
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Santa Rosa Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Free Chair Service-Beachfront 6th Floor
Beautiful sixth-floor balcony views of beachfront, barrier island chain, and sound area! Exceptionally convenient white-sands beach access and gorgeous emerald waters! Enjoy the indoor/outdoor pool and on-site gym. This beach condo is not only fantastically located on the quieter end of Okaloosa Island, but also comes with modern, coastal-themed furnishings. Access the Destin and Fort Walton Beach attractions only a few miles down the street. Includes free chairs and umbrella on the beach!

Relaxing Soundside Condo - WataView!
Vacation or work at our comfortable waterfront kitchenette studio in the heart of Fort Walton Beach. The sugar white sand beaches are just a short drive away, and adventure awaits right at your doorstep on Santa Rosa Sound. Includes pool and marina! Boat slip (28 Ft) available! The unit has a queen bed and futon that lays down to a full size bed. It's very comfortable for small groups. We are real owner-hosts and strive to keep our unit spotless and well supplied for our cherished guests.

Spacious, elegant, beachfront, w/office
* Huge oceanfront lanai * Free beach service April 1-Oct 31 *Adult/Kiddie pool; tennis *Private office space in the condo *High chair/pack-n-play *Huge 1453 sq ft *Fully stocked kitchen incl. air fryer *Near Destin but WAY less crowded *South facing for sunrise & sunset (seasonal) & sometimes dolphins! *Open the door to your private lanai for REAL white noise of the ocean waves

Beachfront Bliss! Gulf Waves at The Palms #201
Nestled on the shimmering shores of the Gulf, The Palms #201 invites you to unwind with jaw-dropping oceanfront views and the gentle lullaby of waves kissing the coast—pure paradise at your doorstep! This 2-bed, 2-bath sanctuary is your ticket to an unforgettable coastal retreat, blending relaxation and rejuvenation. Steps from the Gulf’s sparkling waters, this guest-favorite escape promises a home-away-from-home experience that’ll leave you dreaming of your next stay.

Kid-friendly! Lazy River~Skywalk over to beach!
This is a beautiful one bedroom condo plus bunk area located on Bayside of Destin West! The unit comes equipped with a beach cart to make the short walk to the beach even easier! You will love the location of this unit! Freshly painted, with beautifully decor, plus beach towels (2) - you will feel right at home at our 'Salty sandpiper'. With a fully stocked kitchen, washer and dryer, and a lazy river pool - this condo is the perfect place for your beach getaway!

Perfect View on Santa Rosa Sound with 2 Pools!
Enjoy beautiful blue skies and gorgeous sunsets over the Santa Rosa Sound, while looking out over the marina from your very own private deck! This gorgeous studio unit has one of the best views in the entire 120 room complex! Located in the preferred A building, this Non-Smoking, NO PETS ALLOWED, sparkling clean top floor unit has a beautiful bathroom with full size tile shower and newer plumbing fixtures. Marina slip is not available for rent at this time.

Sunshine and beach time /Okaloosa Island
CHRISTMAS at the BEACH! Steps to the sand, Ocean view , top floor unit, sleeps 5,(queen bed, single day bed, and queen sofa sleeper). Fully furnished, ( USB port outlets, no carpet, stainless appliances, and keyless entry). A one minute walk to the white sand, wifi in the unit, 2 beach chairs, cooler, beach towels, and beach umbrella. Laundry onsite, Tom Thumb next door for items you might need. Everything for a great beach vacation! 683 Nautilus court

Bay View Studio Condo
This nicely styled studio condo has an amazing view of the bay and the pool from the balcony. This studio Condo sleeps 2 guests very comfortably but for small families and small groups trying to save, we have a futon couch and can fit up to 4. Condo has a pool on site and also has a washer and dryer on the same level near the elevator. Within 5 minutes from downtown Ft. Walton Beach with Plenty of restaurants and other attractions near the condo.

Gulf View Studio condo Fort Walton Beach
Islander 705 Studio condo with a beautiful Gulf view on Okaloosa Island. This 7th floor unit sleeps 2 and includes - 1 King bed - 1 sofa sleeper - 1 Full bathroom (glass shower) - Keurig Mini - 1 full kitchen with stove, refrigerator, microwave, dish washer Complimentary beach service 2 chairs and 1 umbrella included March - October! Enjoy BREATHTAKING views of the Gulf & white sand beaches with the perfect sunset view from the balcony!

