4556+ Private Villas and Holiday Rentals in White St. Gallery |
White St. Gallery Holiday Rentals
New
House
4 Bedrooms
4 Baths
8 Guests
2386 ft²
Private Pool
Hot Tub
Fireplace/Heating
Pool
CA $1,988/Night
7 Nights - CA $13,916
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
2002.09 ft²
- Pool
View
Breakfast
Parking
CA $1,325/Night
7 Nights - CA $9,277
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.15 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
Ocean View
Balcony/Terrace- View
Pet Friendly
CA $783/Night
7 Nights - CA $5,480
New
House
3 Bedrooms
3 Baths
6 Guests
1615 ft²
- Private Pool
Oceanfront- Pool
- Ocean View
CA $1,443/Night
7 Nights - CA $10,102
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Pet Friendly
Child Friendly
Security/Safety
CA $506/Night
7 Nights - CA $3,542
House
- Key West
- ·
- Key West Historic District
- 0.10 mi to center
4 Bedrooms
3 Baths
8 Guests
1600 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,050/Night
7 Nights - CA $7,353
New
House
2 Bedrooms
2 Baths
4 Guests
1099 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $459/Night
7 Nights - CA $3,214
House
3 Bedrooms
3 Baths
5 Guests
- Pet Friendly
Air Conditioner
Internet- Child Friendly
CA $295/Night
7 Nights - CA $2,064
New
Condo
2 Bedrooms
2 Baths
4 Guests
772 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $264/Night
7 Nights - CA $1,850
Luxury Holiday Rentals in White St. Gallery
Over 4547+ Luxury Holiday Rentals in or Near White St. Gallery
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
New
Hotel
- Key West
- ·
- Uptown - Upper Duval
- 0.07 mi to center
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
Unlock the Best Price
Top-Rated Holiday Rentals with a Pool in White St. Gallery
Over 3356+ The Best Private Villas and Holiday Rentals in White St. Gallery with a Pool
Hotel
10.0Exceptional
(1003 Reviews)
1 Bath
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
CA $432/Night
7 Nights - CA $3,025
Cottage
10.0Exceptional
(238 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,066/Night
7 Nights - CA $7,458
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.16 mi to center
10.0Exceptional
(233 Reviews)
4 Bedrooms
2 Baths
7 Guests
1440 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
CA $1,281/Night
7 Nights - CA $8,967
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(232 Reviews)
2 Bedrooms
1 Bath
4 Guests
674 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $330/Night
7 Nights - CA $2,309
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(218 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $493/Night
7 Nights - CA $3,453
House
10.0Exceptional
(208 Reviews)
3 Bedrooms
3 Baths
8 Guests
1875 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $2,714/Night
7 Nights - CA $18,997
House
- Key West
- ·
- Uptown - Upper Duval
- 0.02 mi to center
10.0Exceptional
(202 Reviews)
3 Bedrooms
3 Baths
6 Guests
1154 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $1,500/Night
7 Nights - CA $10,499
House
10.0Exceptional
(194 Reviews)
3 Bedrooms
3 Baths
7 Guests
1855 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
CA $1,879/Night
7 Nights - CA $13,152
House
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
2 Baths
4 Guests
1080 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $815/Night
7 Nights - CA $5,708
Pet-Friendly Holiday Rentals in White St. Gallery
Over 1330+ Pet-Friendly Holiday Rentals in or Near White St. Gallery
Apartment
10.0Exceptional
(96 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
CA $497/Night
7 Nights - CA $3,478
House
- Key West
- ·
- Uptown - Upper Duval
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
CA $1,154/Night
7 Nights - CA $8,076
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Pet Friendly
- Parking
CA $1,313/Night
7 Nights - CA $9,189
Condo
10.0Exceptional
(72 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $608/Night
7 Nights - CA $4,257
House
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
8 Guests
882.64 ft²
- View
- Breakfast
- Pet Friendly
- Child Friendly
CA $744/Night
7 Nights - CA $5,206
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(61 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $680/Night
7 Nights - CA $4,763
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(38 Reviews)
3 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $1,237/Night
7 Nights - CA $8,657
House
- Key West
- ·
- Uptown - Upper Duval
- 0.09 mi to center
10.0Exceptional
(34 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
