Villa holiday rentals in Holmes Beach

4.94 out of 5 average rating, 127 reviews

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

A cozy bedroom features a spacious bed with light bedding, accented by decorative pillows. Natural light streams through sheer curtains by the window, illuminating the room's soft blue walls. A wooden dresser and a ceiling fan add functional elements to the friendly space.

4.97 out of 5 average rating, 37 reviews

Starfish House - 2bed/2bad

An Anna Maria Island Vacation to remember is waiting for you at Starfish Beach #4. This charming complex is small and quiet, perfect for a relaxing beach getaway. A shared pool is available in the courtyard. You'll enjoy being just steps from the Anna Maria Public beach access. With a short walk, finding your place in the sand each morning will be easier than ever! 50 yards to the BEACH! Bed size: 1 K, 1 Q, sleeper Baby accessories available for rent. Snoo Bassinet high chair pack and play

An aerial view showcases the studio villa nestled among lush greenery, with the expansive Manatee River visible in the background. The nearby dock and boardwalk line the water, providing access to recreational activities, while the vibrant greenery enhances the serene outdoor atmosphere.

5 out of 5 average rating, 59 reviews

Sunswept Villa 4 - Waterview! 15 min to AMI beach

Welcome to this unique & sundrenched getaway. With views of the Manatee River & situated steps from Mineral Springs Park & Riverwalk, you have quick access to fishing, beaches, dining, shopping, parks, & historical sites. This updated studio villa has a king size bed, full kitchen and stocked coffee/tea bar. There are lots of windows & front patio w/ river/park views. The back is lush with century old Live Oak Tree, waterfall, gardens, hammock & pool. Let your pup play in the fenced dog area.

4.9 out of 5 average rating, 218 reviews

A spacious living area is highlighted by a large sectional sofa and a wooden coffee table. A TV sits atop a media console, while glass doors provide access to the outdoor patio, allowing natural light to fill the room.

Villa in Lido Key

Entire Standalone Villa,1.2k sf,1 block Lido Beach

Welcome to our cute, spacious, sun filled and newly renovated Beach Villa. A Happy place for sandy feet, friends, and family. The Villa is located 1 block away from world famous Lido Beach, a 7 min walk to St Armand's Circle, and a short 3 mile drive to grocery shopping & the excitement of downtown Sarasota. The 2 bdr villa comfortably sleeps up to 6 people and features a private outdoor patio, spacious dining area, in-unit washer/dryer & dedicated parking. Come enjoy a taste of paradise!

4.97 out of 5 average rating, 146 reviews

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

4.88 out of 5 average rating, 294 reviews

A single-story home is surrounded by greenery and palm trees, showcasing a light green exterior. A narrow pathway leads to the entrance, flanked by decorative planters. The white fence adds charm and defines the front yard, with large windows allowing natural light into the interiors.

Villa in Laurel Park

Duplex - just mins to Siesta Beach - Pet Friendly

This is a 2/1 in Sarasota's Historic Laurel Park that offers a great downtown and beach experience! Walk/bike to historic downtown with shops, restaurants, bars, boutiques, parks, and music/theater. Minutes from the best beaches in the U.S. Enjoy the lanai & fenced backyard for privacy . Grill & enjoy your favorite beverage while watching your favorite show on the lanai ! Enjoy taking your pet for a walk & check out the historic homes in the area! Short term rental number VR24-00222

5 out of 5 average rating, 116 reviews

A relaxing outdoor space features a lounge chair adorned with a striped towel and a wide-brimmed hat. A tray holds a refreshing drink beside the crystal-clear pool, surrounded by lush tropical foliage and a colorful float visible in the water.

Villa in Arlington Park

Tropical Luxury Villa: Pool, Game Room, Near Beach

Welcome to your tropical luxury escape! Spacious living flows to the heated pool, game room and sunny patio—perfect for family fun. Bedrooms: 4 private suites, plush linens and blackout shades ensure restful nights. Location: Quiet neighborhood just minutes from the sandy beach, dining and shopping hotspots. Heated pool & sun loungers Arcade-style game room Fast Wi-Fi & 5-star cleanliness Pet friendly with fenced yard Have questions? We reply in under an hour—book your stay today!

