Guesthouse holiday rentals in Santa Rosa Island

Find and book unique guesthouse rentals on Airbnb

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Popular amenities for Santa Rosa Island guesthouses

Family-Friendly guesthouses

Top Guest favourite
Guesthouse in Pensacola
4.98 out of 5 average rating, 259 reviews

Pet Friendly, Pool, Hot Tub, Fenced yard.

WillRating, 5 stars2 months ago
The host's communication was amazing! Timely feedback and some great local recommendations. The property was perfect for a couple and the amenities are simply amazing. The pool and hot tub were a great addition and the only issue I have was I wish I could stay longer. The bed is comfy and the small kitchen was perfect for the space. Keep in mind the bathroom is small but completely manageable if you communicate with your travel partner. Easy to find and easy to access. Persons with mobility issues may have some difficulties navigating the stone pavers and the multi-level backyard. The kitchen also has two steps down from the main level of the studio. Bottom line…we loved it and think you will too! Time to stop reading and book before you miss your chance. I will 100% book again when I am in the area.
Guest favourite
Guesthouse in Destin
4.87 out of 5 average rating, 260 reviews

Crystal Beach carriage house

DruRating, 5 stars2 days ago
My wife and I had an amazing week long trip in Destin and this listing was a huge reason for it. The apartment was extremely clean, the kitchen was perfect and we had everything we needed. It was beautifully decorated too and the washer and dryer were so convenient!! The host was very kind and greeted us at check in. We preferred to go to Henderson State Park which was a 5 min drive over the beach down the street in the morning because it does seem to get crowded due to limited public space unless you get there super early. I will definitely be back if it is available. Thank you!!!!
Guest favourite
Guesthouse in Santa Rosa Beach
4.85 out of 5 average rating, 185 reviews

Carriage House 1.5 bed/1 bath located off 30A

WillRating, 5 stars1 week ago
This place lived up to high expectations, thoroughly enjoyed the stay, highly recommend especially with kids.
Guesthouse in Navarre
4.68 out of 5 average rating, 188 reviews

Guest House Suite & Pool Near the Beach!

CarolynRating, 5 stars4 weeks ago
Matthew was very hospitable and kind.communicated well with me upon arrival and departure. We enjoyed our stay and will return to the home as well as the area. We just went to relax and go fishing and to the beach. Plenty to do in the area also.
Guest favourite
Guesthouse in Pensacola
4.92 out of 5 average rating, 639 reviews

Cottage Under the Trees

ManiqueRating, 5 stars3 weeks ago
Larry & Kelly were truly amazing hosts!!! Everything listed on this app was exactly as such in the cottage we rented from them. Kelly greeted us in such a kind manner when we first arrived and was very welcoming. Both hosts were active in messaging us to see if we needed any extra toiletries or paper products and answering any questions we had about where to go while on our stay. The cottage was clean & provided everything we needed with no issues. Larry & Kelly helped make my honeymoon with my husband easier and extremely relaxing. Whenever we come back, it is our hope they will be available to book again! Wonderful home, lots of privacy, great hosts! 10/10 for my first time booking an AirBnB.
Top Guest favourite
Guesthouse in Pensacola
4.76 out of 5 average rating, 158 reviews

Private Pool House

KeithRating, 5 stars1 month ago
Me and my partner enjoyed our stay at the private pool house, it was quiet and peaceful and we get to spend some time together since we’re so busy with our work schedules. The home decor reminds us of being at an actual beach and basking in the sun. K is a very great and friendly host she’s was always there when we needed her and responds as quickly as possible.We would definitely stay here again in the future and would definitely recommend this place to anyone who wants to visit Pensacola.
Guest favourite
Guesthouse in Fort Walton Beach
4.87 out of 5 average rating, 321 reviews

➢ 30 Seconds to the Beach - Private Guest House! ☼

JoshuaRating, 5 stars1 week ago
Very beautiful place I will definitely be staying here again one I go on vacation. Chris was very friendly and quick to respond.
Superhost
Guesthouse in Seacrest Beach West