CA $1,705/Night
7 Nights - CA $11,935
Condo
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $889/Night
7 Nights - CA $6,225
Large Holiday Rentals and Private Villas in White St. Gallery
Over 457+ Large Holiday Rentals and Private Villas in or Near White St. Gallery
Villa
10.0Exceptional
(57 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
CA $1,085/Night
7 Nights - CA $7,597
House
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
4 Baths
12 Guests
2346.53 ft²
- Internet
- Child Friendly
Laundry- Security/Safety
CA $3,744/Night
7 Nights - CA $26,210
Villa
10.0Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
CA $854/Night
7 Nights - CA $5,976
House
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
12 Guests
2443.41 ft²
- Fireplace/Heating
- Pool
- View
- Parking
CA $3,925/Night
7 Nights - CA $27,473
Villa
10.0Exceptional
(24 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
CA $452/Night
7 Nights - CA $3,164
Villa
10.0Exceptional
(19 Reviews)
2 Bedrooms
1 Bath
4 Guests
550 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
CA $527/Night
7 Nights - CA $3,692
Villa
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
CA $646/Night
7 Nights - CA $4,522
Villa
10.0Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $1,040/Night
7 Nights - CA $7,280
Villa
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
200 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Breakfast
CA $401/Night
7 Nights - CA $2,808
Wheelchair Accessible Holiday Homes in White St. Gallery
Over 1100+ Wheelchair Accessible Holiday Homes in or Near White St. Gallery
Condo
10.0Exceptional
(168 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
CA $774/Night
7 Nights - CA $5,419
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Ocean View
- View
- Pet Friendly
- Parking
CA $384/Night
7 Nights - CA $2,686
Bed & Breakfast
- Key West
- ·
- Bahama Village
- 0.09 mi to center
9.4Exceptional
(1003 Reviews)
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Breakfast
- Parking
CA $274/Night
7 Nights - CA $1,920
Condo
10.0Exceptional
(166 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
CA $427/Night
7 Nights - CA $2,987
Resort
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
9.5Exceptional
(508 Reviews)
3 Baths
6 Guests
419.79 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $2,347/Night
7 Nights - CA $16,426
Condo
10.0Exceptional
(161 Reviews)
3 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
CA $705/Night
7 Nights - CA $4,932
Condo
10.0Exceptional
(145 Reviews)
2 Bedrooms
2 Baths
6 Guests
1463 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
CA $683/Night
7 Nights - CA $4,784
Condo
10.0Exceptional
(127 Reviews)
2 Bedrooms
2 Baths
6 Guests
1357 ft²
- Oceanfront
- Hot Tub
- Spa
- Pool
CA $810/Night
7 Nights - CA $5,673
Condo
10.0Exceptional
(72 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
CA $525/Night
7 Nights - CA $3,674
White St. Gallery Private Villas and Holiday Homes Under $200
Over 296+ White St. Gallery Private Villas and Holiday Homes Under $200
House
- Key West
- ·
- Truman Annex
- 0.19 mi to center
1 Bedroom
1 Bath
2 Guests
5522 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
CA $250/Night
7 Nights - CA $1,752
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
710.42 ft²
- Pool
- View
- Pet Friendly
- Parking
CA $264/Night
7 Nights - CA $1,849
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.16 mi to center
9.8Exceptional
(438 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
CA $228/Night
7 Nights - CA $1,597
House
- Key West
- ·
- Bahama Village
- 0.11 mi to center
10.0Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $266/Night
7 Nights - CA $1,861
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
9.0Exceptional
(1414 Reviews)
11 Bedrooms
7 Baths
18 Guests
235.27 ft²
- Balcony/Terrace
- View
- Air Conditioner
- Internet
CA $277/Night
7 Nights - CA $1,937
Condo
10.0Exceptional
(31 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
CA $196/Night
7 Nights - CA $1,368
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $258/Night
7 Nights - CA $1,806
Apartment
10.0Exceptional
(27 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $193/Night
7 Nights - CA $1,351
Condo
- Key West
- ·
- Truman Annex
- 0.17 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
513 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
CA $267/Night
7 Nights - CA $1,867
Instantly Bookable Holiday Homes in White St. Gallery
Over 2957+ Instantly Bookable Holiday Homes in or Near White St. Gallery
