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

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

Nightly prices starting at
Santa Rosa Island holiday rentals start at $157 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
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 holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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

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.

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.

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 Villa #V502 Beach Vacation Awaits
7POOLS🏊♀️LAZY RIVER 🏖️ PRIVATE BEACH YOUR PERFECT MODERN COASTAL RETREAT IS WAITING! 🌴☀️ Whether you’re planning a romantic escape , a fun-filled family getaway , or a memorable trip with friends, this modern coastal retreat offers the perfect blend of relaxation, recreation, and unforgettable seaside moments. Enjoy so many resort-style amenities, you may never want to leave. And when adventure calls, you’ll be right in the center of it all.

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!

Beachfront Bliss! Gulf Waves at The Palms #201
Wake up to gorgeous Gulf views at The Palms #201! 🌊 This beachfront 2BR/2BA end unit sleeps 6 with 2 king beds and a sofa sleeper. Enjoy water views from the living room, kitchen, and primary bedroom—then take the elevator down and step onto the sand. You’ll also get a reserved garage parking space and free daily beach service from March through October, including 2 chairs and an umbrella—a $40/day value! ☀️

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.

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.

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.

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

Sugar Sand Cottage at Destin Pointe

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

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

Harbor Central Penthouse

Touch of Madagascar-Whole House

5 Min Walk to Private Beach | Luxury Remodel

Relaxing Pool Retreat Near Beaches & Destin!

Italian villa 200 steps from beach • Free cruise!
Condo rentals with a pool

ISLANDER BEACH 5TH FLOOR GULF VIEW CONDO - 2BD/2BA

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

Beachfront Condo | Gulf Views | Okaloosa Island

Beachfront Bliss 2BR/2BA Condo Stunning Ocean View

Beach Side- 2Br 2Ba 3bed | POOLS- GEM-BEACH!

Sunshine and beach time /Okaloosa Island

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

Stars & Sea•Overlooking Pool & Sound•Sleeps 4
Other holiday rentals with a pool

Okaloosa Island Beach Condo14/Small Pet/Pool/Grill

Oceanfront 3 King BR/3BA Condo Steps 2 Sand & Surf

Sunset Dreamin! Gorgeous 2BR Panoramic Water Views

Gulf-Front Escape on Okaloosa Island (Veranda 203)

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

Newly Remodeled Beachfront w/ Amazing View Destin

3BR ~ Beachfront ~ Huge Balcony ~ 2 Pools ~ Luxury

A-Fish, Private Pool, Across from Beach, Dogs OK
When is the best time to visit Santa Rosa Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $282 NZD | $318 NZD | $390 NZD | $393 NZD | $470 NZD | $661 NZD | $530 NZD | $374 NZD | $330 NZD | $320 NZD | $287 NZD | $280 NZD |
| 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 |
Destinations to explore
- Atlanta Holiday rentals
- New Orleans Holiday rentals
- Panama City Beach Holiday rentals
- Destin Holiday rentals
- Gulf Shores Holiday rentals
- Jacksonville Holiday rentals
- Miramar Beach Holiday rentals
- Orange Beach Holiday rentals
- Birmingham Holiday rentals
- Clearwater Holiday rentals
- Pensacola Holiday rentals
- Tallahassee Holiday rentals
- Family-friendly rentals Santa Rosa Island
- Apartment rentals Santa Rosa Island
- Beachfront rentals Santa Rosa Island
- Rentals with breakfast Santa Rosa Island
- Condo rentals Santa Rosa Island
- Rentals with beach access Santa Rosa Island
- Rentals with lake access Santa Rosa Island
- Beach house rentals Santa Rosa Island
- Rentals with an accessible height bed Santa Rosa Island
- Pet-friendly rentals Santa Rosa Island
- Resort rentals Santa Rosa Island
- Hotel rooms Santa Rosa Island
- Rentals with a kayak Santa Rosa Island
- Waterfront rentals Santa Rosa Island
- Cottage rentals Santa Rosa Island
- Beach condo rentals Santa Rosa Island
- Rentals with an accessible height toilet Santa Rosa Island
- Villa rentals Santa Rosa Island
- House rentals Santa Rosa Island
- Rentals with a hot tub Santa Rosa Island
- Townhouse rentals Santa Rosa Island
- Rentals with a sauna Santa Rosa Island
- Rentals with pools Okaloosa County
- Rentals with pools Florida
- Rentals with pools United States
- Destin Beach
- Crab Island
- Destin Harbor Boardwalk
- Opal Beach
- Pier Park
- Village of Baytowne Wharf
- Henderson Beach State Park
- Frank Brown Park
- Seacrest Beach
- Navarre Beach Fishing Pier
- Johnson's Beach, Gulf Islands National Seashore
- HarborWalk Village
- Aqua Resort
- Grayton Beach State Park
- Topsail Hill Preserve State Park
- Gulf Breeze Zoo
- Fort Walton Beach Landing
- Jade East Towers
- Morrison Springs
- Shipwreck Island Waterpark
- Camp Helen State Park
- Gulf World Marine Park
- Gulfarium Marine Adventure Park
- Pensacola Bay Center





