Estia Villas - Vacation Rentals in Old Town
House
9.5
(
19 Reviews
)
2 Bedrooms
5 Bathrooms
8 Guests
742.71 ft²
-
Pool -
Ocean View -
View -
Air Conditioner
US $258
/Night
7 Nights - $1,806
Villa
10.0
(
63 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
850 ft²
-
Hot Tub -
Parking -
Pool
-
Balcony/Terrace
US $760
/Night
7 Nights - $5,319
Villa
7.4
(
3 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
US $421
/Night
7 Nights - $2,947
Villa
10.0
(
25 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
350 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $417
/Night
7 Nights - $2,920
Villa
10.0
(
21 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
550 ft²
-
Hot Tub
-
Breakfast -
Parking
-
Pool
US $503
/Night
7 Nights - $3,520
Villa
10.0
(
10 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
500 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $353
/Night
7 Nights - $2,470
Villa
10.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
200 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $367
/Night
7 Nights - $2,570
Villa
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
4 Guests
350 ft²
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
US $417
/Night
7 Nights - $2,920
See More Old Town Vacation Rentals
Luxury Places to Stay in Old Town
Over 3616+
Luxury Places to Stay in or Near Old Town
House
4 Bedrooms
4 Bathrooms
8 Guests
3175.35 ft²
-
Parking
-
Pool
-
Spa -
Internet
Unlock the Best Price
Boat Rental
6 Bedrooms
6 Bathrooms
12 Guests
2400 ft²
-
Ocean View
-
Balcony/Terrace
-
View
-
Kitchen
US $7,602
/Night
7 Nights - $53,214
House
9.5
(
2 Reviews
)
6 Bedrooms
6 Bathrooms
24 Guests
2400.35 ft²
-
EV Charge Station -
Parking
-
Pool
-
Balcony/Terrace
US $6,002
/Night
7 Nights - $42,014
House
8 Bedrooms
10 Bathrooms
20 Guests
3702.79 ft²
-
Parking
-
Pool
-
Spa
-
Internet
US $5,694
/Night
7 Nights - $39,858
House
4 Bedrooms
4 Bathrooms
8 Guests
1679.17 ft²
-
Parking
-
Pool
-
Spa
-
Internet
US $5,347
/Night
7 Nights - $37,429
New
House
10 Bedrooms
7 Bathrooms
30 Guests
5133 ft²
-
Oceanfront -
Parking
-
Pool
-
Ocean View
US $5,344
/Night
7 Nights - $37,405
House
6 Bedrooms
7 Bathrooms
12 Guests
4004.17 ft²
-
Parking
-
Pool
-
View
-
Air Conditioner
US $5,186
/Night
7 Nights - $36,302
House
10.0
(
14 Reviews
)
11 Bedrooms
5 Bathrooms
20 Guests
5000 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $5,146
/Night
7 Nights - $36,019
See More Old Town Luxury Vacation Rentals
Find More Old Town Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Old Town
Over 2632+
Top-Rated Vacation Rentals with a Pool in or Near Old Town
US $262
/Night
7 Nights - $1,836
House
10.0
(
250 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $727
/Night
7 Nights - $5,088
Condo
10.0
(
219 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
700 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $333
/Night
7 Nights - $2,329
House
10.0
(
218 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1500 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $790
/Night
7 Nights - $5,527
Cottage
10.0
(
209 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $229
/Night
7 Nights - $1,602
House
10.0
(
204 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1154 ft²
-
Private Pool -
Oceanfront
-
Parking
-
Pool
US $1,307
/Night
7 Nights - $9,148
House
10.0
(
199 Reviews
)
3 Bedrooms
3 Bathrooms
7 Guests
1855 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $1,102
/Night
7 Nights - $7,716
House
10.0
(
193 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1080 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $659
/Night
7 Nights - $4,611
Pet-Friendly Vacation Rentals in Old Town
Over 1041+
Pet-Friendly Vacation Rentals in or Near Old Town
House
2 Bedrooms
2 Bathrooms
4 Guests
968.75 ft²
-
Hot Tub
-
Air Conditioner
-
Internet
-
Pet Friendly
US $238
/Night
7 Nights - $1,666
House
9.6
(
235 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $738
/Night
7 Nights - $5,167
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Parking
-
Balcony/Terrace
-
Internet
-
Pet Friendly
US $1,713
/Night
7 Nights - $11,993
Condo
9.8
(
93 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1900 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $703
/Night
7 Nights - $4,924
House
10.0
(
