Condo
10.0(314 Reviews)
2 Bedrooms
6 Guests
Oceanfront
Hot Tub
Parking
Pool
CA $522/Night
7 Nights - CA $3,658
Pensacola Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Pensacola
10.0
House
10.0(12 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
Ocean View
Balcony/Terrace
CA $442/Night
7 Nights - CA $3,095
Cottage
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
Kitchen
Air Conditioner
CA $233/Night
7 Nights - CA $1,634
Condo
10.0(309 Reviews)
1 Bedroom
6 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $530/Night
7 Nights - CA $3,713
CA $360/Night
7 Nights - CA $2,523
Condo
10.0(292 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $479/Night
7 Nights - CA $3,350
Condo
10.0(265 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $393/Night
7 Nights - CA $2,754
Condo
10.0(264 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $579/Night
7 Nights - CA $4,054
Condo
10.0(260 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $447/Night
7 Nights - CA $3,132
Luxury Holiday Rentals in Pensacola
Over 9362+ Luxury Holiday Rentals in or Near Pensacola
House
3 Bedrooms
6 Guests
- Parking
- Air Conditioner
Internet
Child Friendly
CA $8,207/Night
7 Nights - CA $57,451
House
10.0(2 Reviews)
5 Bedrooms
10 Guests
Private Pool- Oceanfront
- Parking
- Pool
CA $8,199/Night
7 Nights - CA $57,395
House
10.0(1 Review)
4 Bedrooms
8 Guests
- Parking
- Internet
Pet Friendly- Child Friendly
CA $4,779/Night
7 Nights - CA $33,454
House
10.0(2 Reviews)
3 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $4,590/Night
7 Nights - CA $32,133
House
10.0(2 Reviews)
7 Bedrooms
24 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $4,573/Night
7 Nights - CA $32,011
House
8 Bedrooms
24 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $4,413/Night
7 Nights - CA $30,889
New
House
1 Bedroom
40 Guests
- Pool
- Ocean View
- Balcony/Terrace
View
CA $4,356/Night
7 Nights - CA $30,490
House
8 Bedrooms
26 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $4,167/Night
7 Nights - CA $29,172
House
10.0(1 Review)
5 Bedrooms
12 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
CA $4,097/Night
7 Nights - CA $28,678
Top-Rated Holiday Rentals with a Pool in Pensacola
Over 4569+ The Best Private Villas and Holiday Rentals in Pensacola with a Pool
Condo
10.0(253 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $378/Night
7 Nights - CA $2,647
Condo
10.0(239 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $517/Night
7 Nights - CA $3,619
Condo
10.0(237 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $406/Night
7 Nights - CA $2,843
Condo
10.0(226 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $464/Night
7 Nights - CA $3,246
Condo
10.0(223 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $352/Night
7 Nights - CA $2,461
House
10.0(214 Reviews)
4 Bedrooms
10 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
CA $751/Night
7 Nights - CA $5,261
Condo
10.0(214 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $516/Night
7 Nights - CA $3,609
Condo
10.0(212 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $443/Night
7 Nights - CA $3,100
Condo
10.0(211 Reviews)
2 Bedrooms
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $567/Night
7 Nights - CA $3,968
Pet-Friendly Holiday Rentals in Pensacola
Over 2215+ Pet-Friendly Holiday Rentals in or Near Pensacola
House
10.0(132 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $218/Night
7 Nights - CA $1,528
House
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- View
CA $147/Night
7 Nights - CA $1,027
House
10.0(5 Reviews)
3 Bedrooms
8 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $405/Night
7 Nights - CA $2,836
House
10.0(121 Reviews)
1 Bedroom
3 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
CA $284/Night
7 Nights - CA $1,990
Apartment
10.0(5 Reviews)
2 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $527/Night
7 Nights - CA $3,687
House
10.0(114 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
CA $222/Night
7 Nights - CA $1,556
Cottage
10.0(110 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $301/Night
7 Nights - CA $2,107
Condo
10.0(104 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $763/Night
7 Nights - CA $5,343
Condo
10.0(94 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $337/Night
7 Nights - CA $2,359
Large Holiday Rentals and Private Villas in Pensacola
Over 1882+ Large Holiday Rentals and Private Villas in or Near Pensacola
Condo
10.0(92 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $608/Night
7 Nights - CA $4,259
House
10.0(5 Reviews)
5 Bedrooms
