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House holiday rentals in Anna Maria Island

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Top-rated house rentals in Anna Maria Island

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Home in Holmes Beach

4.87 out of 5 average rating, 103 reviews

New Golf cart + 4bd/3b w pool/2100 sq ft home

Urban Oasis is a privately owned 2100 sq ft 4 bd, 3 bth on Anna Maria Island. 4 minute walk on a quiet residential street to walk to the beach.This home features grey blue hues, coastal furniture, driftwood accents, themed rooms and designer accents. A brand new 2024 6 str golf cart is included in your rental as well as a premium linen service including all towels and linens. Urban Oasis is truly a turnkey Vacation Rental! We also have a second property, Urban Oasis Too, if you like our style!

Guest favourite

Home in Holmes Beach

4.96 out of 5 average rating, 80 reviews

Stunning Beach Home! Walk to Beaches, Gulf Views

Amazing Location on Holmes beach, just steps to the water! Incredibly built home sets the highest standards of luxury living. It's the ideal retreat with expansive views of the outdoors from the moment you enter. Open concept and large sliders throughout creates the perfect indoor-outdoor lifestyle. Spend the day lounging in the resort-style heated pool w/spa, then enjoy drinks at sunset on the rooftop deck with wet bar, and breathtaking views of the Gulf of Mexico. Leaving this beauty is tough

Guest favourite

Home in Bradenton

4.94 out of 5 average rating, 251 reviews

Home near Anna Maria Beach w/ Hot Tub + Fire Pit

* Place is ready & available post Hurricane Milton, with 5 Star review from recent guest Come find a space away in this 1 bedroom Guest House with a private patio and inflatable hot tub located less than 15 Minutes away from Anna Maria Island Beach. Enjoy all that the area has to offer, and come home to the private ambience of an outdoor fire pit and relaxing hot tub, or play a fun game of corn-hole on the back patio. The home is a quaint 627 square feet in a safe and friendly neighborhood

Guest favourite

Home in Holmes Beach

4.97 out of 5 average rating, 128 reviews

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly (to 35 lbs) in a great location 5 min. walk to the beach. Private lagoon-style *heated* pool amid lush landscaping with gorgeous rock waterfall. Fully updated kitchen, 60-inch Sony HDTV, 55'' Samsung Frame TV, Italian leather reclining sofas, BBQ, beach gear, updated bathrooms, three king bedrooms. Classic Florida one-level home - no stairs. Managed directly by owners. No crazy fees!

Guest favourite

Home in Sarasota

4.96 out of 5 average rating, 142 reviews

Sarasota Florida -Wild Orchid Creek Cottage Home

Come enjoy old Florida living at this completely renovated cottage style home on nearly seven acres. Relax and unwind in this 1000 square foot private home with king bed and queen sleeper to accommodate up to four people. Open concept living, dining room and full kitchen. Laundry facilities available. Equipped with WiFi and direct tv. While enjoying the private backyard space, it is common to spot abundant wildlife and wildflowers. Wild orchids in many of the oak trees bloom in early summer.

Guest favourite

Home in Anna Maria

4.78 out of 5 average rating, 188 reviews

Charming Beach house amongst huge Banyon Trees

Charming bright beach house set amongst grand Banyan trees on tip of Anna Maria. 3 min's stroll over a small fishing bridge to historic Pine Ave w/ quaint eateries and shops. Huge fenced yard voted "A Tropical Paradise" Porch sits among huge banyan trees with native birds. 7 min’s walk to bay front beach or rod and reel pier for fresh meals, cocktails, fishing w/ equip & bait supplied, from there stroll along The beach to "Bean Point" voted 1 of the most beautiful beaches in the world.

Guest favourite

Home in Bradenton

4.89 out of 5 average rating, 104 reviews

Amazing Game Room-86°Pool/Spa-Beaches-Dog Friendly

Enjoy with your whole family at Villa Delfino, a single family home in the heart of beautiful Bradenton. It is a one-of-a-kind fully enclosed, dog friendly outdoor space with a HEATED pool, hot tub, BBQ grill, fire pit, lounge chairs and tiki hut. The home is located just 6 miles to Anna Maria Island with some of the most gorgeous beaches in the world. We supply beach gear including towels, chairs, umbrella, boogie boards, etc. Inside we offer 2 en suites, 1 with a KING bed, FUN Game room.

