Holiday rentals with a fireplace near Anna Maria Island

A spacious living area features a large sectional sofa, offering ample seating. A contemporary chandelier hangs from the ceiling, while a light-colored coffee table sits at the center. In the background, a modern kitchen is visible, accentuated by sleek cabinetry and bright lighting.

4.96 out of 5 average rating, 109 reviews

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

An inviting outdoor lanai is shown, featuring comfortable seating with colorful cushions. A wooden coffee table holds glassware, while a heated pool glistens in the background, surrounded by lush greenery. The screened area offers a seamless connection to the tranquil outdoor environment.

5 out of 5 average rating, 101 reviews

Heated Pool-Game Room-EV-Near AMI Beaches/IMG!

Enjoy easy living in this updated tropical home! Your private screened lanai is perfect for seamless indoor/outdoor relaxing, with a heated pool and covered dining/lounge area with a 58" outdoor TV! The interior of the home is bright and open with cheerful coastal decor and plenty of room to spread out. We provide everything you need with a well-stocked kitchen, gas grill, game room, beach gear, towels, EV Charger! In a quiet neighborhood with quick access to AMI beaches IMG, parks, and trails!

4.98 out of 5 average rating, 166 reviews

SLeePs18+2babyCrib-Hotub-2kingSuites-IMG-picklbal

We sleep 18 adults comfortably plus have 2 baby cribs, so can sleep 20! 5 BEDROOMS!!! NEW PICKLEBALL COURT- new mini golf course- Kids playground- Hot tub- bunks with tube slide- Arcade room- pool table and more! ▪️2Game Rooms ▪️2KingSuites ▪️7miles to Beach ▪️Blackout curtains ▪️BabyMonitor▪️Crib on wheels AND PackNPlay ▪️HighChair ▪️beach chairs▪️pool table▪️hot tub ▪️pickleball▪️RokuTV’s▪️Self Checkin ▪️AirHockey ▪️Grill ▪️FirePit ▪️Washer/Dryer ▪️CoffeeBar▪️Cable ⭐️No Checkout List⭐️

4.96 out of 5 average rating, 23 reviews

The Florida Rooms

NEW POOL/SPA. Just 10 minutes from the beach, The Florida Rooms is a 3BR, 2BA retreat with NEW RESORT POOL & SPA, outdoor dining and living space, premium beds, rain showers, a full kitchen, and dining for 8. Extra sleeping includes a queen sofa bed and Pack ’n Play. Enjoy a pool table, ping-pong, board games, outdoor string lights, and a fire pit. We include beach gear—chairs, towels, umbrella, and wagon—for easy fun in the sun. Comfort, charm, and convenience await! Pool/spa heating included!

A tranquil outdoor space features a heated pool surrounded by stone pavers. Comfortable lounge chairs are positioned nearby, and a modern fire pit offers seating. The restored stone house stands in the background, framed by palm trees under a clear blue sky.

4.97 out of 5 average rating, 31 reviews

100 yr Old Stone Home + Pool + 9 miles to beaches

Charming 100-Year-Old Restored Stone House with Italian Flair – Close to Beach & Downtown! Welcome to your dream getaway! This beautifully restored 100-year-old stone home blends old-world charm with modern luxury. Inspired by the elegance of Italy, this unique retreat is just minutes from the beach and vibrant downtown Bradenton. The home has abundant natural light and has 2 bedrooms, 2 half baths and a spacious yard! You will love the heated pool and outdoor firepit for year-round relaxing.

The outdoor area showcases a heated saltwater pool surrounded by lounge chairs and a covered seating area. A manicured artificial turf putting green is prominently featured, providing a playful touch to the spacious backyard, which is framed by lush landscaping and bright skies.

4.79 out of 5 average rating, 365 reviews

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

In the foreground, a hammock rests on a sturdy stand, placed on lush green grass. Nearby, two kayaks in vibrant red and blue are positioned side by side, with a glimpse of a boat dock visible in the background, surrounded by tropical vegetation.