4.9 out of 5 average rating, 117 reviews

Villa in Largo

The Tropical Oasis, w/ Solar Heated Pool and Games

Welcome to your private, tropical escape! Unwind by the solar-heated pool in a screened, mosquito-free lanai. FUN & GAMES: Enjoy Billiards (Pool Table) 🎱, Foosball, Cornhole, board games, and 3 Smart TVs 📺. PRIME LOCATION: Only 5 min 🚗 to Indian Rocks & Bellaire Beach, FL Botanical Garden, and dining. Essentials: 🌞 Heated Swimming Pool (Private!) 🎮 Billiard Table / Foosball Table / Cornhole / Boardgames and more! 🛏️ 4 Queen/Full Beds 🧺 Beach Amenities

A serene outdoor space is showcased, featuring lush green palm and banana trees gently swaying near a calm body of water. Sunlight reflects off the water's surface, surrounded by a natural landscape of tall grasses and distant trees under a clear blue sky.

4.76 out of 5 average rating, 109 reviews

Lakefront 2BR • Perfect for IMG & Long Stays

Wake up to peaceful lake views at this centrally located 2BR/2BA Bradenton duplex—just 3 minutes to IMG Academy, 10 minutes to Downtown Bradenton, and 15 minutes to Anna Maria Island. Enjoy a fully stocked kitchen, fast Wi-Fi, Smart TV, in-unit laundry, and off-street parking. Perfect for families, athletes, remote workers, or long-term guests looking for comfort, convenience, and easy access to beaches, dining, shops, and SRQ Airport.

5 out of 5 average rating, 32 reviews

An outdoor patio area features a private pool surrounded by a spacious deck. A seating arrangement with chairs and a table is positioned nearby, along with a sauna. The setting is complemented by lush green grass and a colorful sunset sky.

Villa in Seminole

[TRENDlNG] Modern 5BR Pool Villa + Arcade & Sauna

The Ultimate Vacation Awaits! Welcome to your home away from home—where comfort, fun, and relaxation all come together. Whether you’re here to unwind, explore, or make memories with friends and family, this place has you covered. Just 5 minutes from Madeira Beach and a short drive to Indian Rocks, Indian Shores, and Redington Shores—enjoy quick access to some of Florida’s best white-sand beaches and crystal-clear Gulf waters!

5 out of 5 average rating, 27 reviews

Beachfront Paradise! Ground level with Heated pool

Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

4.88 out of 5 average rating, 114 reviews

Florida Living

This House has 3 bedrooms, 2 bathrooms, kitchen, living & dining, Pool, GAME ROOM (Pool Table, Fossball ,Bar ) 65 inchTV, wireless internet. It is conveniently located near local attractions, yet secluded and quiet. If you are looking for a private escape in a peaceful setting with comfortable furnishings and a lot of fun games this property is for you and your family .

Popular amenities for villa rentals in Holmes Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.9 out of 5 average rating, 10 reviews

Anna Maria Island Beach Getaway – Sleeps 6

4.75 out of 5 average rating, 20 reviews

The front entrance of a light blue house is framed by a manicured lawn and lush greenery. A clear pathway leads to the door, bordered by decorative stones and various potted plants. Tall trees provide shade and an inviting atmosphere.

Villa in Bayou Oaks

Tiki Bella Villa (Entire home with Pool)

4.68 out of 5 average rating, 65 reviews

A large heated swimming pool is surrounded by lounge chairs and tiki huts, set against the backdrop of a sandy beach and the shimmering Gulf waters. Sunlight reflects off the water, creating a tranquil atmosphere for relaxation and leisure.

Villa in Indian Shores

Relax just steps from beach & Gulf of America

A villa with a light-colored exterior features a spacious driveway made of pavers. Lush tropical landscaping adds color, while a large parking garage is visible on the right side. In the background, a multi-story building is partly shown under a partly cloudy sky.

5 out of 5 average rating, 9 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

A private patio area is displayed with a round table surrounded by six chairs and a large umbrella. Two lounge chairs are positioned nearby. The exterior features large windows reflecting a vibrant sunset, enhancing the tranquil atmosphere.

5 out of 5 average rating, 20 reviews

Waterfront in Paradise

4.75 out of 5 average rating, 16 reviews

A modern kitchen features white cabinetry and a spacious granite countertop. Stainless steel appliances, including a microwave and oven, are visible. A sink with a sleek faucet is positioned near a window, and a coffee maker is placed on the counter.

Villa in Ruskin

*Modern 2/2 Cottage with Spacious Backyard*

The outdoor pool area features a spacious swimming pool alongside a hot tub. Surrounded by tall trees, the space offers a relaxing atmosphere with lounge chairs and umbrellas positioned around the pool deck. Clear blue skies enhance the inviting setting.

4.73 out of 5 average rating, 11 reviews

Charming 2/2 Village des Pins close to Siesta Key

4.78 out of 5 average rating, 172 reviews

A spacious saltwater pool stretches across the backyard, bordered by a paved area featuring lounge chairs. Lush greenery, including palm trees and a nearby canal, enhances the serene outdoor setting under a clear blue sky.