28 Reviews
)
5 Bedrooms
4 Bathrooms
8 Guests
3173 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,872
/Night
7 Nights - $13,106
House
10.0
(
144 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
2651 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $1,474
/Night
7 Nights - $10,321
House
10.0
(
36 Reviews
)
5 Bedrooms
4 Bathrooms
13 Guests
2116 ft²
-
Oceanfront
-
Parking
-
Ocean View
-
Balcony/Terrace
US $1,122
/Night
7 Nights - $7,856
House
9.8
(
137 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1541 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $795
/Night
7 Nights - $5,565
See More Pet-Friendly Vacation Rentals in Old Town on PetFriendly.io
Large Vacation Homes & Villas in Old Town
Over 302+
Large Vacation Homes & Villas in or Near Old Town
House
10.0
(
2 Reviews
)
6 Bedrooms
7 Bathrooms
14 Guests
2895.49 ft²
-
Parking
-
Pool
-
View
-
Air Conditioner
US $2,969
/Night
7 Nights - $20,783
House
10.0
(
152 Reviews
)
5 Bedrooms
4 Bathrooms
12 Guests
2700 ft²
-
Private Pool
-
Oceanfront
-
Breakfast
-
Parking
US $1,632
/Night
7 Nights - $11,422
House
10.0
(
83 Reviews
)
5 Bedrooms
6 Bathrooms
8 Guests
3920 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,501
/Night
7 Nights - $10,506
House
8.8
(
48 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1690 ft²
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
US $1,170
/Night
7 Nights - $8,188
House
9.4
(
29 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
1 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Child Friendly
US $552
/Night
7 Nights - $3,863
House
9.8
(
87 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
2000 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $1,061
/Night
7 Nights - $7,425
House
9.6
(
92 Reviews
)
10 Bedrooms
5 Bathrooms
22 Guests
9600 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,883
/Night
7 Nights - $13,181
House
9.4
(
26 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1600 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $260
/Night
7 Nights - $1,818
See More Family Vacation Rentals in Old Town on FVR
Wheelchair Accessible Vacation Homes in Old Town
Over 670+
Wheelchair Accessible Vacation Homes in or Near Old Town
House
7.3
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
2185.07 ft²
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $225
/Night
7 Nights - $1,575
Condo
9.6
(
168 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $249
/Night
7 Nights - $1,742
Bed & Breakfast
9.4
(
1006 Reviews
)
1 Bedroom
1 Bathroom
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
US $224
/Night
7 Nights - $1,567
Condo
10.0
(
164 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1357 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $494
/Night
7 Nights - $3,455
Condo
10.0
(
128 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1357 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $599
/Night
7 Nights - $4,194
Condo
9.8
(
186 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1357 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $487
/Night
7 Nights - $3,408
Condo
9.8
(
170 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1357 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $493
/Night
7 Nights - $3,452
Condo
9.8
(
128 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1357 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $654
/Night
7 Nights - $4,577
Old Town Vacation Rentals and Airbnb Places to Stay Under $200
Over 266+
Old Town Vacation Rentals and Airbnb Places to Stay Under $200
House
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
2 Guests
710.42 ft²
-
Parking
-
Pool
-
View
-
Air Conditioner
US $190
/Night
7 Nights - $1,330
Condo
9.4
(
81 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $149
/Night
7 Nights - $1,041
Bed & Breakfast
9.6
(
1096 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $136
/Night
7 Nights - $950
Condo
9.8
(
35 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
800 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $173
/Night
7 Nights - $1,209
House
9.6
(
10 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1461 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $196
/Night
7 Nights - $1,375
Cottage
9.8
(
16 Reviews
)
1 Bedroom
1 Bathroom
4 Guests
544 ft²
-
