50 Best Holmes Beach Vacation rentals on Holiday Lettings - House rentals

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464 Vacation rentals

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

(2) 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

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Swimming pool
Very spacious two bedroom Condo with a large living room. Flat Screen TV, fully equipped kitchen with all the appliances. Not far from the beach, and short distance to area shopping. Unit has heated pool, and a relaxing Pool deck area. Main bedroom has a King size bed w …see more

from $125 / night

$700 - $1200 / week

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from $125 / 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 $166 / night

$825 - $1390 / week

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avg. 1 hour 5 minutes

from $166 / night

(2) Excellent 

31

Vacation cottage with swimming pool in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fir …see more

from $200 / night

$1125 - $1200 / week

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from $200 / night

21

Vacation townhouse in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Swimming pool
Newly Remodeled & Professionally Decorated Large Townhome in Desirable North Beach Village, one Block from beautiful White Sand Beaches. Brand new Upscale Furnishings in all Rooms. Big Flat Screen Smart TV's in all rooms with Premium HD Cable & WiFi powerful enough to …see more

from $250 / night

$1600 - $2400 / week

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from $250 / night

(4) Very Good 

24

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Horizon West 112 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. Beach Bound.....This is your place!~ 2 bedroom 2 bath condo 1 very short block to beach. Beautifully decorated with comfortable furniture. Everything you need for a relaxing vacation. Pet fr …see more

from $115 / night

$730 - $1155 / week

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from $115 / night

(26) 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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Responds fast!
avg. 1 hour 49 minutes

from $249 / night

(1) Very Good 

11

Vacation apartment rental

Anna Maria Island / Holmes Beach

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.16 mi
  • Swimming pool
Gorgeous Efficiency and steps to white sandy beaches from this 1 bedroom, 1 bath elevated vacation rental, one story up overlooking pool area. Stairs go up to small deck in front of the efficiency. With 3 x 8 open deck to enjoy the sunsets, or overlooking pool. Feel th …see more

from $125 / night

$700 / week

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from $125 / night

(18) Excellent 

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

from $215 / night

$1500 - $2250 / week

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from $215 / night

103

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Pet friendly
Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily wi …see more

from $375 / night

$2625 - $4620 / week

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Responds fast!
avg. 2 hours 36 minutes

from $375 / night

31

Vacation apartment accommodation

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
Sandy Point 114 - Condo 2 Bedroom/ 3 Bath, maximum occupancy of 6 people. This 2 bedroom , 3 bath townhouse condo features 2 living floors and 3 verandas above an enclosed over-sized garage and located in the Cove at Sandy Pointe on beautiful Anna Maria Island! Surroun …see more

from $122 / night

$850 - $1760 / week

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from $122 / night

(2) Very Good 

37

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

4 14 7 nights min

  • 4 bedrooms
  • Sleeps 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Anna Maria Island offers a family oriented vacation destination, laid back feel ...very relaxing. The island's beauty, world famous white beaches and friendly atmosphere will make you want to come back. The four bedroom home with a Golf Cart to bop around the island. Th …see more

from $308 / night

$2150 - $5000 / week

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from $308 / night

(1) 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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Responds fast!
avg. 42 minutes

from $200 / night

(8) Excellent 

31

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This well-furnished two bedroom condo is next to a quiet nature preserve and has a fine view of the bay separating Anna Maria Island from Florida's mainland as well as the Sandy Pointe heated swimming pool. The beach is just 3 small blocks away with its bright white san …see more

from $125 / night

$720 / week

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from $125 / night

(2) Excellent 

20

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Ask about children
Totally furnished apartment close to the beach. Spend quality time in a nice neighborhood. Enjoy activities such as playing tennis, kayaking, water skiing, fishing, painting, swimming, walking your dog and meeting new people at the dog park , the library or the Communit …see more

from $115 / night

$800 - $901 / week

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from $115 / night

(12) Excellent 

35

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
**Due to a house being built in frount of our building, we don't know how our views of the Mexican Gulf will be affected. We cannot guarantee that you will have the views depicted in our pictures.** 5 reasons why you will love our condos as much as we do: …see more