5 out of 5 average rating, 103 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

A charming exterior view of the property is highlighted, showcasing a welcoming entrance with a decorative stone feature. The path leads to a well-lit entrance, framed by vibrant landscaping and palm trees, creating an inviting atmosphere for guests.

4.96 out of 5 average rating, 316 reviews

Casa del Río! Beaches, IMG, Boating, and Riverwalk.

Welcome to "Casa del Rio" in Bradenton, FL featured in hit TV Show 90 DAY FIANCÉ! Location less than 15 minutes from the beach, IMG, Downtown, Riverwalk, Pirate City, and popular restaurants. Main Road takes you straight to Beach NO turns! I've thought of everything to make your stay as comfortable as possible. Keyless check-in experience with Smart Lock. Amazon Fire TV Free movies and TV Shows. Netflix ready. Brazilian Hammock under a Tiki Hut. Coffee and Tea station. Beach gear.

4.98 out of 5 average rating, 60 reviews

A covered porch features wicker seating arrangements, including a white couch and two armchairs, inviting relaxation. Decorative pillows and a colorful throw add comfort to the space. Light streams through large windows, creating a bright and airy atmosphere, with an inviting view of the surroundings.

Cottage in Bradenton

Seagull Cottage Cortez, Sleeps 6, Walk to Beach

Seagull Cottage! A charming family/pet friendly cottage in a unique neighborhood a combination of homes/mobile homes. Boat marina and our private beach side park on Palma Sola Bay it’s just 3 min walk, where you can Picnic, kayak, fish, swim or just sit and watch for dolphins/ manatees, plus it’s dog friendly. Seagull Cottage is Less than 2 miles to Anna Maria Island. One of our main focuses is to offer perfectly clean rooms to ensure you have a relaxed /comfortable holiday.

5 out of 5 average rating, 15 reviews

Home in Holmes Beach

Americana AMI Lighthouse 3BR w/pool + rooftop deck

Discover this unique lighthouse vacation rental w/private pool on Anna Maria Island. The Lighthouse has 3 bedrooms, 2.5 baths with an open plan living/kitchen/dining which is perfect for a family vacation or getaway with friends. Located in Holmes Beach, the home is only a short walk (approx. 6 min) to the beautiful Gulf beach. The house has been lovingly decorated with retro memorabilia creating a vintage americana aesthetic. Enjoy our budget-friendly pricing.

4.86 out of 5 average rating, 180 reviews

Tipsy Flamingo | POOL • HOT TUB • FIRE PIT • GAMES

Dive into the curious home of Tipsy Flamingo. The tropical fever dream you didn’t know you needed! Stay in a historic home bursting with fluorescent colors, a pink-tastic Flamingo Suite, a wild Jungle Room, and a chill coastal Surf Den. Outside, swing under the pergola, battle it out in giant chess, soak in the hot tub, lounge by the fire pit, and float in the sparkling pool on your honorary pink flamingo throne. Pure fun, pure vibes, pure madness! 🦩

Apartment in Indian Rocks Beach

A bright living area features a comfortable light-colored sofa and armchairs, complemented by a decorative round coffee table. Large glass doors provide an unobstructed view of the beach and palm trees outside, allowing natural light to fill the space.

4.97 out of 5 average rating, 154 reviews

Private Ocean View Beach Retreat with Balcony

Only steps from the beach, this newly updated and perfectly located beach condo is your luxury getaway. The large bedroom, lofty living area and modern open kitchen, as well as the generous balcony with direct view of the Gulf will make you never want to leave again. This condo is better equipped than your average vacation rental and comes with your private daily sunset spectacle. Continue to read for more...

Popular amenities for rentals with a fireplace near Anna Maria Island

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

A tiki bar with thatched roofing is showcased, featuring a wooden bar adorned with colorful tiki carvings. A sign reading 'Attitude Adjustment Time' is visible, with comfortable seating nearby. The private pool can be seen in the background, enhancing the tropical atmosphere.

