Santa Rosa Island Vacation Rentals

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Our top choices for Santa Rosa Island vacation rentals

Islander Beach Resort 504 Condo

Islander Beach Resort 504 Condo
3.0 star property
Okaloosa Island
The price is CA $378
CA $893 total
includes taxes & fees
May 3 - May 4
Islander Beach Resort 504 Condo

Baywatch F-3

Baywatch F-3
4.0 star property
Pensacola Beach
Baywatch F-3

Pensacola Beach Home: 1 Block to Beach Access

Pensacola Beach Home: 1 Block to Beach Access
3.0 star property
Toilla Segunda
10.0 out of 10, Exceptional, (2 reviews)
The price is CA $169
CA $527 total
includes taxes & fees
Apr 30 - May 1
Pensacola Beach Home: 1 Block to Beach Access

5 Portofino 1106

5 Portofino 1106
4.0 star property
Pensacola Beach
8.4 out of 10, Very good, (6 reviews)
"Very nice Unit . Definitely would stay again. "
United States
Doug
The price is CA $255
CA $1,275 total
includes taxes & fees
May 13 - May 14
5 Portofino 1106

2 Portofino 1602

2 Portofino 1602
4.0 star property
Pensacola Beach
The price is CA $514
CA $1,567 total
includes taxes & fees
May 6 - May 7
2 Portofino 1602

Seacrest 211 2 Bedroom Condo by RedAwning

Seacrest 211 2 Bedroom Condo by RedAwning
3.5 star property
Okaloosa Island
The price is CA $412
CA $1,127 total
includes taxes & fees
May 3 - May 4
Seacrest 211 2 Bedroom Condo by RedAwning

Golf Cart + Elevator: Retreat 1 Block to Beach

Golf Cart + Elevator: Retreat 1 Block to Beach
3.0 star property
Villa Primera
The price is CA $508
CA $1,562 total
includes taxes & fees
May 1 - May 2
Golf Cart + Elevator: Retreat 1 Block to Beach

1 Portofino 1005

1 Portofino 1005
3.5 star property
Pensacola Beach
7.4 out of 10, Good, (8 reviews)
"Expensive for what the place offers. WiFi doesn’t exist on this particular unit, we have to use public WiFi, when I called the front desk, I was advised to reach out to either Expedia or hosteeva since they’re the once I booked with, what a disappointment. Positive feedback, it’s complete with kitchen utensils, pots & pans, clean unit. "
United States
Dale
The price is CA $287
CA $1,311 total
includes taxes & fees
Apr 26 - Apr 27
1 Portofino 1005

Islander Beach Resort 403 Condo

Islander Beach Resort 403 Condo
3.0 star property
Okaloosa Island
The price is CA $314
CA $810 total
includes taxes & fees
Apr 19 - Apr 20
Islander Beach Resort 403 Condo

Sea La Vie Condo: Pensacola Beach Access!

Sea La Vie Condo: Pensacola Beach Access!
4.0 star property
Villa Sabine
10.0 out of 10, Exceptional, (3 reviews)
"It was perfect for a girls trip!"
United States
Wendy
The price is CA $161
CA $409 total
includes taxes & fees
Apr 26 - Apr 27
Sea La Vie Condo: Pensacola Beach Access!

Seacrest 206 is a gorgeous Gulf Front2 BR with Free Beach Service for 2 by RedAwning

Seacrest 206 is a gorgeous Gulf Front2 BR with Free Beach Service for 2 by RedAwning
3.5 star property
Okaloosa Island
Seacrest 206 is a gorgeous Gulf Front2 BR with Free Beach Service for 2 by RedAwning

Seacrest 701B is a 2 BR Gulf Front on Okaloosa Island by RedAwning

Seacrest 701B is a 2 BR Gulf Front on Okaloosa Island by RedAwning
3.5 star property
Okaloosa Island
The price is CA $583
CA $1,422 total
includes taxes & fees
May 8 - May 9
Seacrest 701B is a 2 BR Gulf Front on Okaloosa Island by RedAwning

Seacrest 404 2 Bedroom Condo

Seacrest 404 2 Bedroom Condo
3.0 star property
Okaloosa Island
Seacrest 404 2 Bedroom Condo

Recently renovated 2 bedroom/2 bath on 7th floor! by RedAwning

Recently renovated 2 bedroom/2 bath on 7th floor! by RedAwning
3.0 star property
Okaloosa Island
The price is CA $455
CA $1,201 total
includes taxes & fees
May 7 - May 8
Recently renovated 2 bedroom/2 bath on 7th floor! by RedAwning

701A is a Penthouse Effiency Gulf view unit on Okaloosa Island by RedAwning

701A is a Penthouse Effiency Gulf view unit on Okaloosa Island by RedAwning
3.5 star property
Okaloosa Island
The price is CA $455
CA $1,036 total
includes taxes & fees
Apr 17 - Apr 18
701A is a Penthouse Effiency Gulf view unit on Okaloosa Island by RedAwning

Seacrest 701AB is a 3 BR Gulf front on Okaloosa Island by RedAwning

Seacrest 701AB is a 3 BR Gulf front on Okaloosa Island by RedAwning
3.5 star property
Okaloosa Island
The price is CA $697
CA $1,836 total
includes taxes & fees
Apr 17 - Apr 18
Seacrest 701AB is a 3 BR Gulf front on Okaloosa Island by RedAwning

Islander Beach Resort 404 Condo

Islander Beach Resort 404 Condo
3.0 star property
Okaloosa Island
The price is CA $472
CA $1,084 total
includes taxes & fees
May 7 - May 8
Islander Beach Resort 404 Condo

Islander Beach Resort 303 Condo by RedAwning

Islander Beach Resort 303 Condo by RedAwning
3.0 star property
Okaloosa Island
Islander Beach Resort 303 Condo by RedAwning

Islander Beach Resort 302 Condo by RedAwning

Islander Beach Resort 302 Condo by RedAwning
3.0 star property
Okaloosa Island
The price is CA $316
CA $821 total
includes taxes & fees
Apr 30 - May 1
Islander Beach Resort 302 Condo by RedAwning

stayAPT Suites Pensacola-UWF/West Florida Hospital Area

stayAPT Suites Pensacola-UWF/West Florida Hospital Area
4.0 star property
Pensacola
9.2 out of 10, Wonderful, (262 reviews)
"Another awesome stay and pretty much my family’s exclusive accommodations when we visit Pensacola. Over 15+ trips in the past 24 months and only TWO stays somewhere else as they were sold out."
United States
Terrance Lamar
The price is CA $151
CA $170 total
includes taxes & fees
Apr 14 - Apr 15
stayAPT Suites Pensacola-UWF/West Florida Hospital Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Santa Rosa Island Hotel Reviews

Find out more about Santa Rosa Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Santa Rosa Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.