Guest favourite

Home in Indian Rocks Beach

4.98 out of 5 average rating, 119 reviews

Beachfront Bungalow w/ Pool & Hot Tub in IRB

Beach front house with a saltwater pool! This 2 bedroom, two bath house is equipped with a newly renovated kitchen and new appliances. You will have your own private beach access with 2 outdoor showers. The outdoor dining area is perfect for dinner under the sunset. We are stocked with beach chairs, umbrellas, pool/beach toys, & floats. Close to parks, restaurants, & across the street from a small grocery store. Perfect for families or couples looking for a getaway in the sunshine state.

Guest favourite

Home in Anna Maria

4.97 out of 5 average rating, 61 reviews

Steps to the Beach! Pool/spa! Golf Cart Included

Newly renovated elevated home on the prestigious north end of the island. There is over 2100 sq. ft of living area in addition to the expansive outdoor space including a large saltwater pool/spa, outdoor TV and seating area, outdoor dining area for 10, lawn games and numerous balconies both covered & uncovered. The house is across the street from the Bayfront Park and a 7 minute walk to the world renowned Bean Point. We have also included bikes & a 6 person golf cart for your stay.

Guest favourite

Home in Bradenton Beach

4.97 out of 5 average rating, 159 reviews

BACK Jan 1! Newly Renovated! STEPS 2 Private Beach

NEW Pics Coming! Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Guest favourite

Home in Bradenton Beach

5 out of 5 average rating, 46 reviews

Beach front! Trolley/Sunsets/Pier/Restaurants!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Guest favourite

Home in Bradenton

4.91 out of 5 average rating, 350 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for house rentals in Anna Maria Island

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 173 reviews

Sea AMI

Guest favourite

Home in Holmes Beach

4.93 out of 5 average rating, 14 reviews

Sweet Sea Life - just a short walk to the beach

Guest favourite

Home in Bradenton Beach

5 out of 5 average rating, 44 reviews

AMI*Steps to the beach-Modern luxury POOL SPA

Guest favourite

Home in Holmes Beach

4.99 out of 5 average rating, 155 reviews

Captain's Quarters at Spinnakers Vacation Cottages

Guest favourite

Home in Holmes Beach

4.98 out of 5 average rating, 45 reviews

D's Hideaway

Guest favourite

Home in Bradenton

5 out of 5 average rating, 25 reviews

On the Water. Private Boat Dock. * Heated Swim Spa

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 85 reviews

Manatee Harbour - Heated Pool - canal access

Guest favourite

Home in Anna Maria

4.95 out of 5 average rating, 59 reviews

Beach House w/Private Pool & Hot Tub by Bean Point

Weekly house rentals

Home in Holmes Beach

4.8 out of 5 average rating, 44 reviews

Anna Maria Oasis | large home 5 houses from beach

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 23 reviews

Shore Beats Work, Bean Point Beauty on Anna Maria

Home in Anna Maria

4.94 out of 5 average rating, 94 reviews

2nd House from the Beach with No Roads to Cross

Guest favourite

Home in Bradenton

4.84 out of 5 average rating, 43 reviews

The "Love shack" Bungalow

Guest favourite

Home in Holmes Beach

4.9 out of 5 average rating, 51 reviews

Tropical Paradise with Pool, Spa and Beach Access!

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 37 reviews

Couple’s Seatreat Summer Rate Specials

Home in Holmes Beach

4.84 out of 5 average rating, 37 reviews

Cozy beach house with pool - 1 block from beach!

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 6 reviews

Fins to the Right: On the Gulf of Mexico! Beach!

Private house rentals

Guest favourite

Home in Longboat Key

4.96 out of 5 average rating, 71 reviews

Beautiful Beach House

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 31 reviews

Pool, putting green, pickleball, tiki bar, hot tub

Guest favourite

Home in Bradenton

4.93 out of 5 average rating, 29 reviews

My Blissful Place by the Bay - Bring your boat!

Home in Holmes Beach

4.9 out of 5 average rating, 58 reviews

TOES IN THE SAND!

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 15 reviews

Villa Mar- 2BD Waterfront Home in Holmes Beach, FL

Guest favourite

Home in Bradenton Beach

4.89 out of 5 average rating, 64 reviews

Entire Duplex Golf Carts Heated Pool! Walk 2 beach

Guest favourite

Home in Bradenton

5 out of 5 average rating, 15 reviews

Canal front, dock, heated Pool, near AMI+IMG

Home in Holmes Beach

4.89 out of 5 average rating, 57 reviews

Sea Glass Cottage

Destinations to explore