Holiday rentals with beach access in Oldsmar

4.97 out of 5 average rating, 131 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.

4.9 out of 5 average rating, 248 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).

4.96 out of 5 average rating, 140 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.

Guesthouse in Tarpon Springs

A comfortable living space includes a dark blue sofa with accent pillows and a coffee table. A dining area with wooden chairs is visible in the background, alongside a fully equipped kitchen. Light-colored cabinets and appliances complement the space.

4.85 out of 5 average rating, 101 reviews

Comfy 1BR Near Beaches & Sponge Docks

Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

4.99 out of 5 average rating, 141 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, 334 reviews

A well-lit bedroom features a spacious bed layered with a white comforter. A light-colored dresser is positioned against the wall opposite, along with a flat-screen TV. Natural light filters through a large window, adorned with sheer curtains that gently frame the view outside.

Home in Tampa

Cottage in the heart of Tampa close to everything

Centrally located, safe & desirable neighborhood by Hillsborough River. Corner lot, Free covered parking, easy self checkin, Bohemian style decor & vibe, stocked kitchen, SMART TVs, Laundry Rm, Fireplace. Outside Fire Pit, Picnic Table w/BBQ Grill, Hammock. Close to Lowry Park Zoo, Downtown/Convention Center, Riverwalk, Armature Works, Ybor City, Busch Gardens, Hyde Pk, Midtown, Airport, Beaches & More. Perfect for Vacation, Romantic Getaways, Family Visits, Concerts, Hockey/Football, & Work.

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 134 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

Tiny home in Tarpon Springs

A serene sleeping area features a large bed adorned with multi-colored striped blankets and a cozy yellow throw. Natural light fills the space through two windows, illuminating the wooden accents and white walls.

4.88 out of 5 average rating, 273 reviews

Driftwood Surf Shack

This unique Surf Shack is a guest home that sleeps up 4 & still plenty of room to relax inside or outside on the large wood deck situated under a beautiful oak tree. Located in the historic district Tarpon, just blocks from Downtown, the famous Sponge Docks & Craig Park where you can watch dolphins feed at sunset in the many Bayous. Close to beaches, shopping, restaurants, breweries, boat excursions, water sports & the Pinellas Trails you will never get bored in this town!

4.99 out of 5 average rating, 255 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

4.88 out of 5 average rating, 172 reviews

A modern kitchen area features sleek white cabinetry, gray countertops, and stainless steel appliances. An island with two black stools offers additional seating. Well-lit by overhead fixtures, the space includes a door leading to an entrance and a doorway to a small adjacent room.

Villa in Tampa

Boho -Minimalist villa

Welcome to our Boho Minimalist Villa 4311 unit B with a 2 bedroom and 1 bathroom. Conveniently located in the heart of Tampa, Florida. “Points of interest” to visit and enjoy while you are here: Raymond’s James Stadium, New York Yankees Training Camp, Hillsborough Community College, International Tampa Airport, Downtown Tampa, Midtown within less than 10-minutes’ drive enjoy a great afternoon eating at many local restaurants.

4.83 out of 5 average rating, 257 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, 195 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.

Popular amenities for Oldsmar Accommodation with Beach Access

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Apartment rentals with beach access

4.77 out of 5 average rating, 108 reviews

Apartment in Tampa

Heated Pool, Amazing Waterfront Views Reduced 20%!

4.95 out of 5 average rating, 100 reviews

A serene outdoor space features a winding pathway of stone slabs leading to a decorative garden statue surrounded by lush palm trees. The natural landscaping provides privacy and a peaceful atmosphere within the courtyard.

Apartment in Largo

Hidden Oasis #3, just a few mins to the beach

4.82 out of 5 average rating, 117 reviews

A bright living area features a comfortable gray sofa and a wooden coffee table atop a patterned rug. The open kitchen, visible in the background, is equipped with modern appliances and sleek cabinetry. A fan hangs from the ceiling, complementing the airy feel of the space.

Apartment in Clearwater

Coastal Waterview Condo 10 min to Beach

4.97 out of 5 average rating, 382 reviews

A modern bathroom featuring a round mirror above an elegant wooden sink with a metallic bowl. Exposed brick walls and dark accents create an industrial feel. A sleek, black toilet complements the stylish glass shower, which is designed with contemporary tile.

