Holiday rentals in Anna Maria

4.96 out of 5 average rating, 180 reviews

Be an 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.

Apartment in Holmes Beach

4.98 out of 5 average rating, 124 reviews

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

4.98 out of 5 average rating, 119 reviews

Apartment in Bradenton

KING Bed + AMI Beaches!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

5 out of 5 average rating, 19 reviews

Tiny home in Bradenton

Romantic Luxe Tiny Home+ Hot Tub

Escape to a tropical paradise in this brand new luxury tiny home, nestled among palm trees. Relax in the private hot tub. Just 6 miles to Anna Maria. Ideal for a romantic getaway or a peaceful retreat. We are located in a quiet neighborhood with a 10PM noise ordinance. If you want a quiet relaxing getaway, our tiny home is perfect for you. A car is recommended in this area as there is limited public transportation. The best rental car rates can be found at TPA/SRQ airport.

4.99 out of 5 average rating, 116 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!

Cottage in Bradenton Beach

4.99 out of 5 average rating, 176 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.98 out of 5 average rating, 106 reviews

Townhouse in Anna Maria

CHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B

Location! North end of Anna Maria Island . This charming two story duplex- each unit has two bedrooms , one bathroom. Rent one unit or both. Perfect for a group of extended family and friends. Steps to the Bean Point Beach . Includes beach chairs, umbrellas and all you need for a perfect day at the beach! Heated pool , private seating, grilling areas, bicycles and much more available. MAX Occupancy 4 people including children of any age.

4.97 out of 5 average rating, 142 reviews

Guest suite in Bradenton

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

4.94 out of 5 average rating, 106 reviews

The Peachy Beach House, steps to the gulf

Hurricane season cancellation possible. Saturday-Saturday for check-in and out. Two bedroom, 2 full bathroom, new heated private pool Steps from semi-private gulf beach, this 3 story on a quiet street in N. HB Well-stocked kitchen, 2 TVs, large master which is more like resort suite with new tempurpedic king bed Gulf views from bedrooms. You’ll find: crib, high chair, beach chairs, wagon, canopy, beach toys and towels!

Guest house in Anna Maria

5 out of 5 average rating, 31 reviews

The Boathouse

Would you like to feel like you are sleeping in a tree house with all the luxuries and comfort of a high end hotel? Then welcome to our brand new guest house, which accommodates a maximum of two guests and is a completely private tropical oasis. Standing on the edge of Lake LaVista, surrounded by tropical palms where you have use of the private and beautiful pool which we heat during the winter months.

5 out of 5 average rating, 68 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

Superhost

Apartment in Holmes Beach

4.93 out of 5 average rating, 112 reviews

1/1 STEPS to Beach w/ Heated POOL - Sleeps 4

Spacious and remodeled 1-bedroom condo that sleeps 4 located just STEPS away from the beach. Condo features a large heated swimming pool, private beach access, eat-in kitchen - fully stocked with amenities including coffee maker, WiFi, Smart Tv's, beach accessories, fishing poles, paddle boards, games, & much more! Early Check-in / Late Check-out available upon request.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Anna Maria holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Anna Maria

4.91 out of 5 average rating, 46 reviews

Backyard Bliss Anna Maria Island

NancyRating, 5 stars2 weeks ago

We thoroughly enjoyed Backyard Bliss. It was tucked away in a little cul-de-sac with a very short walk to the beautiful beach. The house had everything we needed for inside as well as everything needed for a day at the beach. And the pool was wonderful!!

Flat in Anna Maria

4.97 out of 5 average rating, 36 reviews

Quaint 2 BR/1B, a few houses from the beach

NicoleRating, 5 stars11 months ago

Gina's place was perfect for our family of 4 visiting AMI. The location is amazing-several houses from the beach and close to both the busier Holmes Beach city area and Bean Point restaurants, shops, piers. It is able to accommodate a (electric) golf cart, plus car parking. The 2nd story unit is the upper story to the owner's home but has a private entrance and feels very separate. The laundry is in separate "shed" area that is shared, but more than adequate for a vacation, which is where the outdoor shower area is. It was nicer than expected based on photos - the living room area is a separate room, with comfortable furniture, off the kitchen providing great relaxing space for the whole family. The kitchen is nice and well stocked with dishes, etc. The bedrooms were comfortable, and the furniture, linens and towels were in good or better condition. Gina provided us with a wagon, beach chairs, a beach umbrella and beach toys. Everything was in good condition, clean and inviting.

5 out of 5 average rating, 8 reviews

Bayfront Beach access with Heated Pool!

DarciRating, 5 stars1 month ago

3 couples Spent 9 days of pure relaxation in this charming beach home with the best homey beach vibes and decor. The home is bright and Sunny with a private backyard that looks straight through the garage port to the beautiful ocean waters right from the pool when the garage door is open. The whole front of the house has a beautiful view. Great for sitting out on the deck and people watching . We could even see dolphins out there swimming from the house. All kinds of thoughtful personal touches and amenities were taken into consideration when thinking of guests and their vacation needs. We wouldn’t hesitate to rent this house again in the future. We felt right at home.

4.8 out of 5 average rating, 5 reviews

Gulf Front Villa with View! - Whispering Waves

SophieRating, 5 stars18 months ago

Great place, good value for your money

5 out of 5 average rating, 14 reviews

Shore's Nice - Private home across the street

JacquelineRating, 5 stars2 weeks ago

Location was perfect! We loved being steps away from the beach! The house was clean, nicely decorated and well equipped. It felt like a second home! Would definitely stay here again! We highly recommend this home!

Townhouse in Holmes Beach

5 out of 5 average rating, 16 reviews

Townhouse 200 Steps to the Beach

MrunalRating, 5 stars2 weeks ago

Great place, great location and good amenities. We had fun.

Superhost