Emerald Waters & Sugar White Sand!
Enjoy all the comforts of a North American lifestyle with a modern contemporary look and stunning Gulf-front views from our high-floor corner unit. Located right on the beach with no roads to cross and close to Destin. High-speed Wi-Fi, keyless entry, smart TV, beach towels, starter amenities, a seasonally heated Gulf-front pool (March 1–April 30 & Oct 1–Dec 31, subject to change) and MORE. Have a sunny day!

"The Golden Sun" condo
"The Golden Sun." A luxury and calm stay in a 4th-floor condo only steps from the beach. Enjoy golden sunsets from the balcony that oversees the beach! Fast wifi with Alex integration(not offered by most condos). This features 1 bed and 1 sofa bed for a 4 person stay. 2 full bathrooms. A nice small kitchen so you can cook! Two TVs with Rokus for streaming. Small community grills for BBQ and a beautiful pool!

Beachfront! Sand-Sun-Surf on Fort Walton Beach FL
Relax and getaway to this beachfront condo retreat on Okaloosa Island in Fort Walton Beach, Florida. Just steps to the sugar-white sand and emerald Gulf coast waters, this updated 2BR/2BA condo features a private balcony with dolphin & sunset views, modern kitchen, Wi-Fi, washer/dryer, and pool (heated in the winter). Free beach service (2 chairs + umbrella, Mar–Oct). Only 5 miles to Destin!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Destin Retreat: Oceanview Poolside Luxury Condo

5 Min Walk to Beach, Pool, Loaded Game Room !

Sugar Sand Cottage at Destin Pointe

Private Heated Pool! Walk 2 Beach!

Waterview Villa-Steps to the Sand-Pool-King Bed

Fall Now Open! 1 Block to Beach + Pool • Sleeps 16

FREEGolfCart!/HEATEDPool!/Walktobeach! Sleeps 10!

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A
Condo rentals with a pool

Nautilus 1206 Gulf Front 2 BR/2 BA 2nd FL. Free B

Majestic Sun A603*5 Beds*Heated Pools&Hot Tubs*Gym

"SeaGlass" - Oceanfront with expansive balcony.

Sleeps 4•Waterfront•Pet Friendly•2.5 Miles to Gulf

Sunrise Destin-ation -Heated Pool-Beach View

Beachfront 1 BR 10th Fl. at Pelican, Amazing Views

Beach Side 1/1 Condo Paradise

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach
Other vacation rentals with a pool

Beach Front Penthouse, Stay Salty, Free Activities

DW Osprey PH03 ~ Penthouse ~ Hot Tub ~ 360° Views

Gulf Front #2002 ETW 3King /3Bath Renovated

B210 Pirates Plunder

Gorgeous Gulf Front condo with amazing views!

*Luxury Baytowne Wharf- Bahia Breeze* w/Pool View

Penthouse Paradise on Okaloosa Island

Gulf View Island Studio w/ Restaurant Nearby
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $215 CAD | $230 CAD | $303 CAD | $314 CAD | $321 CAD | $397 CAD | $513 CAD | $342 CAD | $298 CAD | $270 CAD | $220 CAD | $212 CAD |
| Avg. temp | 12 °C | 14 °C | 17 °C | 20 °C | 24 °C | 28 °C | 29 °C | 28 °C | 27 °C | 22 °C | 16 °C | 13 °C |
Quick stats about vacation rentals with a pool in Santa Rosa Island

Total vacation rentals
Explore 2,550 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at $70 CAD per night before taxes and fees

Verified guest reviews
Over 55,400 verified reviews to help you choose

Family-friendly vacation rentals
1,850 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
1,680 properties have a dedicated workspace

Wifi availability
2,550 of Santa Rosa Island vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Santa Rosa Island rentals

4.7 Average rating
Santa Rosa Island stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Santa Rosa Island’s top spots, include Destin Harbor Boardwalk, Crab Island, and Gulfarium Marine Adventure Park
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- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Destin Harbor Boardwalk
- Crab Island
- Princess Beach
- Frank Brown Park
- James Lee Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Blue Mountain Beach
- Grayton Beach State Park
- Tiger Point Golf Club
- Pensacola Beach Crosswalk
- Eglin Beach Park
- Raven Golf Club
- Gulfarium Marine Adventure Park
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access
- Camp Helen State Park
- Pensacola Dog Beach West
- The Track - Destin
- Fred Gannon Rocky Bayou State Park
- Seacrest Beach
- Shipwreck Island Waterpark
- Wayside Park, Okaloosa Island
- Gulf World Marine Park