Vacation rentals with beach access in Oldsmar

4.97 out of 5 average rating, 135 reviews

Condo in Clearwater

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

🌴 😎 Stunning Key West Style Retreat featuring: - Memory foam Queen bed - Covered porch for unwinding - Hotel linens, towels and many creature comforts Enjoy the beach 🏄‍♂️ vibes decor & accents in this spacious two bed two bath property. Located less than three miles from the white, sugar sand of Clearwater Beach 😎 (rated #1 beach in the US by Trip Advisor). Relax by the oversized resort style pool and clubhouse. Convenient walking distance to nearby restaurants and grocery stores.

4.88 out of 5 average rating, 108 reviews

A well-maintained pool area features two inviting swimming pools, surrounded by lounge chairs. A hot tub is positioned nearby, with palm trees visible in the background. Outdoor lighting enhances the space, creating a relaxing atmosphere for guests to enjoy.

Condo in Dunedin

Condo w/ Pool, Hot Tub and Restaurant! Book now !

Plan your unforgettable stay at this 1 bedroom condo at Beso ( not a studio) with 2 Balconies for your morning coffee or beautiful sunsets The location is perfect to walk to town where you’ll find many Quaint shops, restaurants and Breweries Free Wi-fi Free parking Only 10 min to honeymoon island and the ferry to Caladesi Island 15 minutes to Clearwater Beach 2 salt water Pools and a hot tub Marker 8 Tiki Bar and restaurant 28 mile trail across St. Bicycle rental through the office for a fee

4.89 out of 5 average rating, 272 reviews

A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.

Home in Tampa Heights

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

4.98 out of 5 average rating, 161 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.96 out of 5 average rating, 160 reviews

A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

4.9 out of 5 average rating, 163 reviews

Condo in Indian Shores

Gulf Side Florida Charm 1/1 Condo 60 Steps To Sand

Step back in time at Postcard Paradise, a charming beachside cottage that captures the magic of Old Florida. Nestled just steps from the shore, our eclectic retreat feels like living inside a vintage postcard. Sun-faded colors, and tropical murals set a nostalgic mood, while modern comforts keep things easy and relaxed. Each cozy room is filled with hand-picked decorations, breezy linens, and quirky coastal finds, creating a one-of-a-kind space where every corner tells a story.

5 out of 5 average rating, 102 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guesthouse in Ozona

Private pool, steps to gulf, fishing, bike trails

Escape to your private Palm Harbor oasis! This updated studio features a cozy queen bed, sofa bed, and kitchenette, plus a sparkling in-ground pool reserved just for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or hop on the nearby Pinellas Trail for biking and exploring. Enjoy beaches just minutes away, along with amazing dining, breweries, and live music in historic downtown. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

4.99 out of 5 average rating, 263 reviews

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

Apartment in Dunedin

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Apartment in Clearwater Beach

A well-lit living area features a cozy couch facing a television. A small dining table and chairs are present nearby, and a ceiling fan hangs above. Large windows allow natural light to fill the room, complementing light-colored walls and wood-look flooring.

4.89 out of 5 average rating, 149 reviews

Coastal Waterside Condo 2 Blocks to Beach

🌊 Ultimate Waterfront Escape – Adventure Awaits! 🚴‍♂️🏄‍♂️ Welcome to your dream beach getaway! This stunning waterfront rental puts you right on the water with breathtaking views and endless adventure. Paddle on a kayak or stand-up paddleboard, then cruise around town on our complimentary beach bikes. Jet ski island tours, parasailing, and more. We are pet friendly! Pet fee is $150 for the first dog, $100 for the second dog.

4.84 out of 5 average rating, 261 reviews

A cozy sleeping area is presented with a spacious bed covered in a decorative quilt. A piece of wall art adds character, while natural light filters in through a small window. A mirror panel reflects the room's tranquil atmosphere.

Guesthouse in Tampa

Cozy Suite

Hermosa suite acogedora en la bahía de Tampa, con patio amplio y lindo jardín para disfrutar de momentos agradables e íntimos al aire Libre. Habitación acogedora y totalmente equipada para su disfrute. Baño con ducha dentro de la habitación. Cuenta con cocina totalmente equipada y refrigerador. También dispone de comedor y un espacio con escritorio y silla para trabajar. Dispone de Wifi en toda la habitación

4.96 out of 5 average rating, 200 reviews

A compact kitchen area includes a white refrigerator, an oven, and a microwave, all arranged neatly against light cabinetry. A circular clock in red and black adorns the wall, while a small black dining table with two chairs is positioned in front. Glassware and kitchen accessories are displayed on open shelving.

Apartment in Dunedin

Cozy Apartment Overlooking Downtown Dunedin

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. Second floor 1 bedroom apartment is totally renovated. Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more. Sit on the front porch and see all Dunedin has to offer.

4.87 out of 5 average rating, 141 reviews

The bedroom features a spacious bed with soothing neutral bedding, paired with accent pillows. A stylish desk sits beside the bed, enhanced by natural light from a nearby window. A ceiling fan and mounted TV add convenience, while decorative wall art complements the modern design.

Home in Tarpon Springs

MODERN/Mins to Beach/walk to dwtn/Free parking

🌴 Escape to Tarpon Springs! This newly renovated 1B/1B private home is perfectly located—just 5 minutes to the beach and the famous Sponge Docks, and a short stroll to charming downtown. Whether you’re here to relax, explore, or soak in the local culture, this getaway puts you right in the heart of it all.

Popular amenities for Oldsmar beach access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

Apartment in Madeira Beach

A direct view of the Gulf shoreline is visible from the balcony, showcasing a sandy beach with beach chairs and umbrellas. A private pool is located below, surrounded by a patio area with several lounge chairs, creating an inviting setting for relaxation.