Happy Hour on 30A #5 | Steps from Beach | 4 Bikes

VickyRating, 5 stars47 months ago
Home was what we expected. Loved the location. Private entrance to beach, only down side was we still had to walk to public beach access couldn’t stay at the private beach area. Bike ride away to downtown Rosemary beach. Lovely restaurants and shopping centers. Disappointed with the cleanliness of the home, very dirty when we checked in floors hadn’t been swept or mopped, crumbs on counters and couch bathroom showers looked dirty. I had to wash was all the bed sheets they didn’t look clean. They sent over 2 lady’s to clean the house within a hour but they just swept the floors, Both ladies where walking around barefoot and had no mask on, I wasn’t happy. They did ask if I wanted anything else done before they left, by this time it’s almost 9pm and we where all tired from our drive in. I just wanted them to leave so we could rest. I would have been very happy if only it had been cleaned properly.

Guesthouses with a patio

Guest favourite
Guesthouse in Fort Walton Beach
4.92 out of 5 average rating, 96 reviews

Cozy 1-bedroom Guest House

JessicaRating, 5 stars4 weeks ago
Deion made us feel right at home and he was a great host! His place is extremely cozy and easily accessible. Thank you so much for providing a great space to unwind and enjoy the local surroundings. Definitely would stay again
Top Guest favourite
Guesthouse in Gulf Breeze
5 out of 5 average rating, 18 reviews

Two Air Bnb's + boat parking for 1 Great Price.

MakesiRating, 5 stars2 weeks ago
This stay was just what we needed. The place was spotless and looked exactly like the photos. Our host was amazing and very responsive. It felt cozy and made me feel right at home. The location is great—close to the beach and popular attractions. I enjoyed my time here and plan to return. I’ll definitely book again.
Top Guest favourite
Guesthouse in Gulf Breeze
5 out of 5 average rating, 25 reviews

Hummingbird Cottage

VeronicaRating, 5 stars1 week ago
I could not brag more about Sue and Dana’s lovely cottage! Very quiet and beautiful neighborhood close to the beach and nice local restaurants. Dana and Sue were very helpful and very welcoming, made us feel right at home when we showed up! Sue also made us the cutest home made cookies my kids loved them! 10/10 would recommend! We will most definitely be back!
Top Guest favourite
Guesthouse in Milton
4.99 out of 5 average rating, 144 reviews

Charming Bayou Bungalow near downtown Milton!

KathyRating, 5 stars2 weeks ago
Angela was great to deal with and so organized! The Bungalow was charming and the amenities was a nice addition!! Loved sitting at the dock with a nice cold beer! Highly recommend!
Guest favourite
Guesthouse in Pensacola
4.92 out of 5 average rating, 181 reviews

Cozy 1 bedroom East Hill Garage Apartment

VanessaRating, 5 stars2 weeks ago
Our stay was perfect. This was our second time at this residence and we loved it. It’s in a great location and close driving range to the beach. Perfect for 1-2 people!!
Top Guest favourite
Guesthouse in Navarre
4.98 out of 5 average rating, 85 reviews

Never Navarre From Home Cottage

BonnieRating, 5 stars1 week ago
Absolutely stunning 🤩 very clean. Kept great communication and always offered assistance if needed. Would definitely 💯 recommend to others. I love that the beach 🏖️ was just over the bridge. Close to everything and very private for bunking down for the night. Peaceful 😌 and quiet 🤫 😍. Thank you 😊
Top Guest favourite
Guesthouse in Pensacola
4.98 out of 5 average rating, 119 reviews

Spacious Guesthouse by Alga Brewery & Waterfront

MackenzieRating, 5 stars1 week ago
Abby’s place was in the perfect spot! Very quiet but also close to everything. All of the food was amazing especially the brown bagger food truck that’s within walking distance. The place itself was tidy and organized. Abby communicated very well and answered all of our questions. We had such a great time and loved our stay!
Guest favourite
Guesthouse in Elberta
4.95 out of 5 average rating, 152 reviews

