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Holiday Rentals with Pools in Pensacola

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    $239 Average
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    Travellers to Pensacola are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    13 Matching Rentals in PensacolaView all 41 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 pool house with boat ramp near Pensacola Beach1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Washer
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2018
    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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    Beach Colony Resort Gulf-Front Condo – Breathtaking Views!1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    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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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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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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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 1 bedroom 1 bath downstairs condo at the Purple Parrot Village Resort located in a secluded area of the resort. This condo comfortably sleeps a family of no more than 2 adults. The living room is equipped with a television, DVD player, and internet but does not offer a sleeper sofa....
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    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a 3 bedroom 2 bath privately owned vacation home at the Molokai Villas complex located directly on the beach side of Perdido Key Drive. This vacation home condo comfortably sleeps a family no more than 8 including all adults and children. There is a large balcony facing the beach which is...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Terrace
    • Grill
    Suitability
    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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    Location Information
    Pensacola, Florida Panhandle 32507
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    SPECIALS! $795 Wks!PIER WATERVIEW POOL NR PRIVATE BEACHES! PET FRIENDLY!NR NAS!1 / 49
    (29)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    A very pet friendly cozy place to stay. The owner is very easy to work with and follows through to make sure everything is what you were expecting. Everything one could need...
    Reviewed 29 September 2017
    I loved my time in Pensacola! Beautiful city and lovely, relaxing beach! Renting this space really made my stay! Clean and inviting. Spacious kitchen and two bathrooms! It was...
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    About this property
    SPECIALS and this is the best part of Summer low rates warm weather no tourists! $795 - $895!Weeks FOR A LIMITED TIME and $150 nights min. 3 nights (Some dates in September, all of October and November! This is for up to 4-5 guests)Book Now for Labor Day Week or Weekend!*!Ad does not always reflect...
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    Location Information
    Pensacola, Florida Panhandle 32507
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your Florida getaway begins at the 'Pensacola Retreat,' a 2-bedroom, 1.5-bathroom vacation rental home for up to 5 guests. This prime location is just 15-20 minutes from the beach and a quick walk to the Bay. Lounge poolside at home or venture out to watch the Blue Angels and grab a bite to eat at...
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    Location Information
    Pensacola, Florida Panhandle 32504
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for a long term or short term snow-bird getaway, this 2nd-floor vacation rental apartment boasts new updates and a home-away-from-home experience in the western Florida panhandle. With room for 3 guests, you'll have access to a shared in-ground pool, patio, bicycles, beach equipment, and...
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    Location Information
    Pensacola, Florida Panhandle 32504
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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