Villa in St. Petersburg

Dolphin Cove Waterfront St. Pete Beach w/ Pool

Luxury villa rentals

A sunlit wooden deck is lined with blue lounge chairs, facing the expansive sandy beach and the Gulf of Mexico. Gentle waves can be seen lapping at the shore, under a sky filled with fluffy clouds. The inviting atmosphere offers direct access to the beach.

A Wave From it All managed by Beach Retreats

5 out of 5 average rating, 79 reviews

A serene outdoor pool area is enclosed by a screened structure, allowing for a private retreat. Sun loungers are positioned beside the clear, inviting water, and lush greenery surrounds the pool, enhancing the tranquil setting.

Villa in Tampa

Luxury home in the heart of South Tampa & POOL!

Villa in Redington Shores

A sandy pathway leads through palm trees and lush greenery toward a wide beach. The ocean's calm surface reflects a bright blue sky with scattered clouds. A beach umbrella is visible to the left, suggesting a serene, inviting atmosphere.

4.92 out of 5 average rating, 138 reviews

1 House to beach! Peaceful beachside getaway

4.5 out of 5 average rating, 20 reviews

Lemon Fish Villa! Walk to Beach and Pool!

A private pool area is surrounded by tropical greenery, featuring a wooden deck with smooth steps leading down to the water. Bright lounge chairs sit nearby, and pool floats are casually draped over the railing, inviting relaxation and enjoyment.

4.76 out of 5 average rating, 117 reviews

5 min to Siesta Key, Heated Pool, Grill, WiFi

4.86 out of 5 average rating, 64 reviews

An open dining area features a wooden table set for six, with white plates and dark napkins. A stylish light fixture hangs above, illuminating the space. The adjoining kitchen area includes dark cabinetry and modern appliances, offering a seamless flow between dining and cooking.

Villa in Largo

Best deal in town!

A private pool is framed by wooden fencing, providing a secluded outdoor area. Sun loungers are positioned poolside, inviting relaxation. The clear water glistens under sunlight, while a few trees provide greenery in the background.

4.75 out of 5 average rating, 4 reviews

2 back-to-back Villas for 12 with 2 private pools

4.95 out of 5 average rating, 66 reviews

A heated pool is surrounded by comfortable loungers and shaded by a stylish cabana. A spacious patio area features outdoor seating, while lush greenery and tall trees create a serene backdrop under the clear blue sky.

Villa in Seminole

5 BR Luxury Beach Villa: Heated Pool & Games Room

Villa rentals with a pool

An outdoor area features a spacious patio with a large dining table and several chairs, set among lush tropical greenery. A pool is visible nearby, surrounded by lounge chairs. A spiral staircase leads to an upper level, adding architectural interest to the space.

Villa in Anna Maria

4.71 out of 5 average rating, 7 reviews

Bean Point Residence Unit B by SeaBreeze Vacation

5 out of 5 average rating, 16 reviews

Villa in Siesta Key

The Beachwood Hideout | SK Collection

A large, inviting pool is surrounded by lush greenery and tall pine trees. Several lounge chairs are visible around the pool area, with bright sunlight reflecting off the clear water. The depth marker indicates a shallow end of 3 feet 6 inches.

4.97 out of 5 average rating, 38 reviews

Vacation Villa/Resort Pool 4 miles to Siesta Key

A sparkling pool is featured within a screened-in area, surrounded by brick pavers. Comfortable lounge chairs are positioned beside the water, while a dining table with chairs is visible in the shaded area. Lush greenery is present in the background, enhancing the outdoor setting.

5 out of 5 average rating, 4 reviews

Florida Villa Sunrise - 4 Bedroom Home with Pool

A modern home is depicted, featuring a light exterior with multiple large windows and an inviting entrance. Lush greenery and landscaped gardens frame the property, providing a serene atmosphere. A spacious driveway leads up to the house, complemented by a clear blue sky.

Villa

Villa Summerwind 3bed/2bath pool villa

4.85 out of 5 average rating, 41 reviews

Heated Pool & Spa • Outdoor Kitchen/Theater/Games

A two-story villa features a light blue exterior and a covered front porch. Two outdoor chairs are positioned on the porch, with tropical landscaping surrounding the entryway. Windows are adorned with white trim, allowing natural light to fill the space.

4.7 out of 5 average rating, 20 reviews

Close to beach, shops and restaurants!

A light and airy living space is presented, featuring a neutral sofa and a glass coffee table. Natural light pours in through double doors, leading to an outdoor area. A small TV stand holds a flat-screen television, while soft lighting is provided by a lamp on an adjacent table.