Quaint Tiny Home by the Bay (Mini Cottage)

JermaineRating, 5 stars1 week ago
I enjoyed my stay. This place is great for a peaceful couples getaway or solo trip. The interior looked recently renovated. It was extremely clean and smelled great. The furniture was very comfy; especially the bed. I had all amenities I could need including an iron and ironing board. This was the first time I traveled with my dog. The space was pet friendly. The backyard was fenced in and had decent space for him to stretch his legs. The host was great with communication. He was proactive and responded swiftly when I sent a message. If you like peace and quiet and rural living this is for you. It’s a slight drive to the tourist areas which I personally didn’t mind. I’m retired military and travel a lot and I’ll be keeping this listing in my favorites.

Guest house rentals with a washing machine and dryer

Top Guest favourite
Guesthouse in Destin
4.98 out of 5 average rating, 375 reviews

Carriage House by the Beach

JennyRating, 5 stars2 weeks ago
Excellent stay! This location is ideal for a solo beach trip or for two adults! Check in was extremely smooth. Very comfortable mattress! Loved having access to the beach and beach chairs. Great location and beach in Destin! Would highly recommend to others!
Guest favourite
Guesthouse in Pensacola
4.92 out of 5 average rating, 105 reviews

Chic Studio in Historic Downtown Pensacola

TinaRating, 5 stars3 months ago
Great stay! Beautiful place with everything you could want or need. Would highly recommend!
Top Guest favourite
Guesthouse in Santa Rosa Beach
4.98 out of 5 average rating, 110 reviews

Cypress Key

KristiRating, 5 stars2 months ago
Loved this place! Clean coastal decor. Beautiful quiet setting. Wonderful amenities. Enjoyed biking, walking, playing pickleball and using the weight room, and especially loved the large infinity pool. Great area on 30a as it’s close to beach and good restaurants like Stinky’s.
Superhost
Guesthouse in Santa Rosa Beach
4.82 out of 5 average rating, 224 reviews

Santa Rosa Beach Tiny House

BenRating, 5 stars1 month ago
Cheri's place was fantastic! Great location, great communication. Would highly recommend this Tiny House!
Top Guest favourite
Guesthouse in Pensacola
4.98 out of 5 average rating, 120 reviews

The Paradise Cottage-clean+gated

AprilRating, 5 stars2 weeks ago
We loved our stay here . Anita is awesome !! Everything was clean ,easy checkout, so comfortable. The cottage was gorgeous 🩷
Top Guest favourite
Guesthouse in Gulf Breeze
4.99 out of 5 average rating, 107 reviews

Summer Paradise Getaway

MaryRating, 5 stars3 days ago
We really enjoyed our vacation at John David’s pool house this week. For the first two days of our stay the pool came in clutch since there was a jellyfish warning at the beach. It was the perfect size for my family of 3. Very clean, had everything we needed with great personal touches, like board games, cards, a box of hot tea in the pantry. Speaking of the kitchen, John David thought of everything we could need - and then some! We usually eat at the airBNB two meals per day, and the cabinets were stocked full of pots, pans, measuring cups, etc that made making meals a breeze. I can see why this property is a fan favorite! It’s easily one of my family’s favorites too!
Top Guest favourite
Guesthouse in Santa Rosa Beach
4.97 out of 5 average rating, 239 reviews

Dune Villa - Santa Rosa Beach /30-A

LorenaRating, 5 stars2 weeks ago
Such a great place to stay! Will definitely stay here again.
Top Guest favourite
Guesthouse in Pensacola
4.96 out of 5 average rating, 100 reviews

East Hill Retreat/Pet Friendly

AlanRating, 5 stars1 week ago
We loved our stay! Everything we needed and close to everything. The amenities were above and beyond. We left our crock pot at home but were delighted to find she had one in the shelf. Nothing better than coming back to a shrimp boil after a day at the beach. Definitely one of the premiere Airbnb hosts in Pensacola!

Destinations to explore