Villa holiday rentals in Madeira Beach

Villa in Indian Rocks 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, 40 reviews

IRB Harbor House Semiprivate Waterfront Pool Villa

IRB Harbor House, your coastal getaway 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 heated 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.

4.95 out of 5 average rating, 134 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!!

5 out of 5 average rating, 147 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"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

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, 154 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.

Villa in Indian Rocks Beach

4.93 out of 5 average rating, 86 reviews

The Emerald Villa, Eco-Luxury by the Sea

Eco-friendly, earth conscious 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.

4.68 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

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.

4.94 out of 5 average rating, 49 reviews

Modern Luxury Villa - Heated Pool Spa, Game Room

Our Luxury Ultra Modern Villa has all the amenities and games you'll need on your vacation. STUNNING backyard with heated pool, spa, fire pit and games. Incredible Game Room with pool table, foosball and ping pong. This villa is in a fantastic location just minutes away from some of the most popular beaches in the country! 5 min - Beach Access 13 min - Indian Rocks Beach (Times are subject to change depending on a traffic) Experience Seminole, Florida with Us and Learn more below!

Villa in Redington Shores

4.91 out of 5 average rating, 142 reviews

Gulf side. 1 house to beach. Peaceful 2 king beds

Construction upgrades complete! 30 second walk to gorgeous beach with amazing sunsets and miles of beachfront. Tucked away on a quiet street, a hidden gem away from busy condos. 1 of 3 units in a small villa on the beach side. Walk to restaurants. Beach towels, chairs & cooler. Washer/Dryer in unit, central AC, Wi-Fi, free parking in front. 2 bedrooms have King beds, 1 bedroom has 2 Twins (this room has W/D and extra sofa). Blackout curtains & comfy mattresses in all bedrooms.

4.9 out of 5 average rating, 123 reviews

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 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.

4.76 out of 5 average rating, 178 reviews

Dolphin Cove Waterfront St. Pete Beach w/ Pool

THIS is the Florida life! A private oasis with a stunning tropical backyard and an oversized SALTWATER pool. Enjoy 140+ ft of waterfront on Bear Creek canal, where manatees and dolphins visit daily! Kayak just 15 minutes to nearby islands. Beaches are a quick 7-minute drive, downtown is 15 minutes away, and shops/restaurants are right across the street. The home is simple and unupdated, but the backyard is a true paradise you won’t forget!

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.

4.98 out of 5 average rating, 41 reviews

[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!

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, 91 reviews

10 minutes to Beaches! Basil House

Your Perfect Florida Getaway! Minutes from all the beaches Pinellas County has to offer! 1G Wi-Fi and a workstation in case you need to work while away. Less than 10 minutes to the beaches, and surrounded by great restaurants. You will enjoy every minute of your visit. Digital Guidebook with local recommendations! Located between St Pete and Clearwater while still close to the beach!

Popular amenities for Madeira Beach villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.86 out of 5 average rating, 110 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

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

Villa in Clearwater

New place to stay

Villa pool in Clearwater|Sleeps 7, Great Location

Villa in Clearwater

Modern 3BR /Private Pool/ 5 Cozy Beds + BBQ

Villa in Redington Shores

4.88 out of 5 average rating, 131 reviews

Gulf side 1 house to beach. Peaceful retreat

4.76 out of 5 average rating, 37 reviews

Newly remodeled-minutes from the beach

A cozy living area is furnished with a gray sofa accompanied by decorative pillows. A light wooden coffee table is centered, with a seashell and decor placed on it. The window allows natural light, complemented by light walls and beach-themed accents.

Villa in St. Pete Beach

Beach Lover's Cove 'Sea La Vie'

Luxury villa rentals

Spacious Pool Villa Just Minutes from the Beach

A serene pool area features a flowing waterfall cascading over textured rocks. The pool water glistens in varying shades of blue, surrounded by palm trees and a spacious patio. Two black lounge chairs are positioned along the poolside for relaxation.

4.91 out of 5 average rating, 102 reviews

Mod Home Heated Pool Resort Backyard 4min to beach

An outdoor space features a basketball hoop and a putting green, surrounded by fresh landscaping. A spacious covered area is seen in the background, providing shade. Palm trees and a clear blue sky enhance the inviting environment.

4.93 out of 5 average rating, 85 reviews

Perfect location 6BR/4BA Pool GameRoom 5 min Beach

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

4.95 out of 5 average rating, 21 reviews

Villa in Clearwater

5BR Pool Villa | Game Room | Near Clear Waterbeach

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.

4.98 out of 5 average rating, 45 reviews

Walk to Beach (4 min), Pool, Private Roof Deck

Villa rentals with a pool

4.97 out of 5 average rating, 29 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

4.94 out of 5 average rating, 52 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.

4.57 out of 5 average rating, 7 reviews

Villa in Belleair Beach

New place to stay

Gorgeous Villa with Heated Pool & Beach Views!

Villa in Indian Shores

New place to stay

Bayview Villa 121 - Quick Walk to Beach!

Villa in Madeira Beach

Vila at Holiday Isles Resort

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