12 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $586/Night
7 Nights - CA $4,104
CA $776/Night
7 Nights - CA $5,435
Villa
10.0(33 Reviews)
1 Bedroom
3 Guests
- Parking
- Balcony/Terrace
- View
- Kitchen
CA $169/Night
7 Nights - CA $1,184
CA $610/Night
7 Nights - CA $4,272
Villa
10.0(21 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $390/Night
7 Nights - CA $2,732
House
10.0(15 Reviews)
1 Bedroom
10 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $718/Night
7 Nights - CA $5,026
House
10.0(6 Reviews)
2 Bedrooms
10 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $737/Night
7 Nights - CA $5,160
Apartment
10.0(6 Reviews)
2 Bedrooms
10 Guests
Breakfast- Parking
- Balcony/Terrace
- Kitchen
CA $665/Night
7 Nights - CA $4,657
Wheelchair Accessible Holiday Homes in Pensacola
Over 2275+ Wheelchair Accessible Holiday Homes in or Near Pensacola
Condo
10.0(198 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $606/Night
7 Nights - CA $4,240
House
10.0(2 Reviews)
4 Bedrooms
8 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $661/Night
7 Nights - CA $4,625
Cottage
10.0(1 Review)
1 Bedroom
- Parking
- Kitchen
- Air Conditioner
- Internet
CA $1,697/Night
7 Nights - CA $11,878
Condo
10.0(195 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $423/Night
7 Nights - CA $2,962
Apartment
10.0(2 Reviews)
3 Bedrooms
8 Guests
Private Beach- Oceanfront
- Breakfast
- Parking
CA $374/Night
7 Nights - CA $2,618
Condo
10.0(186 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $392/Night
7 Nights - CA $2,743
Condo
10.0(177 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $574/Night
7 Nights - CA $4,022
Condo
10.0(177 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
CA $429/Night
7 Nights - CA $3,005
Condo
10.0(175 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $728/Night
7 Nights - CA $5,096
Pensacola Private Villas and Holiday Homes Under $200
Over 1941+ Pensacola Private Villas and Holiday Homes Under $200
House
10.0(181 Reviews)
1 Bedroom
3 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
CA $201/Night
7 Nights - CA $1,406
House
10.0(6 Reviews)
3 Bedrooms
8 Guests
- Parking
- Child Friendly
Security/Safety
CA $187/Night
7 Nights - CA $1,308
Cottage
10.0(2 Reviews)
1 Bedroom
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $278/Night
7 Nights - CA $1,943
Apartment
10.0(146 Reviews)
2 Bedrooms
8 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
CA $200/Night
7 Nights - CA $1,402
Apartment
10.0(6 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $205/Night
7 Nights - CA $1,434
Condo
10.0(87 Reviews)
1 Bedroom
2 Guests
- Parking
- Pool
Skiing- Ocean View
CA $244/Night
7 Nights - CA $1,709
Condo
10.0(78 Reviews)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Ocean View
CA $233/Night
7 Nights - CA $1,634
Apartment
10.0(66 Reviews)
1 Bedroom
4 Guests
- Kitchen
- Air Conditioner
- Child Friendly
TV
CA $191/Night
7 Nights - CA $1,337
Apartment
10.0(64 Reviews)
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Child Friendly
- TV
CA $234/Night
7 Nights - CA $1,637
Instantly Bookable Holiday Homes in Pensacola
Over 6200+ Instantly Bookable Holiday Homes in or Near Pensacola
Boat Rental
10.0(179 Reviews)
1 Bedroom
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $539/Night
7 Nights - CA $3,772
House
9.8(18 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $333/Night
7 Nights - CA $2,329
Condo
10.0(179 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $519/Night
7 Nights - CA $3,634
Boat Rental
10.0(166 Reviews)
2 Bedrooms
4 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
CA $539/Night
7 Nights - CA $3,772
Condo
10.0(165 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $585/Night
7 Nights - CA $4,098
Condo
10.0(165 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
CA $433/Night
7 Nights - CA $3,032
Condo
10.0(162 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $608/Night
7 Nights - CA $4,259
Condo
10.0(157 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
CA $428/Night
7 Nights - CA $2,996
Condo
10.0(151 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
CA $557/Night
7 Nights - CA $3,898
Book a Last Minute Place to Stay in Pensacola
About Casai's Private Villas and Holiday Rentals in Pensacola
Discover more than 9371 vacation rentals available in Pensacola. 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 Pensacola.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Pensacola, 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 Pensacola. On average, places to stay near Pensacola offer 1195.04 ft², with nightly prices averaging CA $557.
