Anna Maria Island Holiday Rentals

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Holiday Rentals in Anna Maria Island

Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (155)
"Had an amazing stay. Will definitely be back!"
The price is NZ$1,400
per night
2 Jun - 3 Jun
Anna Maria Beach Resort
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (188)
"Great property, it’s close to the beach, restaurants, checking in and out very easy (all done via text and phone). The beach across the street is beautiful. Definitely coming back."
The price is NZ$745
per night
10 Jun - 11 Jun
Pelican Post at Anna Maria Island Inn
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Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (380)
"Amazing property and super friendly staff. We had the best time and our room was perfect. Full kitchen with everything we needed to make any meal. Washer/dryer that we could use plus so many little extras in the supply house we could use if needed! Pool was clean and beautiful. Beach was super close, just about a minutes walk away. Will definitely be returning in the future! "
Queen's Gate Resort
Tradewinds Beach Resort
2.5 star property
9.2 out of 10, Wonderful, (353)
"Friendly staff. Diane was very helpful."
Tradewinds Beach Resort
Anna Maria Sunsets - studio
9.4 out of 10, Exceptional, (185)
"Nice room, a little small but adequate, although an outside area for sitting (private) would have been nice. Excellent location across a busy street from a beautiful beach with a shady gazebo to sit in and next to a jet ski rental! Anna Maria Free Shuttle takes you up and down the island and runs every 20 minutes, with a stop very close by. Walking distance to the "Bridge Street" shopping and dining block!"
The price is NZ$463
per night
30 Jun - 1 Jul
Anna Maria Sunsets - studio
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (347)
"Quick little walk to beach. Great beach chairs. Best location on the beach. They were easily and quick to get in touch with for questions and the location was perfect. "
The price is NZ$672
per night
2 Jun - 3 Jun
Haley's at The Anna Maria Island Inn
The Pink House Unit B: A Cozy Retreat Steps from the Beach
9.8 out of 10, Exceptional, (65)
"The Pink House Unit B was one of the best units I have stayed using VRBO for years now. The pictures do it perfect justice. It’s a nice quaint space with a 1 min walk to beach. The unit is literally across the street from the beach which was quiet, not crowded at all. The only tiny drawback was the bathroom. The shower and toilet do need updates but don’t let that detour you one bit. Great place and location! I would rent again for sure!!!"
The Pink House Unit B: A Cozy Retreat Steps from the Beach
The Sailor Park
3.0 star property
3.2 out of 10, (15)
"This was a very welcome get away. Absolutely beautiful views. The owner is great. I definitely will come back. "
The price is NZ$249
per night
31 May - 1 Jun
The Sailor Park
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
9.8 out of 10, Exceptional, (258)
"Absolutely beautiful property & location was amazing!!! We had an absolutely wonderful time!! The house has a wonderful lanai and pool area that accommodates many people …. This home has a lot of steps that was the only downfall so if you have somebody in your party, that can’t handle steps. This wouldn’t be a good location for them but other than that everything was great."
Heated pool with private outdoor "kitchenette", hot tub, and fire pit!!!!
Completely remodeled beach front condo with full ocean views, steps to the water
9.8 out of 10, Exceptional, (190)
"This is a lovely modern condo with excellent furnishings. This was an effortless vacation."
The price is NZ$891
per night
11 Jun - 12 Jun
Completely remodeled beach front condo with full ocean views, steps to the water
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, (159)
"This property was true to pictures, very beautiful private beach, and the surrounding areas were very well maintained. Our host was exceptional, and our gorgeous rental was spotless.I would absolutely recommend this rental!!"
The price is NZ$1,337
per night
2 Jun - 3 Jun
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
9.8 out of 10, Exceptional, (156)
"PROPERTY WAS IN A PERFECT LOCATION ON THE ISLAND Had a fantastic week."
COZY APT IN QUAINT QUADRAPLEX HOME. STEPS TO BEACH! 1 BR/1BA. SLEEPS 2. POOL
Vibrant Island Home w/ Pool, 1 Block to Beach
9.6 out of 10, Exceptional, (28)
"Home close to beach and restaurants."
Vibrant Island Home w/ Pool, 1 Block to Beach
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
9.8 out of 10, Exceptional, (58)
"We had a wonderful week at Villa By The Sea #3! You can walk to the beach and lots ofshops and restaurants. Condo is small but nice for a couple."
Villa by the Sea #3; Heated Pool, Walk to Beach & Shops- Perfect Location!
Charming cottage in quiet area, close to beach & bay.
9.8 out of 10, Exceptional, (234)
"This charming 2 bed, 1 bath cottage is in the perfect location. It is in walking distance to coffee shops, breakfast spots and dinner restaurants. Close to the beach one direction and city pier the other. It is well stocked with all you would need and exceptionally clean. The screened porch in back with solar lighting in the back yard is ideal for your evening glass of wine! Definitely recommend!"
Charming cottage in quiet area, close to beach & bay.
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
10.0 out of 10, Exceptional, (97)
"This was our 2nd year staying at Rum Cove and we would definitely book this house again. The property managers were very responsive to one minor issue that we had on check in. The house is in walking distance to the beach, the pier and many restaurants and shops."
DISCOUNT OFFER! Rum Cove-Magical Tropical Oasis: Pool/Hot Tub, Golf Cart, Kayak
Anna Maria Beach Condo 1/1
9.8 out of 10, Exceptional, (178)
"Beautiful area, condo was very clean and beautifully decorated. Plenty of room for 2 people (my sister and me..) Huge, comfortable king sized bed. Nice roomy closets. Excellent bathroom with privacy door between double sink vanity area and shower /toilet. Fully equipped cheery kitchen. Private, roomy screened in balcony . And the beach was magnificent......"
The price is NZ$545
per night
14 Jun - 15 Jun
Anna Maria Beach Condo 1/1
Anna Maria Sunsets - studio
9.2 out of 10, Wonderful, (174)
"I had no idea that a unit on the second floor was actually on the third floor above the garage and we had to take the steps because the elevator was broken. It was very hard to find and has a weird one way driveway that you have to see to believe. Once we finally got into the unit it was fine. Thought I might have a heart attack lugging suitcase up but I lived. My husband’s recent knee replacement didn’t like the two flights of stairs either. But would it kill you to include a coffee maker and a...
The price is NZ$434
per night
10 Jun - 11 Jun
Anna Maria Sunsets - studio
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
9.8 out of 10, Exceptional, (132)
"Loved the convenience of the location. The manager was very helpful when needed"
The price is NZ$661
per night
3 Jun - 4 Jun
Gulf & Sunset Views!!! 1BR Apt. B is a Centrally Located, walk to all location
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Anna Maria Island you may be interested in

Silver Surf Gulf Beach Resort
3.0 star property
9.4 out of 10, Exceptional, (1002)
"Family vacation. Loved having direct beach access, with chairs and an umbrella set up for us! Relaxing in the pool after the beach and taking trolley rides around town! "
The price is NZ$436
per night
16 Jun - 17 Jun
Silver Surf Gulf Beach Resort
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Bali Hai Beachfront Resort and Spa
3.5 star property
8.6 out of 10, Excellent, (449)
"The staff was amazing! Mike the bartender is great! The manager was so kind. Front desk staff super helpful. Great place. We loved it so much, we WILL be coming back!"
The price is NZ$743
per night
9 Jun - 10 Jun
Bali Hai Beachfront Resort and Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Anna Maria Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Anna Maria Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Anna Maria Island. Seeing all the best attractions is bound to make you fall in love with Anna Maria Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Anna Maria Island short-term rentals, that won’t be hard to do.

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