Apartment in Tampa

Hyde Park "Industrial-chic" with Private Backyard

Apartment in Pinellas Park

A charming terrace features a jacuzzi surrounded by wooden walls adorned with greenery. Soft lighting illuminates the space, creating a cozy atmosphere. Two turquoise chairs and a small blue table invite relaxation and conversation.

4.81 out of 5 average rating, 187 reviews

“Oasis Terrace”

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.

4.88 out of 5 average rating, 182 reviews

Cozy little getaway

Apartment in Indian Rocks Beach

An aerial view captures the serene coastline and vibrant community of Indian Rocks Beach. The expanse of blue water meets the sandy shore, with buildings and residences lined along the beach. Green parks and water channels are visible, enhancing the coastal atmosphere.

4.96 out of 5 average rating, 113 reviews

Cozy coastal grandmother condo, walk to the beach!

4.94 out of 5 average rating, 114 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

Cozy studio near RayStadium, TPA, Busch Gar, beach

Holiday House Rentals with beach access

4.91 out of 5 average rating, 109 reviews

An inviting pool area features a clear blue pool alongside a spacious hot tub, both surrounded by a grey stone deck. Comfortable loungers are arranged under an umbrella, offering shade. Sunlight filters through the screened enclosure, creating a bright and open atmosphere.

Home in Largo

Heated Pool and Spa | 5 min to beach

4.93 out of 5 average rating, 130 reviews

A spacious living area features a large sectional sofa adorned with various decorative pillows. A light-colored coffee table is positioned in the center, complemented by a decorative basket. Natural light filters through two window blinds, creating a bright and inviting environment.

Home in Dunedin

Ocean Sunsets & Downtown Biking Trails

4.96 out of 5 average rating, 126 reviews

The exterior of the home features a sandy-colored facade with a bright blue front door. Lush greenery surrounds the property, including trees and shrubs. The fenced yard offers a sense of privacy, and a clear blue sky serves as the backdrop.

Home in Seminole

Beach 5-Min (Near Tampa & Clearwater)

5 out of 5 average rating, 185 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

4.79 out of 5 average rating, 135 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

House of Relaxation

4.81 out of 5 average rating, 108 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☀️

4.86 out of 5 average rating, 111 reviews

A private pool is surrounded by a spacious concrete deck, featuring several lounge chairs and tropical landscaping. The clear blue water is set against a backdrop of a blue sky and a white fence, creating an inviting outdoor retreat.

Home in Tampa

Luxurious House with private Pool.

4.86 out of 5 average rating, 109 reviews

A serene view of the waterfront home, featuring a clear blue pool and well-maintained lawn. Two bright green jet skis are docked at the wooden pier, which extends into the calm canal. The house's backyard is framed by palm trees, creating a relaxed outdoor environment.

Home in Dana Shores

Boaters Paradise- Waterfront Heated Pool King Beds

Holiday condos with beach access

4.93 out of 5 average rating, 206 reviews

A comfortable living area features a neutral-colored sofa, a round dining table, and a ceiling fan. Large sliding glass doors provide access to a balcony, allowing natural light to fill the space and offering views of palm trees outside.

Condo in Tampa

Waterfront Condo - Sunset View of Tampa Bay

4.99 out of 5 average rating, 108 reviews

A waterfront view showcases the community pier lined with palm trees, providing access to the Intracoastal waterway. The nearby building features balconies and patio furniture under blue umbrellas, enhancing the leisure atmosphere. Multiple docks extend into the clear water, inviting relaxation.

Condo in Indian Shores

Blue Sea Renity -All in between Sunrise to Sunset

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, 124 reviews

Renovated Condo! Across the Street From The Beach

4.96 out of 5 average rating, 103 reviews

A heated swimming pool is surrounded by neatly arranged loungers, with palm trees providing shade. A clear sky and vibrant sunset colors reflect on the water's surface. The pool area is enclosed by a black fence, ensuring a private and relaxing environment.

Condo in Largo

Boho Beach Condo

4.75 out of 5 average rating, 250 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

4.95 out of 5 average rating, 126 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

Condo in Clearwater Beach

4.99 out of 5 average rating, 117 reviews

2 King Suites | Stunning Views | Walk Everywhere!