Villa vacation rentals in Madeira Beach

An aerial view showcases a coastal neighborhood along the intracoastal waterway, featuring a single-story home with a gray roof and a landscaped front yard. Palm trees line the driveway, and nearby properties reflect a variety of architectural styles, emphasizing the serene waterfront setting.

5 out of 5 average rating, 38 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

IRB Harbor House, your coastal getaway nestled in the heart of Indian Rocks Beach. This unique shared property concept with semi-private villa boasts 2 cozy bedrooms, 2 modern bathrooms & full size kitchen; perfect for small families, small groups & professionals. Enjoy the convenience of upscale private living with resort style pool on a shared property Whether you're here to soak up the sun or simply relax, Harbor House offers the perfect blend of comfort & convenience for your beach vacation

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.

4.94 out of 5 average rating, 125 reviews

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!!

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

Best kept secret on quiet street beachside away from busy condos. Only 1 house to wide pristine beach stretching for miles Upstairs unit 1 of 3 units ****CONSTRUCTION LOWER UNITS 10/20 FOR 5 WEEKS. Price reflects this. Beach supplies: towels, beach chairs, cooler, beach tent. Walk to restaurants. W/D IN UNIT, Central AC, WIFI, park free Bedrooms: Comfortable mattresses. Black-out curtains. 2 bdrms with king beds. 3rd bdrm is large BONUS ROOM/laundry 2 twin beds, sliding door for privacy

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.

4.97 out of 5 average rating, 144 reviews

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.

4.68 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

Holiday Villas 3 is an ocean front resort community of individually owned villas located between Clearwater Beach & St. Pete Beach. Indian Shores Beach features miles of white sugary soft sandy beaches & pristine turquoise blue waters of the Gulf of America Easy access to many restaurants, bars, nightlife & shops. Check out Johns Pass and try some fresh locally caught grouper at restaurants close by. This property does not have a balcony or direct ocean view but is just steps to beach

4.84 out of 5 average rating, 56 reviews

Pamper Yourself With A High-End Stacay – 1B Home.

Discover a stylish, secluded villa perfect for reconnecting with your loved one. Just 15 minutes from the stunning Indian Rocks Beach, our entire villa offers an exclusive retreat designed for romance, celebration, and memorable special occasions. Guests will also appreciate the fully equipped chef's kitchen. The fenced-in patio features a grill, ideal for outdoor dining and entertaining. The villa also boasts a refreshing private pool nestled amidst tropical shrubbery and bamboo.

A wide view of the intercoastal waterway reveals vibrant turquoise waters and a private dock. Lush greenery and a spacious pool area are visible, featuring a unique shape and several lounge chairs. The serene setting offers an inviting outdoor space for relaxation.

5 out of 5 average rating, 52 reviews

Villa Blanca - Waterfront Midcentury Modern Home

Located in the charming and laid-back neighborhood of Indian Rocks Beach, Villa Blanca is ideally situated to enjoy all the amenities the beach community has to offer. The beautifully renovated mid-century modern waterfront home is completely updated, sparkling clean with a private pool, dock and only a 10-minute walk to the beach. You will also find pickleball courts, a skate board park, children’s playground and a nature preserve boardwalk within a 5 minute walk.BTR 2011

4.95 out of 5 average rating, 65 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

Stay in our 5BR custom-designed home for the ultimate Florida experience. Ideal for family gatherings or social groups with a Heated Pool, Games Room, and excess space for indoor and outdoor lounging. Our fully-renovated house is situated in a tranquil neighborhood just .5 mile away from the Gulf Coast. You have easy access to America's top beaches like St. Pete, Indian Rocks, Madeira, and Clearwater. Our home also has a master bedroom on the first floor for elderly guests.

