near Old Town
Villa
10.0(64 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $1,083/Night
7 Nights - CA $7,578
House
10.0(2 Reviews)
6 Bedrooms
14 Guests
- Parking
- Pool
- View
- Air Conditioner
CA $2,014/Night
7 Nights - CA $14,096
Villa
7.4(3 Reviews)
1 Bedroom
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $600/Night
7 Nights - CA $4,199
Villa
10.0(25 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $445/Night
7 Nights - CA $3,113
House
10.0(1 Review)
4 Bedrooms
12 Guests
- Parking
- Pool
- Balcony/Terrace
- View
CA $4,022/Night
7 Nights - CA $28,155
Villa
10.0(22 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
CA $716/Night
7 Nights - CA $5,015
Villa
10.0(10 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
CA $721/Night
7 Nights - CA $5,045
Villa
10.0(3 Reviews)
1 Bedroom
2 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
CA $523/Night
7 Nights - CA $3,661
House
10.0(2 Reviews)
2 Bedrooms
14 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $2,293/Night
7 Nights - CA $16,054
Wheelchair Accessible Holiday Homes in Old Town
Over 647+ Wheelchair Accessible Holiday Homes in or Near Old Town
Condo
10.0(152 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $836/Night
7 Nights - CA $5,854
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Pool
- Balcony/Terrace
- View
- Air Conditioner
CA $675/Night
7 Nights - CA $4,727
CA $471/Night
7 Nights - CA $3,295
Condo
10.0(129 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $813/Night
7 Nights - CA $5,687
Apartment
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- View
- Air Conditioner
CA $393/Night
7 Nights - CA $2,753
Condo
10.0(74 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $492/Night
7 Nights - CA $3,445
CA $1,001/Night
7 Nights - CA $7,007
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
Spa
CA $902/Night
7 Nights - CA $6,311
Condo
10.0(33 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $809/Night
7 Nights - CA $5,662
Old Town Private Villas and Holiday Homes Under $200
Over 224+ Old Town Private Villas and Holiday Homes Under $200
Apartment
10.0(28 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $201/Night
7 Nights - CA $1,406
CA $271/Night
7 Nights - CA $1,895
Bed & Breakfast
9.8(191 Reviews)
1 Bedroom
- Breakfast
- Parking
- Pool
- Balcony/Terrace
CA $265/Night
7 Nights - CA $1,858
House
10.0(12 Reviews)
1 Bedroom
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $232/Night
7 Nights - CA $1,624
Boat Rental
6.3(12 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Air Conditioner
CA $232/Night
7 Nights - CA $1,621
House
10.0(11 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $273/Night
7 Nights - CA $1,908
House
10.0(11 Reviews)
1 Bedroom
4 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
CA $248/Night
7 Nights - CA $1,737
House
10.0(10 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
CA $279/Night
7 Nights - CA $1,949
CA $248/Night
7 Nights - CA $1,740
Instantly Bookable Holiday Homes in Old Town
Over 2249+ Instantly Bookable Holiday Homes in or Near Old Town
Cottage
10.0(169 Reviews)
2 Bedrooms
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $614/Night
7 Nights - CA $4,298
House
10.0(6 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $372/Night
7 Nights - CA $2,602
House
10.0(135 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $1,121/Night
7 Nights - CA $7,847
Condo
10.0(126 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $367/Night
7 Nights - CA $2,566
House
10.0(111 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $485/Night
7 Nights - CA $3,396
Condo
10.0(108 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $540/Night
7 Nights - CA $3,780
House
10.0(107 Reviews)
1 Bedroom
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $466/Night
7 Nights - CA $3,264
House
10.0(104 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $664/Night
7 Nights - CA $4,650
Apartment
10.0(92 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $987/Night
7 Nights - CA $6,910
Book a Last Minute Place to Stay in Old Town
About Casai's Private Villas and Holiday Rentals in Old Town
Discover more than 3560 vacation rentals available in Old Town. 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 Old Town.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Town, 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 Old Town. On average, places to stay near Old Town offer 739.26 ft², with nightly prices averaging CA $1,046.
With Casai, finding and comparing holiday rentals in Old Town 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 Old Town, FL
There are 3560 Old Town, FL Holiday Rentals
- Prices for a holiday home in Old Town start at CA $158
- Top rated vacation home in Old Town is Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Most popular short term in Old Town is Blue Marlin Motel
- Cheapest place to stay in Old Town is Conch Republic Studio - Key West Millionaires Row
- Most expensive holiday rental in Old Town is Beachfront Key West + Free Breakfast, Bar & Pool
Recently Booked Holiday Rentals in Old Town
Frequently Asked Questions About Old Town?
What are the top holiday rentals in Old Town?
With numerous options available in Old Town, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Town:
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Walkable Cottage w/Pool Access in Key West!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- Everything Key West has to offer @ Mango Cottage
- ~ VILLA JOSINE ~ 4 B/4.5 BA large designer home with pool in a great location
- Central Condo w/Deck & Pool Access in Key West!
How many holiday rentals have private pools in Old Town?
Discover a selection of holiday rentals with private pools near Old Town 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 Old Town are best for families?
If you're searching for a family-friendly holiday home in Old Town, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Town:
How many Casai.ca holiday rentals are available in Old Town?
As of 2026, Casai boasts over 3560 properties listed in the Old Town area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Town.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2107 |
| Downtown Vacation Rentals in Key West, Florida | 850 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 714 |
| Historic Seaport Vacation Rentals in Key West, Florida | 319 |
| Truman Annex Vacation Rentals in Key West, Florida | 237 |
| Meadows Vacation Rentals in Key West, Florida | 104 |
| The Meadows Vacation Rentals in Key West, Florida | 104 |
| Bahama Village Vacation Rentals in Key West, Florida | 62 |
| Midtown Vacation Rentals in Key West, Florida | 40 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4477 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4473 |
