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Holiday Rentals with Pools in Pensacola

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    Travellers to Pensacola are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    59 Matching Rentals in PensacolaView all 91 rentals
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    ROMANTIC Beach Getaway for Couple!1 / 45
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet-friendly Apartment with pool, hot tub & boat ramp near Pensacola Beach1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    $199/night  Brand New Interior, many upgrades1 / 23
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    • Cable/satellite TV
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    • Washer
    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Charming 2 BR on Old River in Perdido Key with assigned Boat Slip! This 3rd-floor condo has wonderful views of the Gulf of Mexico from the Front Balcony and Kitchen door. The Main Living area and Master Bedroom have the ever entertaining boating activity on Ole River! The Condo is Located only 1.5...
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Yosanmine 10ad1 / 10
    (22)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beachcomber Bliss 38c1 / 22
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Esta 11bd1 / 16
    (20)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Parrot-dise 13au1 / 11
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tropical Therapy 5cu1 / 11
    (20)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Belize Place 4c1 / 16
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rancho Deluxe 27cu1 / 16
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    • Hot Tub
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    Pet friendly
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Purple Parrot 18cu1 / 12
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Lazy Daze 10au1 / 26
    (29)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean Melodies 10b1 / 17
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea La Vie 2cd1 / 10
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perdido Sun Resort 9121 / 11
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Andalucia 16c1 / 18
    (19)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Hot Tub
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    Pet friendly
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Slow Mo 17ad1 / 12
    (28)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perdido Sun Resort 7061 / 15
    (30)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Reviewed 18 August 2015
    Great location with spectacular views of the Gulf of Mexico. Condo has everything you need for a quiet vacation. Great bed. Publix and Winn-Dixie about 1 mile away. National...
    Reviewed 4 June 2015
    We love Perdido area and Perdido Sun. Great location, front desk helpful, facilities and condo 706 super. Not so thrilled with agency handling 706 for owners. Wrong info re...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Serenity Now 13ad1 / 12
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Parking
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    Pet friendly
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    Smoking allowed
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    The Parrot Perch 6au1 / 26
    (23)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Hakuna Matata 23c1 / 19
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cozy Hideaway 22c1 / 15
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
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    Pet friendly
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    Smoking allowed
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bahama Mama 18cd1 / 12
    (33)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Dues Paid 32c1 / 19
    (19)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Perdido Skye Resort 531 / 16
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Reviewed 9 July 2013
    I stayed here back in May. The place was perfect for a family of four. Our ten year olds especially enjoyed the bunk beds and the master bedroom was huge! Any and everything we...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Life's A Beach 15a1 / 20
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Seaclusion 18a1 / 20
    (31)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Colony Resort Gulf-Front Condo – Breathtaking Views!1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool (Unheated)
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    • Wi-Fi
    • DVD Player
    • Hot Tub
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    Pet friendly
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    Smoking allowed
    About this property
    Everything you’ve been dreaming of for your beach vacation is reality at Beach Colony Resort, a luxury getaway loaded with amenities. At our 2BR/2BA condo, you’ll soak up picturesque views of sandy shores from nearly every room and feel the Gulf of Mexico breeze on your private balcony. Onsite...
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Boogie Man 36c1 / 19
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coastal Escape 17c1 / 21
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perdido Sun Resort 7041 / 22
    (20)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perdido Sun Resort 1108 by PKRM1 / 20
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Reviewed 17 June 2018
    Lovely week on this ocean front condo! Pictures are accurate. Everything you need in condo. Extra details not in other reviews: Each bedroom has direct access to the bathroom...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Caribbean Soul 40c1 / 32
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    Pet friendly
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    Reviewed 7 October 2015
    I don't think it can get much better than 40C at the Purple Parrot. The location is secluded and quiet, but a short walk to the pool and Tiki Bar. The owners have obviously...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mer'sea 21c1 / 24
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Perdido Sun Resort 308 by PKRM1 / 21
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Southern Grace 34cd1 / 15
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Parrot Bay 37cu1 / 14
    (10)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Sea Robin 11A1 / 24
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Perdido Sun Resort 10061 / 9
    (31)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Shared Indoor Pool
    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome to the most luxurious and spacious condo in the absolute best location in Orange Beach. This condo features 3,400 square feet inside and a wrap around 1,800 square foot balcony that circles the condo. Every bedroom had balcony access. This unit can easily and comfortably handle a large...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious condo is approximately 3500 sq.ft. with spectacular views of the gulf and wraparound balcony. It features a gourmet kitchen with wine cooler, double-sided sub-zero refrigerator, and stainless steel appliances. The master bedroom is located oceanfront and is quite spacious with floor...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Caribbean Queen 28cd1 / 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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