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Holiday Rentals near Santa Rosa Island

Pensacola, Florida
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    Travellers to Pensacola are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 248 Rentals in Pensacola
    35.1 kilometres from Santa Rosa Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Great energy in home1 / 10
    (2)Excellent
    32.6 kilometres from Santa Rosa Island
    1 Bedroom, 2 Bathrooms, Sleeps 1 Quick View
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    Cozy Queen Master Suite 2/2.5 in 2Story Home Near Beaches Private Balcony1 / 20
    (3)Average
    30.4 kilometres from Santa Rosa Island
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    The Gathering House in Pensacola1 / 36
    (20)Excellent
    32.2 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    East hill cottage✨10 min to Downtown✨1 / 11
    (6)Very good
    30.5 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Family friendly one bedroom/one bath In Grand Caribbean East1 / 21
    (54)Excellent
    51.6 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Bright & Sunny Beach Colony Condo, Directly Beachfront Amazing Views!1 / 29
    (35)Excellent
    51.9 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cute Cottage Getaway Downtown!1 / 6
    (6)Excellent
    30.9 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    La Playa 1202- Beach Front Views with Luxurious Amenities!1 / 47
    (10)Excellent
    51.8 kilometres from Santa Rosa Island
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Beach Colony East 7A- Beach Front unit with large terrace & amazing views!1 / 29
    (28)Very good
    51.9 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    COZY HOME 20min from Beach, close to city !1 / 42
    (40)Excellent
    29.8 kilometres from Santa Rosa Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Beach Colony East 8C- Beach Front unit with large terrace & amazing views!1 / 30
    (8)Excellent
    51.8 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    An Invitation to OASIS Lavallet in Beautiful Pensacola for 6-10 ppl, 3 BR w/POOL1 / 44
    (6)Excellent
    28.2 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 11
    Fabulous East End Unit at Beach Colony Resort1 / 38
    (37)Excellent
    51.9 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Little Red House *Fall Retreat* *Downtown Events *1 / 10
    (19)Excellent
    30.6 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Beach Colony East 13C-Beach Front unit with large terrace & amazing view!1 / 37
    (7)Excellent
    51.8 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Downtown Dreams is now available in Historic North Hill1 / 22
    (6)Very good
    31.8 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    The 'Jesse', a 1903 cottage in Historic District of downtown Pensacola.1 / 20
    (83)Excellent
    30.2 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Enjoy spectacular views of sugar sand beach front from huge balcony1 / 47
    (76)Excellent
    51.9 kilometres from Santa Rosa Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Sandy Key 825- Beautiful 2 bedroom unit with breathtaking views!1 / 31
    (36)Very good
    51.6 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming ranch style home with a private patio in quiet neighborhood.1 / 25
    (11)Excellent
    31.6 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Amazing views - 18th Floor Penthouse - 2 BR / 2 BA - Beautiful decor1 / 48
    (60)Excellent
    51.8 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Vacation Paradise at Purple Parrot Resort  Relax at the Tiki Bar New on1 / 23
    (55)Excellent
    51.7 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Waterfront view- 2 bedroom 2 bath1 / 22
    (47)Excellent
    46.2 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Family home , Large salt water pool (not heated) and tropical courtyard1 / 21
    (30)Excellent
    29.9 kilometres from Santa Rosa Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    **Coastal Luxury & Comfort**  Best location1 / 41
    (18)Very good
    32.3 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Downtown Dreams now available in Historic North Hill1 / 22
    (16)Very good
    31.8 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Snowbird-friendly condo w/ a shared pool - just moments away from the beach!1 / 48
    (20)Very good
    51.7 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Home near Perdido keys with pool in Pensacola 1.7m from beach. Near NAS1 / 47
    (61)Very good
    46.6 kilometres from Santa Rosa Island
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
    BEACHES OPEN, BLUE SKIES AWAIT!!!!! COME ENJOY THE SUNSHINE!!!1 / 26
    (61)Excellent
    51.6 kilometres from Santa Rosa Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Poolside unit! Book now for Summer 20201 / 24
    (18)Excellent
    51.6 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Beachfront Condo - Rental includes Ground Floor Storage for Beach Gear1 / 27
    (50)Excellent
    51.6 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Banana Bay 6083 Townhome - Waterfront + Fab Views & Amenities!1 / 45
    (14)Excellent
    51.8 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Rated #1(VRBO) Includes ground floor storage stocked with chairs and umbrellas.1 / 31
    (78)Excellent
    51.6 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    East Hill cottage retreat, perfect for couples, newly renovated1 / 31
    (73)Excellent
    30.3 kilometres from Santa Rosa Island
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    (PRIVATE ENTRANCE AND UNIT) PGS is Dog Friendly & 4 min from Downtown bars, art,1 / 14
    (10)Very good
    32.8 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Updated Gulf Front Beach Colony End Unit- Spectacular Views, Book Today!1 / 31
    (17)Very good
    51.8 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    BEACH FRONT PARADISE - 4 bedroom - Gated Community - witih Opt. 30 ft Boat Slip1 / 39
    (63)Excellent
    51.8 kilometres from Santa Rosa Island
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Snowbird-friendly w/ shared pool & beautiful ocean views - walk to the beach!1 / 35
    (29)Very good
    51.7 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
    Executive Style Florida Home looking for a Family***FREE HIGHSPEED WI-FI & Cable1 / 18
    (14)Excellent
    35.9 kilometres from Santa Rosa Island
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    The grass is greener on this side of the fence.1 / 32
    (8)Very good
    31.0 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Terrace
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Posh Beach Colony Penthouse- Beach Chic Decor & Direct Gulf Views!1 / 29
    (18)Excellent
    51.8 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Beach Colony East Penthouse 16B-Beach Front unit with amazing views!1 / 48
    (7)Excellent
    51.8 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Beach Colony Resort Gulf Paradise 10th Floor1 / 36
    (49)Excellent
    51.9 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pensacola, Florida Panhandle
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Amazing pool home on the Gulf Coast1 / 23
    (33)Very good
    21.5 kilometres from Santa Rosa Island
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
    A beach themed studio apartment that sleeps up to 41 / 9
    (4)Average
    35.5 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Gorgeous carriage house close to everything!1 / 27
    (91)Excellent
    29.3 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Slow Mo 17AD-Beautiful Beach Cottage * the Purple Parrot Resort/Perdido Key FL1 / 42
    (94)Excellent
    51.5 kilometres from Santa Rosa Island
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pensacola, Florida Panhandle
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    You Can Be One of Our 1st Guests to Experience Our Renovations & Updates!1 / 48
    (103)Excellent
    51.5 kilometres from Santa Rosa Island
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pensacola, Florida Panhandle
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    New Retreat ,  FREE Bikes,  Walk to everything ! Enhanced Cleaning1 / 47
    (25)Excellent
    31.5 kilometres from Santa Rosa Island
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
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    Pensacola, Florida Panhandle
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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