
Vacation rentals with a pool in Santa Rosa Island
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Santa Rosa Island

Total vacation rentals
Explore 2,700 vacation rentals in Santa Rosa Island

Nightly prices starting at
Santa Rosa Island vacation rentals start at $125 CAD per night before taxes and fees

Verified guest reviews
Over 57,850 verified reviews to help you choose

Family-friendly vacation rentals
1,990 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

Rentals with dedicated workspaces
1,580 properties have a dedicated workspace

Wifi availability
2,690 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, Gulfarium Marine Adventure Park, and Crab Island
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.

Beach Penthouse on Okaloosa Island in FWB, FL
Unit 301 has the best views being it is an end unit on the top floor. It also feels very spacious with its vaulted ceilings and unique loft area. Sleeps up to 6 people. Queen bed in Master. Another Queen bed and bath in loft. One full size sleeper sofa in living room. Owners have used the unit for past 9 years and have just decided to offer it as a rental. Freshly painted, and updated with new carpets, floors, furniture and appliances. Unit has everything you need for a wonderful vacation.

GULF FRONT TopFloor Amazing VIEW Directly On Beach
Cozy oasis with a view that takes your breath away! You'll enjoy relaxing on the private balcony overlooking the ocean. King bed and twin pullout loveseat. Beautifully renovated kitchen and bath. Fully stocked kitchenette with granite countertops. The full sized refrigerator is a special perk in this Luxury Honeymoon suite. Charming coastal accents throughout. Special attention has been given to this unit to ensure everything is top notch with professional upgrades. Waves roll in, cares roll out

Destin West: Luxurious BAY View BEACH Access CONDO
Enjoy this luxurious 3bd/2ba 1,777 sq ft family friendly condo with a luxury master suite with Jacuzzi; & large balcony overlooking Choctawhatchee Bay. Walk to the dock & eat or sign up for a fishing charter, or rent your own jet skis or pontoon boat and make your way to Destin's Crab Island! Downstairs is the Lazy River, Waterfall pool, 2 heated pools, and 2 heated jet spas. Wristbands are required for this area. Guests can use the sky-bridge to access the beach, restaurants, and entertainment.

Relaxing Gulf Front Couple's Retreat*Beach Service
🌊 Beachfront Bliss on Okaloosa Island – Balcony + Free 2 Chairs & Umbrella Welcome to a perfect escape on Okaloosa Island! Wake up to direct Gulf-front views & private balcony w/ emerald waters & sugar-white sand Beautifully updated studio is designed for a relaxing, stress-free beach getaway—to unwind or work remotely with a view We HIGHLY suggest that you purchase Tavel Insurance as we cannot be responsible for travel interruptions, weather or sickness. We adhere to our cancellation policy.

Luxury Pool/SPA/BEACH, 1BR w/Dol Views, Full KITCN
The Crow’s Nest is part of the Manor on the Bay, a large home transformed into multiple rental units. The full property is also avail for rent. This pvte 2nd story space bosts nautical design elements. Sip coffee on your balcony while watching the dolphins play. With options to cook in the well appointed galley kitchen or check out our local sea food spots, you wont leave here hungry. What I love: ✔ stunning views ✔ pvte space ✔ HUGE luxury spa w/pool & beach ✔ Dolphins! ✔ Book what you need

Condo With Serene Panoramic Views of the Gulf
This newly renovated 2nd floor condominium provides panoramic views in a serene atmosphere directly on the Gulf. This unit features a corner wraparound balcony with master and living room views of the emerald waters gently lapping at the white sand beach. This condo is on the quieter, more secluded end of Okaloosa Island just steps to a private beach. Two reserved beach chairs and service are included in your stay (March-October). Relax with the whole family at this peaceful place to stay.

Oceanfront 3 King BR/3BA Condo Steps 2 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 King 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

Beachfront condo with views
Door to sand in 2-3 minutes. First floor, one flight of stairs and out the private dune walkover, no elevator wait. Gulf view from your balcony, close enough to hear the surf and watch the summer fireworks. Updated unit, pet free building. Private king bedroom, bunk nook off the hall, sleeper sofa. Six sleep, nobody on the floor. Stewby's, ice cream, and putt putt across the street. 15 minutes down the beach to the pier and Boardwalk. 2 chairs and umbrella included, set up for you Mar-Oct.