4.95 out of 5 average rating, 81 reviews

The Emerald Villa, Eco-Luxury by the Sea

Eco-friendly seaside villa. Located just steps from the soft sands of the Gulf of Mexico beach, this exquisitely designed family home offers a luxurious yet sustainable escape. Encased in natural light, 4 bedrooms and 3 baths, the villa sleeps dynamic families and small groups in uncompromising comfort and style and provides all the zen essentials. In-house health suite with gym, infrared sauna and red light therapy available upon request at small additional daily fee.

4.86 out of 5 average rating, 96 reviews

A bright kitchen features a cheerful, colorful wallpaper with a playful design. A traditional farmhouse sink is situated on a light blue countertop, accompanied by various kitchen utensils and knives mounted on the wall. A vibrant yellow door complements the lively aesthetic, inviting natural light.

Villa in Gulfport

Cozy funky duplex with KING bed

Escape to the charming town of Gulfport, Florida, and discover a hidden gem nestled in the heart of this vibrant community. Our eclectic studio offers a one-of-a-kind experience for those seeking comfort, style, and a touch of the extraordinary. The main highlight is the funky wallpaper and the luxurious king-sized bed, adorned with premium linens and plush pillows, ensuring a restful night's sleep after your Gulfport adventures.

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, 112 reviews

A modern living area features a large black leather sectional sofa adorned with decorative pillows, complemented by a polished coffee table. Above, a flat-screen TV is mounted on a light-colored wall. Art pieces showcase scenic landscapes, and natural light filters in through white-shuttered windows.

Villa in Safety Harbor

Villa Italia "Villas by Christine"

Perfect location, Charming Villa!! Guests are loving the newly renovated Villa Italia. Two luxury Masters with separate bathrooms - one upstairs & one down. Within the upstairs bedroom you have a queen size bed along with a full size couch for lounging during the day. We are pet friendly. Please let us know you will be bringing your pet. Pet fee of $100. can be paid beforehand or is due upon arrival.

Popular amenities for Madeira Beach villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Villa in Central Oak Park

4.61 out of 5 average rating, 41 reviews

1Bd-Beach in under 13 mins & Downtown St. Pete

5 out of 5 average rating, 143 reviews

A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.

Villa in Safety Harbor

Villa Key West "Villas by Christine"

A private rooftop terrace features a hot tub, comfortable seating area, and a large umbrella providing shade. The artificial turf enhances the outdoor space, while distant views of buildings and the clear blue sky create a serene atmosphere.

Villa in Clearwater Beach

4.42 out of 5 average rating, 19 reviews

Paradise Cove Townhome 145-3 - Premium Waterfront Community

The exterior of the house is shown, featuring a light yellow façade surrounded by lush green landscaping. Notable elements include palm trees and a manicured lawn, enhancing the welcoming curb appeal. A driveway leads to the entrance, providing ample parking space.

Villa in Logan Gate Village

4.44 out of 5 average rating, 9 reviews

House in a quiet place to rest in Tampa

A charming entryway features a light-colored front door surrounded by large windows and lush tropical plants. The space is paved with square tiles and shaded by a wooden trellis adorned with vibrant flowering vines.

Villa in Dunedin

Unique Villas 3Plex in the Heart of Downtn Dunedin

A fenced outdoor area showcases a clear pool, enclosed by a screen for protection against insects. The pool features steps for easy access and is bordered by smooth concrete, with greenery visible in the background.

St. Pete's Dream Home with Gym and Heated Pool

4.81 out of 5 average rating, 21 reviews

A cozy living area features a light-colored sectional sofa adorned with decorative pillows. Natural light enters through multiple plantation-shuttered windows, highlighting the soft tones of the furnishings. An entertainment unit with a large television and a small decorative table adds functionality to the space.

Villa in Clearwater

Private Villa with Courtyard

A light-filled living area features a comfortable sofa adorned with decorative pillows. A wooden coffee table sits in front, complemented by a small plant. Sheer curtains frame the window, while a ceiling fan offers ventilation. A door leads to the outside, and a workspace is visible in the background.