4.93 out of 5 average rating, 85 reviews

Pool + Tiki Bar + Pickleball + Anna Maria Beaches!

5 out of 5 average rating, 53 reviews

The Sanctuary - Elegant Family Getaway

A tranquil pool area is highlighted by clear, blue water, gently illuminated in soft shades. Comfortable lounge chairs are positioned nearby, surrounded by lush greenery and decorative lighting. Soft sunlight casts a warm glow over the scene, creating a relaxing environment.

5 out of 5 average rating, 25 reviews

Paradise Inn

The living area features a sectional sofa and armchairs in calming tones, complemented by a wooden dining table with high chairs. A built-in television unit is accented by decorative shelves. Natural light filters through large windows, and a ceiling fan adds to the comfort.

4.93 out of 5 average rating, 72 reviews

NEW! Casa Corallo ● At Anna Maria Island Beaches

A clear blue pool reflects the sky, with four white lounge chairs arranged nearby on a sunlit patio. Lush green grass surrounds the pool area, complemented by a large tree offering shade in the background. The scene conveys a serene outdoor space for relaxation.

4.91 out of 5 average rating, 140 reviews

Palma Sola Pool Home, minutes to AMI

5 out of 5 average rating, 21 reviews

A spacious living area is filled with natural light from large windows. A comfortable sectional sofa is arranged with decorative pillows, complemented by a wood coffee table at the center. Two soft reclining chairs are positioned nearby, contributing to the inviting atmosphere.

Home in Holmes Beach

Eileen’s house- steps to the beach.

An aerial view of a spacious backyard features an oversized heated saltwater pool surrounded by lounge chairs and umbrellas. A hot tub is positioned nearby, offering convenience for relaxation. Lush greenery and palm trees contribute to a private and inviting outdoor space.

4.9 out of 5 average rating, 60 reviews

FREE HTD Pool | Mural | Porch | Fire Table | 2 K

4.85 out of 5 average rating, 13 reviews

NEW Waterfront | Heated Pool | Kayaks

Apartment rentals with a fireplace

Flat in Indian Rocks Beach

A spacious balcony offers a panoramic view of the Gulf of Mexico, with a high-top glass bar and two high chairs. The sandy beach and calm ocean stretch out beyond, with distant silhouettes of beachgoers enjoying the shoreline.

4.96 out of 5 average rating, 54 reviews

Direct Beachfront 2B, Large Balcony w/ Oceanview

5 out of 5 average rating, 37 reviews

Flat in Madeira Beach

Gulf View Penthouse | Steps to Beach + Johns Pass

5 out of 5 average rating, 29 reviews

A modern living area is depicted, featuring a large flat-screen TV mounted on the wall above a sleek electric fireplace. The kitchen showcases light wood cabinetry and a tile backsplash. A door with a decorative glass insert leads outside, enhancing the open feel.

Flat in Largo

Tropical Vibes by Indian Rocks Beach

4.94 out of 5 average rating, 48 reviews

Aerial view of a wide beach features soft white sand and gentle waves lapping at the shore. The water displays a gradient of turquoise to deep blue, with scattered footprints in the sand. The horizon meets a clear sky, enhancing the open coastal atmosphere.

Flat in Longboat Key

Turtle walk - Next to 5 top eats & Beach

4.93 out of 5 average rating, 75 reviews

A hanging chair, featuring a soft, cushioned seat, is situated on the balcony, offering direct views of the ocean. The expansive seascape and sandy beach are visible in the background, with a clear blue sky enhancing the serene atmosphere.

Flat in Indian Shores

Luxury Ocean Front Duplex

4.82 out of 5 average rating, 182 reviews

A tranquil shoreline is captured, featuring soft white sand in the foreground and gentle waves lapping at the edge. Sunlight sparkles on the water, creating a shimmering effect, while the horizon meets a clear blue sky dotted with wispy clouds.

