50 Best Anna Maria Island Vacation rentals on Holiday Lettings - Beach rentals

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Anna Maria Island

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842 Vacation rentals

(5) Excellent 

15

Anna Maria Island Vacation cottage rental

Florida / Anna Maria Island

1 3 4 nights min

  • 1 bedroom
  • Sleeps 3
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Shell Cottage is situated just 200ft away from the beautiful white sandy beach of Anna Maria which is 7 miles long. Set in a quiet leafy lane Shell shares our heated pool with our other 2 cottages and can be rented together or separately. Shell Cottage has a small sofa- …see more

from $135 / night

$945 - $1085 / week

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from $135 / night

(1) Good 

15

Vacation home in Anna Maria Island

Florida / Anna Maria Island

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
BEACHCOMBER, just 200ft from 7 miles of white sandy beach, is a beautifully furnished cottage with 2 bedrooms, 1 double and 1 twin. The master bedroom has an en-suite bathroom. There is also a 2nd bathroom with shower, WC and basin only. A large open plan living room …see more

from $145 / night

$1015 - $1225 / week

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from $145 / night

(1) Excellent 

11

Anna Maria Island Vacation home rental

Florida / Anna Maria Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
The Beach House is situated on one of the quietest areas of the beautiful white sandy beach, that stretches from one end of the island to the other. A nature lovers paradise where you can sit on the balcony with a glass of chilled wine and watch the dolphins play in the …see more

from $285 / night

$1995 - $2660 / week

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from $285 / night

(35) Excellent 

41

Townhouse rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Our modern, luxury townhouse enjoys a fantastic location on Bradenton Beach; within easy walking to a number of shops, restaurants and a host of activities. Packed with all the mod cons (including free WiFi) you could possibly need for a wonderfully relaxing holiday, ou …see more

from $172 / night

$1200 - $1800 / week

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from $172 / night

11

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 60 nights min

  • 2 bedrooms
  • Sleeps 6
  • 60 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful island condo is newly refurbished and redecorated for a perfect get-away. This quiet, 55+ community is a paradise. Situated in Anna Maria Island, Florida, the island has quiet, old-Florida charm with numerous restaurants, shops, and conveniences. A fre …see more

from $94 / night

$654 / week

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avg. 1 hour 12 minutes

from $94 / night

16

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
At the entrance to Anna Maria Island, on Perico Island overlooking Anna Maria Sound is the gorgeous 220-acre island oasis and Florida’s newest private waterfront resort. Within this gated community is our fully furnished southern coastal coach home, which features 3 be …see more

from $167 / night

$1167 / week

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avg. 2 hours 20 minutes

from $167 / night

(1) Excellent 

8

Anna Maria Island Vacation apartment rental

Florida / Anna Maria Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our apartment is located in close proximity to one of the most beautiful beaches of Florida. The apartment has a master bedroom with king size bed, TV, bathroom with shower or shower basin and toilet and a sep. Guest room with adjoining bath towels and linens are provid …see more

from $108 / night

$751 - $1200 / week

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from $108 / night

(1) Very Good 

33

Vacation home rental

Anna Maria Island / Bradenton Beach

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful barrier island. Your accommodations are less than 1/2 bl …see more

from $350 / night

$1800 - $3900 / week

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from $350 / night

(13) Excellent 

Certificate of Excellence

44

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the …see more

Certificate of Excellence

from $225 / night

$1400 - $3500 / week

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avg. 1 hour 35 minutes

from $225 / night

(20) Very Good 

45

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of th …see more

from $290 / night

$1775 - $4750 / week

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avg. 2 hours 30 minutes

from $290 / night

(2) Excellent 

12

Holmes Beach Vacation villa rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
This lovely property features a tropical setting surrounding a heated swimming pool. The six unit complex is located one block from the beach. Great for family reunions or wedding parties. This unit is a two bedroom one bath full size apartment. King bed in bedroom and …see more

from $140 / night

$835 - $1210 / week

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avg. 1 hour 32 minutes

from $140 / night

(1) Excellent 

39

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. Th …see more

from $243 / night

$1700 - $3200 / week

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from $243 / night

10

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
2206 Ave. B - Private Bungalow 2 Bedroom / 1 Bath, maximum occupancy of 4 people and one small dog. Quaint Island bungalow with an enclosed garage. In a friendly neighborhood in Bradenton Beach where the water is sparkling blue and the beaches are beautiful. Enjoy bi …see more

from $100 / night

$700 - $880 / week

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from $100 / night

(27) Excellent 

52

Vacation home rental

Anna Maria Island / Holmes Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood …see more

from $249 / night

$1494 / week

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avg. 1 hour 47 minutes

from $249 / night

(4) Excellent 

39

Vacation home with swimming pool in Anna Maria

Anna Maria Island / Anna Maria

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Mar …see more

from $314 / night

$2199 / week

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avg. 1 hour 16 minutes

from $314 / night

24

Cottage rental in Anna Maria

Anna Maria Island / Anna Maria

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
4 Bedroom, 2 Bath (sleeps 8) - "Blue Heron Beach House" - 117 Peppertree Lane in Anna Maria.  Welcome to “Blue Heron Beach House”! This adorable Anna Maria beach cottage rental is so close to the Gulf of Mexico you can smell the salt air! Enjoy sugar sand beaches and c …see more