4.99 out of 5 average rating, 82 reviews

10 minutes to Beaches! Basil House

Luxury villa rentals

4.96 out of 5 average rating, 23 reviews

A spacious heated saltwater pool is surrounded by a screened enclosure, featuring colorful inflatable floats. A playroom is visible with cheerful decor, while a cozy media room offers comfortable seating. The exterior showcases a welcoming home, with a yard perfect for children’s play.

Villa in Dunedin

Family Haven/Kid's Amenities Near Honeymoon Island

4.96 out of 5 average rating, 48 reviews

An outdoor space features a circular fire pit surrounded by several black Adirondack chairs, all set on gravel. The background showcases a heated pool and spa, with a vibrant sunset sky illuminating the scene. The villa and dining area are visible, enhancing the inviting atmosphere.

Villa in Seminole

Modern Luxury Villa - Heated Pool Spa, Game Room

A wooden playhouse stands illuminated with colorful lights, featuring a slide and a set of stairs. The structure is surrounded by lush greenery, providing a playful outdoor space. Notable elements include a pink flamingo and a small white bunny decoration nearby.

Private room in Snell Isle

Private Suite in Luxury Villa near dwntwn St. Pete

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.

4.86 out of 5 average rating, 64 reviews

Best deal in town!

5 out of 5 average rating, 29 reviews

A tranquil pool area is highlighted by a sparkling blue water surface, surrounded by lush greenery. Comfortable lounge chairs are arranged nearby, adorned with striped pillows. A gentle waterfall feature adds a serene touch, while a privacy fence encloses the space.

Villa in Bay Crest Park

(BAYC) Heated Pool Villa. Boat rental available

4.9 out of 5 average rating, 40 reviews

6BR Waterfront • Heated Pool • Hot Tub • Game Room

Villa in Clearwater Beach

A rooftop terrace is shown with two lounge chairs and a small table. A large umbrella provides shade, while a view of the waterfront and city skyline is visible in the background. The sky displays soft hues of purple and pink, enhancing the serene setting.

4.97 out of 5 average rating, 39 reviews

4 min Walk to Beach, Pool, Roof Deck

A private pool area features clear water surrounded by a spacious deck. Tall palm trees offer shade along one side, while lounge chairs are positioned nearby, creating a serene outdoor space for relaxation.

4.82 out of 5 average rating, 17 reviews

Modern Pool Estate, Beach, Downtown - seasonal

Villa rentals with a pool

4.94 out of 5 average rating, 47 reviews

The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.

Villa in Palm Harbor

Villa Luxe~Heated Saltwater Pool~Near Beaches

Villa in Tampa

Beyond luxury and architecture.

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.

4.79 out of 5 average rating, 169 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

Villa in Palm Harbor

4.75 out of 5 average rating, 8 reviews

Dream Home Family Retreat | 4BR, Near the Gulf

4.89 out of 5 average rating, 19 reviews

A modern kitchen features wooden cabinetry and a granite countertop, complemented by stainless steel appliances. Red chairs are placed around a dining area visible in the background, with decorative wall art enhancing the space. Natural light filters through the windows, providing a bright atmosphere.

Villa in Treasure Island

Luxury waterfront in the heart of treasure island

4.89 out of 5 average rating, 85 reviews

A spacious lawn surrounds the villa, featuring tropical landscaping and a patio area with seating. A pool is visible alongside the well-maintained pathway, leading to the water. The structure showcases large windows that invite natural light, presenting a warm outdoor setting.

Villa in Bay Crest Park

The Palm Island Villa Luxury 4 BDR Waterfront Home

Villa in Palm Harbor

5 out of 5 average rating, 3 reviews

Family-Friendly 3BR Getaway Saltwater pool

A bright outdoor area features a sparkling pool surrounded by sun loungers and a patio with stylish landscaping. The property includes a composite dock and is bordered by greenery, offering a tranquil view of the Intracoastal waterfront.