With Casai, finding and comparing holiday rentals in Pensacola 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 Pensacola, FL
There are 9371 Pensacola, FL Holiday Rentals
- Prices for a holiday home in Pensacola start at CA $71
- Top rated vacation home in Pensacola is 𝔾𝕦𝕝𝕗𝔽𝕣𝕠𝕟𝕥 Emerald Isle- "My Blue Heaven" 5-Star Reviews/Walk to All
- Most popular short term in Pensacola is Surf & Sand Hotel - Free Hot Breakfast & Rentals
- Cheapest place to stay in Pensacola is 1-bedroom apartment Hundreds in Discounts after 1st Month rental $
- Most expensive holiday rental in Pensacola is Upgraded Midcentury 3 BDR Home Downtown Pensacola
Frequently Asked Questions About Pensacola?
What are the top holiday rentals in Pensacola?
With numerous options available in Pensacola, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Pensacola:
- 𝔾𝕦𝕝𝕗𝔽𝕣𝕠𝕟𝕥 Emerald Isle- "My Blue Heaven" 5-Star Reviews/Walk to All
- BOOK NOW FOR FALL! - FREE DAILY CHAIR SERVICE UNTIL 10/31/26- 309 VRBO REVIEWS!
- 𝔾𝕦𝕝𝕗𝔽𝕣𝕠𝕟𝕥 𝑬𝒎𝒆𝒓𝒂𝒍𝒅 𝑰𝒔𝒍𝒆 9th Floor Stocked & Stellar Reviews!
- Charming 2 Bedroom Condo on the Water with Sunset Views
- Beachview Complex - Steps from the beach, Swimming pool, and Tennis Court
- Beachside Haven: Spacious 6-Bedroom Retreat Just Steps from the Sand
- Direct Gulf-Front 230+ ★ Reviews “Seas the Day” 2BR/2BA – Villas on the Gulf
- Gulf Front Emerald Isle Condo on 11th floor with Beach Chairs
- 🌴Portofino Island RESORT🌴Hear OCEAN WAVES from balcony
- Gulf Front Condo with Luxury Furnishings and Beach Chairs
How many holiday rentals have private pools in Pensacola?
Discover a selection of holiday rentals with private pools near Pensacola 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 Pensacola are best for families?
If you're searching for a family-friendly holiday home in Pensacola, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Pensacola:
How many Casai.ca holiday rentals are available in Pensacola?
As of 2026, Casai boasts over 9371 properties listed in the Pensacola area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Pensacola.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| Navarre Beach Vacation Rentals in Pensacola, Florida | 1418 |
| Orange Beach East Vacation Rentals in Pensacola, Florida | 1281 |
| Downtown Vacation Rentals in Pensacola, Florida | 281 |
| Southeast Pensacola Vacation Rentals in Pensacola, Florida | 198 |
| Northeast Pensacola Vacation Rentals in Pensacola, Florida | 171 |
| Northwest Pensacola Vacation Rentals in Pensacola, Florida | 164 |
| Toilla Segunda Vacation Rentals in Pensacola, Florida | 161 |
| Villa Sabine Vacation Rentals in Pensacola, Florida | 63 |
| Villa Segunda Vacation Rentals in Pensacola, Florida | 58 |
| White Sands Vacation Rentals in Pensacola, Florida | 34 |
| Perdido Key Coves One Vacation Rentals in Pensacola, Florida | 29 |
| Navy Point Vacation Rentals in Pensacola, Florida | 26 |
| Innerarity Townhomes Vacation Rentals in Pensacola, Florida | 24 |
| Sugar Beach Vacation Rentals in Pensacola, Florida | 24 |
| North Northwest Pensacola Vacation Rentals in Pensacola, Florida | 228 |
| Seville Historic District Vacation Rentals in Pensacola, Florida | 1168 |
