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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 home today, and have the perfect trip.
    63 Matching Rentals in PensacolaView all 88 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pool house with water views & boat launch! Sleeps 4 adults comfortably, but can squeeze a total of 7. “Premier All Included” DirecTV package, Netflix & fast internet! The kitchen and bathroom are fully equipped. The bedroom has a king memory foam mattress. The living room sofa pulls out to a queen...
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    Pensacola, Florida Panhandle 32563
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
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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
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sea La Vie 2cd1 / 10
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 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 - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • DVD Player
    • Sauna
    • Air Conditioning
    • Internet Access
    • Hot Tub
    • Shared Indoor Pool
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2018
    We just left and are ready to go back!! Jill was amazing, the cottage felt like home she had everything that you could possibly need. This was a short getaway for my husband and...
    Reviewed 20 September 2017
    We thoroughly enjoyed our stay! We could not have asked for better accommodations! Loved the cottage, such a quaint place for a getaway. Will definitely return!!!
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    About this property
    Dreaming about a get-away to the beautiful sugar-white sand beaches of Perdido Key? Plan a romantic weekend at 'The Sand Dollar' beach cottage. Stay at a 1 bedroom cottage villa at Purple Parrot Resort, a 10 acre tropical resort with hundreds of palm trees, all nestled around a 5,000 square foot /...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    • Private Outdoor Pool (Heated)
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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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    Hakuna Matata 23c1 / 19
    (32)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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    $199/night  Brand New Interior, many upgrades1 / 23
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    This was the perfect getaway spot. Didn't need to leave the condo for beach activity. Water was right in the backyard! Great scenery! I look forward to going back!
    Reviewed 10 April 2017
    This is my best experience renting a place to stay. The communication with the owner was a top notch. The place is completely private. The apartment was spotless when we...
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    About this property
    Great family vacation spot. The kids can play in the shallow water beach as the adults supervise from the shaded balconys off the unit. Take the Kayak out for a paddle, enjoy the beautiful pool over looking Perdido Bay. This is truly a relaxing spot away from all the hustle and bustle. Bring your...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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 32501
    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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    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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    Beachcomber Bliss 38c1 / 22
    (22)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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    1 Bedroom, 1 Bathroom, Sleeps 4 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 - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, 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)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    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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    Parrotopia 2b1 / 17
    (27)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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    Serenity Now 13ad1 / 12
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 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 - 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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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    Reviewed 17 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 3 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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    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)
    • Parking
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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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    Southern Grace 34cd1 / 15
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • 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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    Coastal Escape 17c1 / 29
    (16)Very good
    3 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 - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    Mer'sea 21c1 / 24
    (15)Excellent
    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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    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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    Purple Parrot 18cu1 / 12
    (15)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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    Perdido Skye Resort 531 / 16
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
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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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    Seaclusion 18a1 / 20
    (31)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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    Slow Mo 17ad1 / 14
    (28)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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    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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    Boogie Man 36c1 / 19
    (16)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 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 8
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    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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    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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    Parrot Bay 37cu1 / 14
    (10)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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    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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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
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    • Balcony
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect beach getaway, look no further than this 2-bedroom, 2-bathroom vacation rental condo in Pensacola. Located just steps from Johnson Beach, this recently renovated corner unit for 8 is private, peaceful, and of course beautiful. Complete with access to a heated pool,...
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Paradise Found 10c1 / 28
    (26)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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    Perdido Skye Resort 251 / 14
    (3)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Reviewed 13 February 2015
    We were disappointed in this unit but it is "ok" and the price is right. We talked with the management company and gave them a list of things that would improve the...
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach Colony East 1B by PKRM1 / 12
    (17)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 306 by PKRM1 / 6
    (21)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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    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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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Bahama Mama 18cd1 / 15
    (33)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Parking
    • 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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    Ocean Melodies 10b1 / 17
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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