DestinWest G405 Kid-friendly/oceanview/Lazyriver
[new patio furniture] Destin West Resort Gulfside 405 (2mins to the beach and pool) ~ 1 Bdr + 1 bunkroom with 2 full baths, Sleeps 6 ~ great ocean view ~ free beach service: 2 chairs & 1 umbrella (seasonal: 3/1 - 10/31, 9am-5pm) ~ 1 King Bdr with a private bathroom ~ 1 bunk room (2 twin beds, each with its own TV) with a private bathroom ~ 1 Q pullout sleeper ~ pack n play ~ 4 smart TVs ~ full kitchen stocked with cookware (Keurig and a traditional coffee maker). ~ washer/dryer

Destin West V409 Cozy Beach Getaway 7Amazing Pools
Newly updated modern beach-side unit. Luxurious renovated bathroom. This Gulfside unit is steps away from the white sandy beach, 7 different pools, and many restaurants. Located on the 4th-floor with one of the best views in the Florida panhandle. A 180-degree view of the emerald waters of the Gulf of Mexico, Choctawhatchee Bay, the Okaloosa Island sand dunes, and the Destin city-scape. Relax in the lazy river pool, sunbathe at the beach, or spend your day being adventurous.

Stars & Sea•Overlooking Pool & Sound•Sleeps 4
Kick back & relax in this calm, newly renovated ground-level condo on the Sound in Ft Walton Beach! ✨ Highlights: • 🌴 Waterfront views & stunning sunsets • 💦 Large resort-style pool • 🏖️ Minutes to beach access • 🍽️ Walk to local restaurants • 🚗 Easy parking & quiet community 🛏️ Queen bed w/Purple® mattress + Queen memory-foam sofa bed ☕ Kitchenette: Fridge • Air fryer/toaster • Microwave • Keurig •7.5 Miles to Destin

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

Destin Pointe | Private Pool + Hot Tub | 2 Beaches

B-Fish, Private Pool, Across from Beach, Dogs OK

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

5 Min Walk to Private Beach | Luxury Remodel

#2 4BR HUGE PET Friendly Home Away from Snow!

Waterfront! Sleeps 14 & TWO Story Waterslide Fun!!

Salt Pool & Spa, Heat Opt, Cali King Bed, Beach 4M

Luxurious BeachHouse Pickeball+HeatedPool
Condo rentals with a pool

Waterfront Studio • Santa Rosa Sound • Sunsets

2nd floor beachfront with amazing views

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver

Beachfront Condo | Gulf Views | Okaloosa Island

Ocean Views at Waterscape Resort!

Mermaid Hideaway at El Matador 621!

Luxury 1-bdrm Studio. 2 Pools/Sauna/Hot Tub/Beach

115+ Five-Star Reviews | Renovated Gulf View Condo
Other vacation rentals with a pool

Clean & Luxurious Beachfront ~ 7 Pools+HotTubs+Gym

Pool Table, Lazy River, & HUGE Patio! Destin West!

Its 5 o'clock here

Luxury Beach Front Condo! 3bd/3ba-Waterscape(A301)

"SeaGlass" - Oceanfront with expansive balcony.

605 Destin West Resort - Gulfside Penthouse View!

Gulf Side Villa 503

Vitamin Sea
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 | $226 CAD | $255 CAD | $312 CAD | $315 CAD | $376 CAD | $529 CAD | $425 CAD | $299 CAD | $264 CAD | $256 CAD | $230 CAD | $224 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 |
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- Rentals with pools Okaloosa County
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- Rentals with pools United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pier Park
- Henderson Beach State Park
- Village of Baytowne Wharf
- Seacrest Beach
- Frank Brown Park
- Navarre Beach Fishing Pier
- Aqua Resort
- Johnson's Beach, Gulf Islands National Seashore
- HarborWalk Village
- Topsail Hill Preserve State Park
- Grayton Beach State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Shipwreck Island Waterpark
- The Boardwalk on Okaloosa Island
- Morrison Springs
- Pensacola Bay Center
- Destiny East
- Camp Helen State Park





