
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.

Waterfront cozy condo with king bed & resort pool
Welcome to The Salty Pirate, your waterfront vacation paradise! Kick back & relax in our calm, stylish condo featuring a king size bed, luxury bathroom & kitchenette. Relax in bed, enjoy the boats cruise by or watch the 65 inch TV. The waterfront balcony entices you to read & relax. Enjoy the resort style pool or reserve the 2-seater kayak (when available) provided for you to explore the waterway. Downtown restaurants & bars are walking distance & the white sugar sand beaches are 2 miles away!

Destin West, Bayside, 2 BR+ Bunk Room, sleeps 8
GREAT VIEWS!!! Sandpiper unit 502 has 2 bedrooms, two baths, and a private bunk-bedroom, so its really a 3 BR...sleeps 8. It is furnished with a new sofa sleeper and matching couch in family room. All of this is designer furnished condo accommodates up to eight people to sleep. The interior of the unit reflects a classic, high-end feeling. Walking distance to many restaurants and activities. My place is close to restaurants and dining, the beach is 5 minute away over elevated walkway, .

Beachfront! Newly remodeled! Right on the beach!
Beachfront top floor unit, on a private beach, in two story building gives unobstructed sunset/ocean views. Located on soft white sand with on-site free parking. Perks of choosing this unit include gated resort with pools, beach service included (Mar.-Oct.), tennis courts, pickle ball, and par 3 golf course (included). Unit has fully functional kitchen and wifi included. Master bedroom beach/sunset views! Sleeps 4 adults with use of sofa bed in living area and additional cot-sized bunkbeds.

Oceanfront 3BR/3BA Condo | Steps to Sand & Surf!
Experience the Gulf in a Newly Remodeled Condo! This family-friendly ground-floor unit offers ultimate convenience. The master bedroom has ocean views, a king bed with a pullout trundle. The second bedroom has a king bed with a trundle, and the third has a queen bed. The living room includes a queen sofa bed. Each bedroom has a private bath and TV. Enjoy free beach service March–Oct with two chairs & an umbrella. Step onto the sand, relax, and unwind! Guests 27+ only. No smoking. No parties

Cozy Soundside Condo - WataView2!
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.

One Step to the Beach!
"One Step to the Beach" Highlights: - Beachfront Condo at Surf Dweller - First Floor - Pull Up to the Front Door and Unload - Free “Platinum” Beach Service: 2 Beach Chairs, Umbrella + Kayak / Paddleboard access (Mar-Oct) - Two Parking Spaces - 1 King Bed - Master Suite - 2 Queen Beds - Second Bedroom - Cable + Streaming - WiFi - Keurig and Drip Coffee Makers - Seasonal Heated Pool - Tennis/Pickleball Courts - Washer and Dryer in the Condo - Pack n' Play - Shopping / Restaurants Nearby

Sunrise Destin-ation -Heated Pool-Beach View
“Sunrise Destin-ation” is the perfect spot for your next Destin getaway! “5-10 minutes away from everything - from the Beach, across the street, to limitless restaurants. Prime location for a trip to Destin!” – Cordelra, ‘23.. Our freshly remodeled condo, with a king bedroom, a twin-bunk alcove, and a queen sleeper sofa accommodates up to 6 guests easily so indulge in our community pool just STEPS from 2 gorgeous public beach access points directly across the street. Enjoy!

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

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 amazing views of the Gulf & white sand beaches with the perfect sunset view from the balcony!

Island Princess 618 | Gulf Views & Beach Service
Experience the ultimate beach getaway at our renovated condo on stunning Okaloosa Island. This beachfront retreat features two spacious bedrooms, two modern bathrooms, and a rare oversized balcony perfect for soaking in the breathtaking views. Relax on the sugar-white sands and take in the emerald-green waters of the Gulf with complimentary beach service, including two chairs and an umbrella, provided from March 1st to October 31st.

Sea Shell at Sunset Cottages - Beach Service Inc
Sea Shell condo is located in the 19 unit Sunset Cottages complex on Okaloosa Island in Fort Walton Beach, FL. “Gulf Side”, just over 200 steps from the sand, no roads to cross, relaxing on the beach in minutes! The Sea Shell has 2nd floor partial gulf views from the dining room window, and both balconies. Inside is a spacious 750 sq.ft. to lounge and relax including; large great room, large bedroom and bath, condo built in 2000.