Oceanfront
-
Pool
-
Ocean View
-
Balcony/Terrace
US $170
/Night
7 Nights - $1,188
Condo
9.2
(
69 Reviews
)
1 Bedroom
1 Bathroom
2 Guests
1 ft²
-
Private Pool
-
Oceanfront
-
Parking
-
Pool
US $172
/Night
7 Nights - $1,204
House
9.6
(
82 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
600 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $192
/Night
7 Nights - $1,342
See More Old Town Vacation Rental Deals
Instantly Bookable Vacation Homes in Old Town
Over 2264+
Instantly Bookable Vacation Homes in or Near Old Town
Condo
9.8
(
103 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
700 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $279
/Night
7 Nights - $1,954
Apartment
1 Bedroom
2 Bathrooms
2 Guests
-
Air Conditioner
-
Internet
-
Laundry -
Bedding/Linens
US $513
/Night
7 Nights - $3,594
House
9.6
(
108 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1420 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $519
/Night
7 Nights - $3,634
Condo
9.0
(
51 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
680 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $209
/Night
7 Nights - $1,462
Condo
10.0
(
63 Reviews
)
2 Bedrooms
1 Bathroom
4 Guests
680 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $250
/Night
7 Nights - $1,753
Condo
10.0
(
52 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1770 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $322
/Night
7 Nights - $2,256
Condo
9.8
(
193 Reviews
)
2 Bedrooms
1 Bathroom
6 Guests
795 ft²
-
Oceanfront
-
Ocean View
-
Balcony/Terrace
-
View
US $465
/Night
7 Nights - $3,256
House
9.8
(
148 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1420 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $558
/Night
7 Nights - $3,908
See More Old Town Short-Term Vacation Rentals
About Old Town Vacation Rentals
With more than 41 Old Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Old Town.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Old Town, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Old Town. Places to stay near Old Town are 935.69 ft² on average, with prices averaging US $682 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Old Town with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Use these Quick Filters to Find a Vacation Rental in Old Town
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Old Town.
Weather in Old Town
View the weather forecast for Old Town before booking your Old Town 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
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Complexes around Old Town, FL
Key West
84 Properties
Southernmost West
14 Properties
Curry
9 Properties
Duval Street
5 Properties
Hyatt Windward Pointe
4 Properties
Atlantic Paradise
3 Properties
Courtyard
3 Properties
Kimpton Lighthouse Hotel Ihg
3 Properties
Linger
3 Properties
Livin
3 Properties
Parrot Hotel Villas
3 Properties
Artist Garden
2 Properties
Bamboo The Annex
2 Properties
Duval West
2 Properties
Town Introductory Rates
1 Properties
Old Town Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Old Town?
There are a lot of options in Old Town. If you plan on staying in the Old Town area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Old Town:
- Two Bedroom Two Bath Poolside Villa Steps from Duval!
- Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
- Poolside Studio Villa Steps from Duval!
- Loft Villa Steps from Duval!
- One Bedroom Deck Villa Steps from Duval!
- VILLA BELLA - AN EXCEPTIONAL 5/4 ISLAND HOME-Convenient to Old Town
- Poolside Queen Room Steps from Duval!
- Poolside King Room Steps from Duval!
- Location In Down Town Key West W/2 Pools, Huge Private Roof Deck & Parking
- Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool
How many vacation rentals have private pools in Old Town?
There are 587 vacation rentals with private pools near Old Town. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Old Town are best for families?
If you are looking for a family-friendly vacation home in Old Town, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Old Town:
How many vacation rentals are available in Old Town?
Currently, the total number of properties listed in 2026 is over 41 in the Old Town area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Old Town.