from $265 / night

$1855 - $4025 / week

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avg. 3 hours 5 minutes

from $265 / night

22

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a me …see more

from $175 / night

$2000 - $3600 / week

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avg. 2 hours 42 minutes

from $175 / night

69

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
FAMILY/CHILD FRIEDLY CONDOMINIUM. The Anna Maria Island Beach Palms 7A is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that lea …see more

from $107 / night

$749 / week

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from $107 / night

(4) Excellent 

16

Vacation cottage in Anna Maria

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine …see more

from $169 / night

$1500 / week

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avg. 1 hour 41 minutes

from $169 / night

(3) Very Good 

21

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning
Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room …see more

from $200 / night

$1090 - $1750 / week

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avg. 1 hour 32 minutes

from $200 / night

(8) Excellent 

25

Vacation home in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island …see more

from $259 / night

$1813 / week

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avg. 1 hour 42 minutes

from $259 / night

(5) Very Good 

15

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitch …see more

from $150 / night

$825 - $1350 / week

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avg. 1 hour 32 minutes

from $150 / night

(6) Excellent 

23

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make t …see more

from $269 / night

$1883 / week

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avg. 1 hour 32 minutes

from $269 / night

(3) Excellent 

25

Vacation townhouse in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
*NOTE: If you cannot find availability for this unit, please contact us, there is an additional unit. Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along …see more

from $99 / night

$693 / week

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avg. 1 hour 6 minutes

from $99 / night

30

Vacation home rental

Anna Maria Island / Anna Maria

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom boast …see more

from $325 / night

$1400 - $2310 / week

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from $325 / night

24

Home rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Suitable for children age 5+
This rental home on Anna Maria Island sleeps up to 10 and comes fully equipped. This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful …see more

from $280 / night

$1960 - $4725 / week

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avg. 3 hours 5 minutes

from $280 / night

(5) Very Good 

30

Vacation condo in Anna Maria Island

Florida / Anna Maria Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Your Anna Maria Island Paradise!! Vacation on a beautiful island that is surrounded by the warm Florida sun. This paradise getaway, known as Anna Maria Island, is seven miles of warm-white sandy beaches on the Gulf of Mexico where you can swim, walk, relax, …see more

from $115 / night

$800 / week

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avg. 22 minutes

from $115 / night

(20) Excellent 

Certificate of Excellence

32

Vacation home accommodation

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
**DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GAR …see more

Certificate of Excellence

from $215 / night

$1500 - $2250 / week

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from $215 / night

(2) Excellent 

69

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
FAMILY/CHILD FRIEDLY CONDOMINIUM. Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island Beach Palms 5B is completely surrounded by water and has just been completely updated with a new s …see more

from $115 / night

$805 / week

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from $115 / night

10

Bradenton Beach Vacation apartment rental

Anna Maria Island / Bradenton Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
2307 AVENUE C - Duplex 3 Bedroom / 2 Bath with pool, maximum occupancy of 6 people. Come and swim with the turtles!~ Adorable and totally renovated 3 bedroom and 2 bath duplex on the second floor, one street back from Gulf Drive on the beach. The first floor is storage …see more

from $189 / night

$1320 - $1815 / week

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from $189 / night

(1) Excellent 

21

Vacation home in Anna Maria

Anna Maria Island / Anna Maria

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Ame …see more

from $300 / night

$2100 - $3335 / week

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from $300 / night

(12) Excellent 

23

Apartment rental in Bradenton Beach

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Overlooking the Gulf of Mexico Beach, these 1250 square feet each two bedroom beach townhouses (complex of 4 apartments) arranged on two elevated levels offer beautiful views of Anna Maria island sound. A nice yard with a access to a barbecue area and a six persons tub …see more

from $220 / night

$1800 - $2450 / week

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avg. 1 hour 5 minutes

from $220 / night

51

Bradenton Beach Vacation apartment accommodation

Anna Maria Island / Bradenton Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
FAMILY/CHILD FRIEDLY CONDOMINIUM. The Beach Palms is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on historic Bridge St. that leads right out onto the …see more

from $115 / night

$805 / week

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from $115 / night

(2) Very Good 

14

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitch …see more

from $150 / night

$825 - $1350 / week

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avg. 1 hour 32 minutes

from $150 / night

(5) Very Good 

17

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up …see more

from $200 / night

$1095 - $1695 / week

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avg. 1 hour 32 minutes

from $200 / night

31

Vacation villa in Anna Maria

Anna Maria Island / Anna Maria

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the h …see more

from $145 / night

$845 - $1600 / week

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from $145 / night

33

Vacation home with shared pool in Anna Maria

Anna Maria Island / Anna Maria

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all …see more

from $600 / night

$3251 - $5250 / week

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from $600 / night

(9) Excellent 

21

Vacation apartment in Bradenton Beach

Anna Maria Island / Bradenton Beach

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, …see more

from $250 / night

$1250 - $1950 / week

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from $250 / night

(4) Excellent 

21

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge poo …see more

from $100 / night

$650 - $1400 / week

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from $100 / night

(5) Excellent 

24

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary
One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps …see more

from $165 / night

$825 - $1390 / week

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avg. 1 hour 32 minutes

from $165 / night