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!
Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Santa Rosa Beach Canopy House with heated pool

Sugar Sand Cottage at Destin Pointe

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

Oceanview | Pool | Private Beach | Golf Cart

Saltwater Pool Firepit & BBQ Pet-Friendly Near 30A

Fresh Fun Interior | New Golf Cart | Heated Pool

#1 4BR HUGE PET Friendly Home Away from Snow!

Saltwater Pool/Spa, Cali King, BBQ, BEACH 4-miles
Condo rentals with a pool

Spacious, elegant, beachfront, w/office

Beach Penthouse on Okaloosa Island in FWB, FL

Beachfront 30A Private Beach Blue Mountain Paradis

Destin West V506 - Free Beach Service & Lazy River

The Lovers’ Escape 229

Star Of The Sea

Zen Retreat ON Beach -Golfcart* Hot Tub, SanDestin

Beach Side 1/1 Condo Paradise
Other vacation rentals with a pool

Summer breeze house with beach view

Pool Table, Lazy River & AmazingViews! Destin West

3BR Oceanfront 3rd-Floor | Balcony | Pool

314 Island Princess - Beach, Pool, Spa, Balcony!

"SeaGlass" - Oceanfront with expansive balcony.

Destin West Villa PH04~ Hot Tub,on Rooftop Terrace

Emerald Coast Retreat

Summer Place 501 - 3Bd Beachfront Condo - 2 Sets o
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 | G$32,206 GYD | G$34,506 GYD | G$45,381 GYD | G$47,054 GYD | G$48,099 GYD | G$59,601 GYD | G$63,784 GYD | G$44,962 GYD | G$39,734 GYD | G$40,362 GYD | G$33,042 GYD | G$31,787 GYD |
| 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 G$10,456 GYD 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 110 rentals that welcome pets

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

Wi-Fi availability
2,550 of Santa Rosa Island vacation rentals include wi-fi 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
Destinations to explore
- Seminole Vacation rentals
- Florida Panhandle Vacation rentals
- Atlanta Vacation rentals
- New Orleans Vacation rentals
- Panama City Beach Vacation rentals
- Destin Vacation rentals
- Jacksonville Vacation rentals
- Gulf Shores Vacation rentals
- Orange Beach Vacation rentals
- Miramar Beach Vacation rentals
- Clearwater Vacation rentals
- Santa Rosa Island Vacation rentals
- Beach house rentals Santa Rosa Island
- Rentals with a patio Santa Rosa Island
- Hotel rooms Santa Rosa Island
- Townhouse rentals Santa Rosa Island
- Pet-friendly rentals Santa Rosa Island
- Fitness-friendly rentals Santa Rosa Island
- Rentals with an EV charger Santa Rosa Island
- Rentals with a hot tub Santa Rosa Island
- Beach condo rentals Santa Rosa Island
- Rentals with a kayak Santa Rosa Island
- Rentals with beach access Santa Rosa Island
- Cottage rentals Santa Rosa Island
- Rentals with an accessible height bed Santa Rosa Island
- Family-friendly rentals Santa Rosa Island
- Rentals with an accessible height toilet Santa Rosa Island
- Rentals with a washer and dryer Santa Rosa Island
- Waterfront rentals Santa Rosa Island
- Rentals with a fireplace Santa Rosa Island
- Rentals with outdoor seating Santa Rosa Island
- Apartment rentals Santa Rosa Island
- Beachfront rentals Santa Rosa Island
- Rentals with a sauna Santa Rosa Island
- House rentals Santa Rosa Island
- Villa rentals Santa Rosa Island
- Condo rentals Santa Rosa Island
- Rentals with a fire pit Santa Rosa Island
- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- 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
- Gulfarium Marine Adventure Park
- Pensacola Beach Crosswalk
- Eglin Beach Park
- Raven Golf Club
- Fort Walton Beach Golf Course
- Walton Dunes Beach Access
- Camp Helen State Park
- The Track - Destin
- Fred Gannon Rocky Bayou State Park
- Pensacola Dog Beach West
- Shipwreck Island Waterpark
- Seacrest Beach
- Wayside Park, Okaloosa Island




