We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

House holiday rentals in Anna Maria Island

Find and book unique houses on Airbnb

Top-rated house rentals in Anna Maria Island

Guests agree: these houses are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Home in Holmes Beach

4.88 out of 5 average rating, 104 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 Holmes Beach

4.95 out of 5 average rating, 173 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

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

4.95 out of 5 average rating, 144 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

4.9 out of 5 average rating, 106 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 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, 48 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 Beach

4.82 out of 5 average rating, 133 reviews

50 Steps to Beach Villa Hot Tub 1bd modern cottage

Luxury Beach Cottage w/ HOT TUB, Fire Pit & BBQ. 1 bed/2bath sleeps 4 This is your chance to enjoy a unique getaway on the nicest beach! Stay in our newly remodeled beach cottage. White sandy beach & turquoise water is literally 50 ft from the door. Everything you need for a delightful & relaxing day at the beach is included. Chairs, beach towels, umbrella, snorkels, masks & a cooler. Enjoy the convenience of this premium location across Gulf blvd to Beach.

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 9 reviews

Ocean Air Oasis-New Centrally Located AMI Luxury

Immerse yourself in coastal luxury at this exceptional 3-bedroom, 2.5-bathroom custom home, where opulent high-end finishes and stunning pecky cypress floors adorn every nook. Revel in the impeccable features, including Sub-Zero and Wolf appliances, marble countertops, Shaw’s sinks, and exquisite custom woodworking, all bathed in abundant natural light. This delightful space offers panoramic views of the lavish backyard, complete with a heated pool and spa.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Bungalows

Intimate homes, inviting architecture

Cottages

Quaint homes, peaceful surroundings

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

4.94 out of 5 average rating, 89 reviews

Breezy Harbor AMI pool retreat near the Beach

Guest favourite

Home in Holmes Beach

4.93 out of 5 average rating, 41 reviews

Backyard Bliss Anna Maria Island

Guest favourite

Home in Holmes Beach

4.98 out of 5 average rating, 45 reviews

D's Hideaway

Home in Indian Rocks Beach

4.84 out of 5 average rating, 326 reviews

Stunning views! Spot dolphins from the pool!

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 21 reviews

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

Guest favourite

Home in Anna Maria

5 out of 5 average rating, 85 reviews

Manatee Harbour - Heated Pool - canal access

Guest favourite

Home in Bradenton

5 out of 5 average rating, 16 reviews

Birds and Sunsets

Guest favourite

Home in Holmes Beach

4.88 out of 5 average rating, 17 reviews

Seashell Shack! Ready to rent! Holiday sale!

Weekly house rentals

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

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 Bradenton

4.85 out of 5 average rating, 46 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!

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 Anna Maria

5 out of 5 average rating, 22 reviews

Anna Maria Beach House

Guest favourite

Home in Bradenton

5 out of 5 average rating, 27 reviews

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

Guest favourite

Home in Bradenton

4.97 out of 5 average rating, 39 reviews

Near AMI-Fire Pit-Hot Tub-Christmas tree-Game room

Private house rentals

Home in Anna Maria

4.94 out of 5 average rating, 94 reviews

2nd House from the Beach with No Roads to Cross

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

Guest favourite

Home in Bradenton

5 out of 5 average rating, 16 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

Home in Bradenton

5 out of 5 average rating, 3 reviews

New! Amazing Heated Pool w/ Bay Views! 7 min to Be

Home in Holmes Beach

5 out of 5 average rating, 3 reviews

New Listing! Sailfish Villa, Steps from the Sand!

Destinations to explore