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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

4.99 out of 5 average rating, 155 reviews

Captain's Quarters at Spinnakers Vacation Cottages

My place is close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love my place because of the high ceilings, the location, and the ambiance. It is located in the lush tropical paradise of Spinnakers Vacation Cottages. With a large living room, dining area and large master suite, it is perfect for couples, families (with kids), and furry friends (dogs, with a small pet fee). Spa maintains same temperature as pool. Captains Quarters also has Private patio!

Guest favourite

Home in Bradenton

4.93 out of 5 average rating, 135 reviews

Endless Outdoor FUN! Pool/Spa/Golf/Games/Near IMG.

Make memories at this unique, FUN, family friendly place. Let The Sunshine House fill you with joy! This happy 3 bed/2 bath home will have you and your guests smiling from ear to ear with the beautiful decor. Fully stocked for the beach (only 6 MILES away) or stay &enjoy the amenity-rich backyard with <b>turf, putting green, heated pool, hot tub, grill, stone fire pit, yard games& lots of fun photo ops!</b> At night this place is even more jaw dropping w/colorful lights. Leaving will be 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 Anna Maria

4.98 out of 5 average rating, 44 reviews

Ready to Host! Anna Maria Chateau. Private Pool!

Anna Maria Chateau is a well appointed coastal home located just a quick walk from the beach. Walk to the local pier or restaurants and shops. The heated pool is gorgeous and lined with large palm trees to provide privacy. Plenty of outdoor entertainment games, bar and large screen TV. This home offers 3 bedrooms and 2 full bathrooms. The living area provides plenty of Florida sunshine and a large outdoor covered lanai overlooking the pool. Sleeping :2 king bedrooms and 2 sets of twin bunks.

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 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 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 Anna Maria

4.99 out of 5 average rating, 102 reviews

1 block to Beach on Pine Ave! Private Pool Oasis

Sat-Sat rentals, usually... Our 3 bedroom, 2 bath townhouse, with a private heated-pool oasis, is on Pine Ave in the heart of Anna Maria - 1 ½ blocks from the best white sand beach on the island - 3 blocks in the other direction to the bay - from sunrise at the City Pier to Sunset on the Gulf of Mexico. Walk or ride a bike to all the quaint stores, shopping and restaurants (plus the local doughnut, taco shop and Northshore Cafe next door) without ever getting in your car!

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

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Bungalows

Intimate homes, inviting architecture

Popular amenities for Anna Maria Island house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Bradenton Beach

4.94 out of 5 average rating, 33 reviews

Beach Bliss! Holiday specials! Walk to beach!

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 Holmes Beach

5 out of 5 average rating, 13 reviews

6 Bed/5.5 Bath Heated Pool -1 Minute Walk to Beach

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 14 reviews

Castaway Cottage

Guest favourite

Home in Holmes Beach

4.98 out of 5 average rating, 45 reviews

D's Hideaway

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 39 reviews

Perfect Hideaway- Post Storms Better Than Ever!

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 21 reviews

4 Bed / 4 Bath with Stunning Views of Bimini Bay !

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

5 out of 5 average rating, 37 reviews

Couple’s Seatreat Summer Rate Specials

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 22 reviews

Anna Maria Beach House

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 5 reviews

CabAnna Maria Beach Block 4 Bedroom 4.5 Bath

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 36 reviews

Near AMI-Fire Pit-Hot Tub-Game Room-Putting Green

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 Holmes Beach

4.9 out of 5 average rating, 51 reviews

Tropical Paradise with Pool, Spa and Beach Access!

Home in Holmes Beach

4.9 out of 5 average rating, 58 reviews

TOES IN THE SAND!

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 34 reviews

My Summer Breeze by the Bay.

Guest favourite

Home in Holmes Beach

5 out of 5 average rating, 15 reviews

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

Home in Bradenton Beach

5 out of 5 average rating, 10 reviews

Tropical AMI Retreat w/golf cart and POOL

Home in Holmes Beach

4.84 out of 5 average rating, 37 reviews

Cozy beach house with pool - 1 block from beach!

Home in Holmes Beach

4.89 out of 5 average rating, 57 reviews

Sea Glass Cottage

Destinations to explore