Flat in Treasure Island

COZY BEACH HOUSE 2 BEDROOM

4.95 out of 5 average rating, 119 reviews

A spacious bedroom features a plush king bed with a light-colored blanket and two dark nightstands on either side. Vertical windows offer natural light, while neutral gray walls and wood flooring create a calm atmosphere.

Flat in Clearwater

Relaxing beach gateway

5 out of 5 average rating, 18 reviews

An aerial view captures a vibrant beach scene with clear turquoise waters lapping against a sandy shore. The landscape showcases a variety of beachfront buildings and leisure activities, including sunbathers and beach umbrellas, under a bright blue sky with fluffy clouds.

Flat in Madeira Beach

Upscale, cozy and coastal condo!

Villa rentals with a fireplace

A modern living space is shown, featuring a comfortable black sofa and a cozy area rug. A large television is mounted on a stylish media unit, with light streaming in from nearby windows. A dining area with a small table and chairs is also visible.

5 out of 5 average rating, 43 reviews

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach

Villa in Indian Rocks Beach

4.98 out of 5 average rating, 42 reviews

NEW! Waterfront Hot Tub, Heated Pool, & Golf Cart

4.98 out of 5 average rating, 55 reviews

Luxury 4-Bedroom Pool Retreat Near Siesta Key

4.88 out of 5 average rating, 17 reviews

A clear swimming pool rests within a screened enclosure, surrounded by tropical greenery. Comfortable lounge chairs are positioned by the water's edge, inviting relaxation. The pool features a connected hot tub, offering options for leisure and enjoyment.

Villa in Wimauma

Coastal Farmhouse & Pool

A vibrant outdoor scene showcasing a poolside setting with plush lounge chairs and colorful pool floats. A straw hat and sunglasses rest on a striped towel next to a wicker table adorned with tropical-themed items. Refreshing drinks and fruits are nearby, surrounded by lush greenery.

5 out of 5 average rating, 41 reviews

Luxury Pool & Game Retreat • Close to Beaches

5 out of 5 average rating, 67 reviews

Aerial view showcases the property surrounded by lush greenery, with water views of the Manatee River. The image captures the nearby fishing pier, outdoor spaces, and proximity to the river, emphasizing the serene landscape and natural beauty of the area.

Villa in Bradenton

Tranquil Tide Villa - Waterview! 15 min to beach

4.9 out of 5 average rating, 92 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 Tampa

The Palm Island Villa Luxury 4 BDR Waterfront Home

The living area features a green sofa adorned with decorative pillows, paired with a round coffee table on a jute rug. A warm brick fireplace complements the space, which opens up to the pool area through large windows framed by sheer curtains.

4.75 out of 5 average rating, 271 reviews

Perfect Location w/ pool -close to beach or DT!

Other holiday rentals with a fireplace

5 out of 5 average rating, 15 reviews

Bradenton Heated Pool Home Near IMG & Beaches

4.97 out of 5 average rating, 98 reviews

The exterior of the beach house is depicted, showcasing a blue structure with a metal roof surrounded by tropical landscaping. A gravel driveway leads to the entrance, flanked by palm trees and vibrant foliage, emphasizing the inviting coastal atmosphere.

Home in Longboat Key

Beautiful Beach House

Holiday home in Bradenton

The image showcases a saltwater pool surrounded by a manicured grassy area. Two aqua-colored loungers are positioned near the pool, while a bright umbrella adds shade. The duplex structure features multiple balconies and a spacious outdoor area, creating an inviting atmosphere for relaxation.

4.92 out of 5 average rating, 38 reviews

Manatee Manor

Apartment in Holmes Beach

4.75 out of 5 average rating, 4 reviews

2 bedroom condo across beach Anna Maria Island

4.96 out of 5 average rating, 57 reviews

Near Anna Maria & IMG—Chic & Renovated—Fenced Yard

4.94 out of 5 average rating, 71 reviews

5 min AMI•MaySpecial•FreeHeatdPool•Hot Tub•FirePit

4.97 out of 5 average rating, 34 reviews

Family Fun House with Peloton, Pool & Games