Hotel
3 Baths
- Pool
- Kitchen
- Parking
- Air Conditioner
CA $1,270/Night
7 Nights - CA $8,887
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1266 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $363/Night
7 Nights - CA $2,538
Condo
- Key West
- ·
- Truman Annex
- 0.20 mi to center
10.0Exceptional
(192 Reviews)
2 Bedrooms
1 Bath
5 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $381/Night
7 Nights - CA $2,666
House
- Key West
- ·
- Bahama Village
- 0.11 mi to center
10.0Exceptional
(162 Reviews)
2 Bedrooms
2 Baths
4 Guests
950 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $610/Night
7 Nights - CA $4,268
Cottage
- Key West
- ·
- Bahama Village
- 0.13 mi to center
10.0Exceptional
(159 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
CA $505/Night
7 Nights - CA $3,535
House
10.0Exceptional
(137 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,085/Night
7 Nights - CA $7,597
House
- Key West
- ·
- Key West Historic District
- 0.12 mi to center
10.0Exceptional
(129 Reviews)
2 Bedrooms
2 Baths
4 Guests
840 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
CA $877/Night
7 Nights - CA $6,139
Condo
- Key West
- ·
- Truman Annex
- 0.19 mi to center
10.0Exceptional
(125 Reviews)
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
CA $398/Night
7 Nights - CA $2,786
House
- Key West
- ·
- The Meadows
- 0.07 mi to center
10.0Exceptional
(123 Reviews)
2 Bedrooms
2 Baths
6 Guests
1224 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
CA $1,912/Night
7 Nights - CA $13,386
Book a Last Minute Place to Stay in White St. Gallery
About Casai's Private Villas and Holiday Rentals in White St. Gallery
Discover more than 4556 vacation rentals available in White St. Gallery. 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 White St. Gallery.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in White St. Gallery, 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 White St. Gallery. On average, places to stay near White St. Gallery offer 733.75 ft², with nightly prices averaging CA $1,064.
With Casai, finding and comparing holiday rentals in White St. Gallery 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 White St. Gallery
| Type | Count |
|---|---|
| Vacation Homes | 2192 |
| Holiday Apartments | 608 |
| Cottages | 114 |
| Villas | 38 |
Use these Quick Filters to Find a Holiday Rental in White St. Gallery
★ 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 White St. Gallery.
Weather in White St. Gallery, FL
View the weather forecast for White St. Gallery before booking your White St. Gallery 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
Frequently Asked Questions About White St. Gallery?
What are the top holiday rentals in White St. Gallery?
With numerous options available in White St. Gallery, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in White St. Gallery:
- Almond Tree Inn Hotel - Adults Only
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Perfect Location, nPrivate Heated Pool,nPristine Luxury Home!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
How many holiday rentals have private pools in White St. Gallery?
Discover a selection of holiday rentals with private pools near White St. Gallery 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.
- Everything Key West has to offer @ Mango Cottage
- Key West Harbor Inn - Adults Only
- Tropical Oasis in the Truman Annex with a private pool
- Perfect Pineapple by AvantStay Pet Friendly w Pool Month Long Stays Only
Which holiday homes in White St. Gallery are best for families?
If you're searching for a family-friendly holiday home in White St. Gallery, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in White St. Gallery:
- Everything Key West has to offer @ Mango Cottage
- Somewhere on the beach
- Atlantic Paradise by Avantstay Great Location w/Balcony, Outdoor Dining & Shared Pool & Hot Tub!
How many Casai.ca holiday rentals are available in White St. Gallery?
As of 2026, Casai boasts over 4556 properties listed in the White St. Gallery area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in White St. Gallery.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2292 |
| Old Town Vacation Rentals in Key West, Florida | 2210 |
| The Meadows Vacation Rentals in Key West, Florida | 103 |
| Midtown Vacation Rentals in Key West, Florida | 43 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4527 |
People Also Ask
Finding the best prices in White St. Gallery
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