4.9 out of 5 average rating, 102 reviews

Welcome to Gulf-Front Paradise!

Apartment in Historic Kenwood

A charming two-story bungalow surrounded by lush greenery and outdoor seating. The entrance features a set of steps leading to a wooden porch, framed by large windows that invite natural light. The yard includes various plants, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 398 reviews

Historic Kenwood Getaway

Apartment in Clearwater Beach

An open living area features a blue couch and two bar stools at a kitchen counter. A green bed is visible in the background, with a light-colored dresser against the wall. Soft lighting brightens the space, which has light blue walls and patterned flooring.

4.94 out of 5 average rating, 144 reviews

NEW! High End King Mattress! 10 Steps to the beach

Apartment in Indian Shores

A spacious living area is furnished with two comfortable leather sofas and a wooden side table. A large flat-screen TV is positioned nearby. Natural light floods the room through expansive glass doors leading to a balcony, with ocean views visible in the distance.

4.92 out of 5 average rating, 191 reviews

Beach Front Condo!

Apartment in Independence Square

A view from the balcony captures a stunning sunset over the Gulf, where vibrant hues blend in the sky. The sandy beach is visible below, with a winding path leading to the shoreline. Figures can be seen strolling along the beach, adding life to the serene scene.

4.96 out of 5 average rating, 180 reviews

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Apartment in Pinellas Park

The living area features a wall-mounted television, a glass coffee table, and a comfortable sofa. A dining table with two chairs and an extra chair are positioned near a window. Soft lighting is provided by a pendant light and ceiling fan.

4.86 out of 5 average rating, 188 reviews

Cozy little getaway

Apartment in Indian Rocks Beach

A sandy pathway leads from a wooden deck to the beach, framed by wooden railings. The expansive shoreline is visible, with gentle waves lapping at the shore under a bright blue sky. Beachgoers can be seen enjoying the sun and water in the distance.

4.78 out of 5 average rating, 100 reviews

20 Steps To The Beach | Private 1BR Unit On Beach

4.94 out of 5 average rating, 116 reviews

A cozy sleeping area features a spacious bed covered with a soft turquoise quilt and decorative pillows. In the background, a small dining table with two chairs is visible, along with a kitchenette equipped with essential appliances and storage.

Apartment in Tampa

Cuddle Sack near RayStadium, TPA, Busch Gar, beach

House rentals with beach access

4.99 out of 5 average rating, 196 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

4.86 out of 5 average rating, 240 reviews

A covered patio area is furnished with two blue chairs and a small round table. The space is enclosed by a wooden fence and features a grassy area along with gravel, creating a relaxed outdoor setting.

Home in Tampa

Boho Villa

4.79 out of 5 average rating, 136 reviews

A covered swimming pool area features a clear and inviting pool, surrounded by a spacious patio with tiled flooring. Large glass doors allow natural light to flood the space, while lounge chairs are positioned nearby, offering a comfortable spot to relax.

Home in Dunedin

The House of Relaxation

4.98 out of 5 average rating, 205 reviews

Home in St. Petersburg

Sparkling Modern Pool Home with Guest Bungalow!

4.93 out of 5 average rating, 122 reviews

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

4.83 out of 5 average rating, 115 reviews

The spacious living room is adorned with a large blue sectional sofa and a stylish yellow accent chair. A round coffee table sits on a decorative rug, while a smart TV is positioned on an entertainment center. Natural light enters through the blinds of the windows, illuminating the room.

Home in Tampa

🗝Home in Tampa Bay for a cozy stay☀️

4.74 out of 5 average rating, 120 reviews

Home in Tampa

Walk to Raymond James Stadium! Pool/ Hot Tub Home!

4.91 out of 5 average rating, 97 reviews

A stylish kitchen area is highlighted by mid-century modern furniture and wooden accents. A spacious island with seating for three is present, complemented by white cabinetry. Exposed beams create an open feel, while natural light enters through the window, enhancing the brightness of the space.

Home in Dunedin

Serenity Bungalow Downtown

Condo rentals with beach access

Condo in Indian Rocks Beach

The inviting living space is furnished with a blue sofa, two armchairs, and a white coffee table. A starfish-patterned rug adds a nautical touch. Natural light filters through window blinds, illuminating the area. The open layout connects to the kitchen, visible in the background.

4.97 out of 5 average rating, 128 reviews

Renovated Condo! Across the Street From The Beach

4.98 out of 5 average rating, 101 reviews

Condo in Clearwater

Lovely Condo minutes from beach & King bed

4.75 out of 5 average rating, 259 reviews

A wooden pier extends over smooth waters, bordered by rocky outcrops. The sky is painted in vibrant hues of orange and purple as the sun sets on the horizon, casting a tranquil glow across the scene.

Condo in Tampa

Rocky Point paradise

4.8 out of 5 average rating, 213 reviews

A bright living area features large windows that allow natural light to filter in, creating an airy ambiance. A comfortable seating arrangement is complemented by a dining table set with round placemats. A ceiling fan adds a cooling feature, and beach-themed artwork decorates the walls.

Condo in Madeira Beach

Coastal Retreat Madeira Beach/John’s Pass Pool

4.94 out of 5 average rating, 133 reviews

The image captures a view from the condo balcony, showing a clear blue sky and the tranquil Gulf of Mexico. The pool area is visible, featuring a large swimming pool surrounded by lounge chairs. Beach umbrellas dot the sandy shore, providing a vibrant contrast.

Condo in Indian Shores

Tropical Beachfront Penthouse-Beach Cottages

4.85 out of 5 average rating, 112 reviews

Condo in Tampa

Waterfront Condo with Heated Swimming Pool

4.99 out of 5 average rating, 209 reviews

An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.

Condo in Treasure Island

Spectacular beach to bay views from this resort.