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Vacation rentals with a pool in Bay Pines

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Bay Pines

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Condo in Redington Beach

4.89 out of 5 average rating, 159 reviews

SWEET BEACH RETREAT - REDINGTON BEACH FLORIDA

Great beach living with lush views, a heated pool & a low-key atmosphere. Access to the Gulf of Mexico across the street. This CLEAN studio has a full kitchen, a queen bed, WiFi & TV, plus a sleeper sofa. This is great HOLIDAY living. Dine outdoors on the balcony overlooking the courtyard. EnJOY the recreation park next door, with views, a workout station, and a picnic area. Parking is onsite. Close to St. Pete, Clearwater, & St. John's. Owner has put this condo on the market & it is for sale.

Guesthouse in St. Petersburg

4.9 out of 5 average rating, 484 reviews

Private Guest House sleeps 4 w/POOL & near beach!

This adorable pool house is light and airy with plenty of room for 4. There’s a king size bed, queen pullout sofa, dining area, efficiency kitchen perfect for light cooking, oversized closet and a newly remodeled bathroom. Guests have private entrance with small yard and patio of their own, and are encouraged to use the pool and backyard anytime, which we enjoy along with our sweet dogs, Frog and Bella. 3 miles from beach and downtown, lots of restaurants and shopping centers within 1.5 miles.

Home in Saint Petersburg

4.89 out of 5 average rating, 342 reviews

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Vibrant 2BR/1Bath home sleeps 8 guests and has a magical outdoor space designed to create beautiful memories! A tropical saltwater pool and large covered entertainment area complete with a TV—perfect for relaxing and enjoying a cocktail. The interior is colorfully curated to embody the essence of a vacation! Located just 5 minutes from the beach and 25 minutes to downtown. We have 16 Airbnb homes (family-owned and operated), and we're dedicated to finding the perfect fit for your getaway.

Home in St. Petersburg

4.97 out of 5 average rating, 128 reviews

The Blue Fin, comfortable 3 bed, heated pool house

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you swim and enjoy the salt water heated pool. Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

Home in St. Petersburg

5 out of 5 average rating, 138 reviews

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

Guesthouse in St. Petersburg

4.98 out of 5 average rating, 159 reviews

Central Cozy Cottage w/ Heated Pool & Hot Tub!

Welcome to cute & cozy Turtle Cottage located right in the center of St. Pete, close to both Downtown AND several gorgeous Florida beaches. NO CLEANING FEE with competitive, seasonal pricing = a FANTASTIC DEAL for this space! A BEAUTIFUL NEW HEATED POOL & HOT TUB await in the private, fenced-in tropical backyard. Sorry, no pets/animals or babies/children/teens. Adults 21+ only and limited to 2 verified guests. 100% smoke-free property, inside & out. DEI honored here. Come & enjoy!

Condo in Seminole

4.97 out of 5 average rating, 203 reviews

UPDATEDVacation condo! HEATEDpool3 miles to beach

No damage from Helene or Milton! Wow!! Super value !! 2 bed 1 bath condo - Welcome to Beachway Condos a GATED SAFE private full amenity community featuring a gym, tennis courts, HEATED POOL, grills, located 3 miles to the beautiful gulf beaches. You are close to everything - the Pinellas trail biking/walking is 1/4 mile away, Indian shores beach is the closest beach at 3 miles away. Clearwater/st Pete beaches are 7 miles away. Across the street are grocery stores malls, restaurants

Rental unit in Saint Petersburg

4.89 out of 5 average rating, 157 reviews

The Oasis

Welcome to Boca Ciega Oasis! The "Oasis" suite 409 has been totally remodeled in January 2022. This includes a new queen sofa couch in LR, new refrigerator, stove, washer/dryer, and balcony tables and chairs. The 4th-floor view is the best but 409 is also centered beautifully to take in the expansive Boca Ciega Bay! Directly below the balcony is the swimming pool, Hot tub, and observation pier! The marina is to your left. See all while sitting in our bar height chairs and tables.

Condo in St. Petersburg

4.95 out of 5 average rating, 230 reviews

Waterfront condo! Mins to beach! Great location!

This unit was completely updated and quite modern! Two TV's in the unit, plus a GORGEOUS view from the 20' private balcony overlooking the Bay! This condo in St. Petersburg is in a great location close to all amenities with many restaurants nearby, including Doc Ford's next door, and shopping nearby. Lots to do; and a 6 minute drive to Madeira Beach! Close to fishing including deep sea. 1-bedroom, condo sleeps 2 (plus up to 2 small children on the pull-out couch).

Condo in St. Petersburg

4.8 out of 5 average rating, 181 reviews

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

Condo in Redington Beach

4.88 out of 5 average rating, 130 reviews

Royal Orleans and Redington Beach ( Studio 203 )

Royal Orleans 203 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

Guest suite in Seminole

4.92 out of 5 average rating, 138 reviews

Comfy Pool Suite, Private Entry, King Bd, Beach 1m

Complete privacy and quiet on your closed-off side of the house. One mile to Reddington and Indian Shore Beaches. 10 minute drive to Madeira or Clearwater Beach. Also minutes away from a wide variety of restaurants and shopping. Driveway parking by your private entrance for convenient loading. No stairs, just a 1-step threshold. Comfy king-sized bed. Beach chairs, beach towels, umbrellas available for guest use.

Vacation rentals for every style

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Apartments

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Popular amenities for Bay Pines rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Largo

4.86 out of 5 average rating, 109 reviews

The Paradise Cove No. 2

Home in Largo

4.96 out of 5 average rating, 152 reviews

Palm House~Heated Pool~8 min to Beach

Home in Pinellas Park

4.98 out of 5 average rating, 101 reviews

Insta Worthy Retreat - Heated pool-putt putt | Bar

Home in Seminole

4.95 out of 5 average rating, 274 reviews

Ready to go! Heated Pool/Hot Tub Luxury Home

Home in Seminole

4.88 out of 5 average rating, 152 reviews

*POOL* Bar, Hottub, Central location

Home in St. Petersburg

4.87 out of 5 average rating, 77 reviews

3BR St. Pete Home, Heated Pool, 5 Min To Beaches

Home in Pinellas Park

4.87 out of 5 average rating, 110 reviews

Anchors Away! Charming 3 bedroom with heated pool

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

Condo rentals with a pool

Condo in Redington Beach

4.93 out of 5 average rating, 369 reviews

Beach Condo, Heated Pool, 2 Minute Walk to Ocean

Condo in Redington Beach

4.85 out of 5 average rating, 600 reviews

Condo II:Beach 2 min walk:Heated Pool:Grill

Condo in Redington Beach

4.8 out of 5 average rating, 199 reviews

Gulf view Condo with pool in Clearwater/St. Pete

Condo in Redington Shores

4.82 out of 5 average rating, 153 reviews

Beach Studio 5

Condo in Sunset Beach

4.89 out of 5 average rating, 240 reviews

Sunset Beach Condo in Treasure Island

Condo in Redington Beach

4.8 out of 5 average rating, 219 reviews

Beautiful Studio on the paradise white sand beach!

Condo in Indian Shores

4.94 out of 5 average rating, 155 reviews

1 BR Beachfront Amazing sunsets-

Condo in Treasure Island

4.98 out of 5 average rating, 105 reviews

Beach, sunsets, manatee sightings, fishing & rest!

Quick stats about vacation rentals with a pool in Bay Pines

Total rentals
120 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
70 properties have a dedicated workspace

Destinations to explore