
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 ﺩ.ﺇ 331 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 & kid-friendly amenities

Pet-friendly vacation rentals
Find 140 rentals that welcome pets

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

Wi-Fi availability
2,690 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, 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.

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA
Islander Beach Resort is a 7-story structure of 114 condos on a short 2 mile stretch of Okaloosa Island and sits DIRECTLY on the BEACH. The building is painted aqua blue and gray, and all units overlook the ocean. There are 2 elevators and lots of parking. Guests can freely access the beach, HEATED pool, BBQ pits and parking area (a parking pass is needed from lobby). You will probably spend a lot of your time on our large private balcony overlooking the pool and beach, listening to the waves.
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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.
ValueFamilyAccuracy

Beach FRONT Condo-Pools-Lazy River-Free Beach Serv
Hello vacationers! You've found the perfect vacation spot! If you are searching for a beautiful, well-furnished condo with gorgeous 180 degree views of sugar white sand and emerald waters, then you have found the right place. This direct beachfront condo is on Okaloosa Island connecting Destin to Ft. Walton. It's a corner condo with sweeping, unobstructed views. Destin West Resort is in walking distance to so many attractions. FREE beach service included til Oct 31! Must be 25 or older to stay.
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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.
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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, .
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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.
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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!
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Keeler Island Princess #508 Okaloosa Island Bchfrt
Escape the average life at the Majestic Island Princess. Reserve your time today at the Keeler Island Princess #508. Every angle in the living area provides a view so irresistible, you won't be able to take your eyes away from the enticing waters. The diamond sand sparkles with the sun's continuous movement in the sky. Each day, you will discover a new focal point and anticipate its return.
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Okaloosa Island Top Floor 2BR Beach Condo
Welcome to the Islander unit 707, a cozy beachfront condo located on the seventh (top) floor of the Islander Beach Resort on Okaloosa Island. This charming two-beds, two-bathroom unit has everything you need for a comfortable and relaxing stay. Enjoy stunning views of the Gulf of Mexico from the private balcony or take a short stroll to the white sandy beach just steps away.
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Sublime Luxe Retreat + Free Beach Service
Sola Bella | Gulf Dunes 305 A Warm, Light-Filled Beachfront Retreat on Okaloosa Island Welcome to Sola Bella, a bright and inviting gulf-front condo designed for easy coastal living and sun-soaked beach days. With refreshed finishes, comfortable furnishings, and sweeping Gulf views, this thoughtfully updated retreat blends relaxed elegance with everyday comfort.
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2nd floor beachfront with amazing views
Quiet, clean, and recently redecorated, this 2BR condo is right on Fort Walton's unique soft, white, sugar sand. Located in a quiet section of the much-desired Island Echos, this is the perfect place for your relaxing and fun beach vacation! You just can't beat this one for your getaway - we loved it so much we bought it! Guarantee you will love it too!
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Gorgeous Gulf Front condo with amazing views!
Your romantic Gulf-front getaway begins here and is a top-rated destination for couples...This recently updated condo offers new furnishings and is tastefully decorated in warm blue-grey and emerald tones - perfect for a seaside vacation. The Gulf views from your private top floor balcony are unparalleled and promise amazing sunsets.
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Popular amenities for Santa Rosa Island rentals with a pool
House rentals with a pool

Salt Pool & Spa, Heat Opt, Cali King Bed, Beach 4M
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#2 4BR HUGE PET Friendly Home Away from Snow!
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Italian villa 200 steps from beach • Free cruise!
LocationFamilyParking

Emerald Oasis: Hot Tub + Sleeps 18 + Pool+ Grill
ValueFamilySleep quality

Jade East 1250 Corner Condo, Spectacular View~Deal
ValueFamilyBeach

Harbor Central Penthouse
FamilyLocationAccuracy

The Memory Maker - Heated Pool! 4BR Vacation Home
LocationFamilyParks

Relaxing Pool Retreat Near Beaches & Destin!
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Condo rentals with a pool

Veranda 102 - Direct Beachfront - Gulf Side Pool
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Relaxing Gulf Front Couple's Retreat*Beach Service
ValueLocationTV

Direct Gulf Views, Private Pool, Sleeps 4
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Direct Beach FRONT-Amazing Views-Lazy River-Pools!
ValueLocationKitchen

Beachfront Bliss! Gulf Waves at The Palms #201
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Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf
ValueFamilyAccess

GULF FRONT TopFloor Amazing VIEW Directly On Beach
ValueLocationKitchen

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

Blu 100, 2019 Build, Ground Floor, 2 parking spots
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Little Blue Gem
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"SeaGlass" - Oceanfront with expansive balcony.
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Sunset Dreamin! Gorgeous 2BR Panoramic Water Views
LocationFamilyAccuracy

Newly Remodeled Beachfront w/ Amazing View Destin
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Gulf-Front Escape on Okaloosa Island (Veranda 203)
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Beach Side 1/1 Condo Paradise
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* Incredible views ! Dropped rates !
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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 | ﺩ.ﺇ 595 | ﺩ.ﺇ 672 | ﺩ.ﺇ 823 | ﺩ.ﺇ 830 | ﺩ.ﺇ 992 | ﺩ.ﺇ 1,396 | ﺩ.ﺇ 1,120 | ﺩ.ﺇ 790 | ﺩ.ﺇ 698 | ﺩ.ﺇ 676 | ﺩ.ﺇ 606 | ﺩ.ﺇ 591 |
| 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
- Frank Brown Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- Aqua Resort
- HarborWalk Village
- Grayton Beach State Park
- Topsail Hill Preserve State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Shipwreck Island Waterpark
- Morrison Springs
- Camp Helen State Park
- Pensacola Bay Center
- Gulf World Marine Park
- Johnson Beach





