
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.
LocationValueComfort

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.
LocationValueWifi

Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!
Walk to the Beach at Sunset or Sunrise Every Day! 2 pools, indoor pool & outdoor pool next to the White Sand Beach Access, BBQ Area, elevator & fitness room amenity. Come and enjoy Fun & Sun at our condo by the beach! Gorgeous 2 Br 2 Ba condo is an amazingly nice & quiet like open air community on 2nd floor/elevator, balcony view looks over the neighboring county beach access and down the shoreline PERFECT for those summer fun & sunsets! Morning /Afternoon Walk on the 2 miles Santa Rosa Blvd.
FamilyLocationBathroom

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.
ValueLocationHospitality

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.
FamilyLocationWalkability

Penthouse-Huge Roof Top Patio w/ Hot Tub-LazyRiver
Our spacious Penthouse has amazing views on top of the world! Come enjoy our lovely condo with a roof top patio & private hot tub to see all of Okaloosa Island beach & bay for miles. Or have a romantic evening on the roof top patio with a huge hot tub that overlooks beautiful Choctawhatchee Bay. Located on Okaloosa Island at Destin West Beach and Bay Resort, this island connects Destin to Fort Walton Beach. We are on the bayside. We now offer 1 FREE set-up of beach service March 1-Oct.31st.
LocationValueOutdoor spaces

Cheery Condo-Free Beach Service-Direct Ocean View!
Let your cares literally drift away in this relaxing, kid-friendly, beautifully decorated condo with a King bed w/bath + twin/twin bunk area w/bath - Queen LR sleeper sofa. Enjoy stunning views of the Gulf of Mexico and pool area from your private balcony. We invite you to enjoy your special vacation at this perfect Emerald Coast paradise. Free beach service (2 chairs and umbrella) is INCLUDED! (March 1-Oct 31). *Note - Okaloosa County Tourist Tax of 6% will be applied to this booking.
LocationValueNearby

Ocean view condo, Lazy River & Beach, Destin West
From your unit on the Gulf side of the resort, enjoy the spectacular ocean view, award winning lazy river, and many pools in this family friendly Destin West Beach and Bay Resort with private beach. Your unit is a couple blocks from Gulfarium Marine Adventure park, where you can swimming with dolphins. Enjoy the Broadwalk Okaloosa Island with seaside shops, eats, and entertainment within a block. Okaloosa Island fishing pier is within 2 blocks for fishing enthusiasts.
LocationFamilyIndoor spaces

Okaloosa Island Gulf View Resort Studio w/ Balcony
Escape to the stunning white sand beaches of the Gulf of Mexico and stay in this charming studio condo on Okaloosa Island! Located in the popular Islander Beach Resort, this unit is newly renovated and boasts breathtaking views of the emerald green waters. Step outside onto your private balcony to watch the sunset or enjoy your morning coffee with the sound of the waves. Book your stay today and experience the best of the Florida panhandle!
ValueLocationComfort

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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Direct Gulf Views, Private Pool, Sleeps 4
Wake up to the sound of waves and step onto your private balcony to watch the sun rise and set over the Gulf of Mexico. This beautifully appointed 1-bedroom condo sleeps 4 in a charming 9-unit boutique building — meaning no crowded elevators, no packed pool, and your own quiet slice of the Emerald Coast. Looking for a warm winter escape? Monthly rates and snowbird discounts available November through March.
FamilyLocationSleep quality

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.
ValueLocationIndoor spaces
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
FamilyLocationNearby

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

Touch of Madagascar-Whole House
ValueFamilyNearby

Italian villa 200 steps from beach • Free cruise!
ValueFamilyTV

Destin Miramar Walk To Beach Pet Friendly
LocationValueCheckout

Relaxing Pool Retreat Near Beaches & Destin!
LocationFamilyNearby

Destin Pointe | Private Pool + Hot Tub | 2 Beaches
FamilyLocationBeach

5 Min Walk to Private Beach | Luxury Remodel
LocationFamilyPool
Condo rentals with a pool

Destin West V409 Cozy Beach Getaway 7Amazing Pools
LocationFamilySleep quality

216 | Free Beach Svc + Beach Towels +Luxe Interior
LocationFamilyNearby

Beachfront Condo | Gulf Views | Okaloosa Island
FamilyValueDecor

Beachfront Bliss! Gulf Waves at The Palms #201
FamilyValueWalkability

DestinWest G405 Kid-friendly/oceanview/Lazyriver
ValueFamilyHospitality

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

Gorgeous Gulf Front condo with amazing views!
LocationValueCleanliness

Sunshine and beach time /Okaloosa Island
ValueFamilyKitchen
Other vacation rentals with a pool

1203 Oceanfront Pelican Beach: Pools/HTubs Fab Loc
ValueLocationAccuracy

Unobstructed Gulf Views · Sleeps 8
ValueLocationBathroom

Little Blue Gem
LocationFamilyAccuracy

Sunset Dreamin! Gorgeous 2BR Panoramic Water Views
FamilyValueParking

Newly Remodeled Beachfront w/ Amazing View Destin
FamilyLocationBeach

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

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

Gulf-Front Escape on Okaloosa Island (Veranda 203)
ValueLocationParking
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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- 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
- Gulf Breeze Zoo
- Topsail Hill Preserve State Park
- Fort Walton Beach Landing
- Jade East Towers
- Morrison Springs
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulf World Marine Park
- Pensacola Bay Center
- Johnson Beach