from $143 / night

$999 - $2150 / week

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Responds fast!
avg. 11 minutes

from $143 / night

(2) Excellent 

19

Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Lovely Bayside Condo recently remodeled, 2 Bedroom, 2 Bathroom, fully air conditioned, screened lanai, heated pool and covered parking. Easy access to: retail shops, grocery store and restaurants. 200 hundred yards to Free Island Trolley. Five minute walk to white sand …see more

from $128 / night

$896 / week

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from $128 / night

(1) Excellent 

18

Holmes Beach Vacation condo rental

Anna Maria Island / Holmes Beach

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This two bedroom, two-bath condo has been tastefully renovated and refurbished. The kitchen has new appliances and granite countertops. All the new furnishings make this a very comfortable home away from home. It has a private screened balcony off the living room and b …see more

from $130 / night

$901 / week

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from $130 / night

(11) Excellent 

28

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a …see more

from $136 / night

$950 - $1600 / week

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from $136 / night

(1) Very Good 

17

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel applia …see more

from $154 / night

$853 - $2375 / week

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Responds fast!
avg. 2 hours 36 minutes

from $154 / night

16

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning
2 Bedroom, 1 Bath (sleeps 4-6) - "Playa Casanas South" - 3222 Gulf Drive unit A in Holmes Beach. “Playa Casanas South” is a wonderful vacation rental home directly on the sparkling white quartz sands of the Gulf of Mexico. Sleeping up to six guests comfortably in t …see more

from $170 / night

$1190 - $2065 / week

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Responds fast!
avg. 2 hours 38 minutes

from $170 / night

(4) Very Good 

27

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated 3 blocks from the beach and 2 blocks from the bay with a secluded yard surrounded by mangroves, this two-story pool home includes 3 bedrooms on the first floor and a regal master suite on the second floor. Comes equipped with Wifi, cable TV in all 4 bedrooms, w …see more

from $300 / night

$1760 - $1865 / week

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from $300 / night

(23) Very Good 

17

Vacation home rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. We …see more

from $125 / night

$850 - $1300 / week

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Responds fast!
avg. 1 hour 1 minutes

from $125 / night

14

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel applia …see more

from $150 / night

$852 - $2375 / week

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Responds fast!
avg. 2 hours 36 minutes

from $150 / night

(1) Excellent 

16

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has 2 full size beds. Its just steps t …see more

from $130 / night

$720 - $995 / week

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Responds fast!
avg. 1 hour 5 minutes

from $130 / night

23

Vacation villa rental

Anna Maria Island / Holmes Beach

1 8 Min stay varies

  • 1 bedroom
  • Sleeps 8
  • 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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Responds fast!
avg. 1 hour 5 minutes

from $200 / night

(4) Very Good 

22

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 - $1230 / week

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Responds fast!
avg. 1 hour 5 minutes

from $150 / night

(1) 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 5 minutes

from $140 / night

(2) Excellent 

22

Holmes Beach Vacation cottage rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.02 mi
  • Swimming pool
ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your fa …see more

from $199 / night

$901 - $1600 / week

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Responds fast!
avg. 2 hours 4 minutes

from $199 / night

(5) Very Good 

17

Vacation home rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
This charming 2 Bedroom 2 Bath is the fourth house from the gorgeous white sand beach on the Gulf of Mexico. Remodeled and updated, this fully furnished home features 1450 sq ft, plus garage and patio. Amenities include living room plus family room with TVs in both, fu …see more

from $136 / night

$950 / week

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from $136 / night

23

Vacation villa in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Lush tropical landscaped setting. Beautifully maintained two bedroom vacation rental on gorgeous Anna Maria Island. Secluded beaches, shopping, restaurants, golf, fishing and relaxation. Apartment includes full kitchen, 50' flat screen TV in living room, flat screen TV …see more

from $159 / night

$950 / week

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from $159 / night

(3) Good 

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Car not necessary
  • Air conditioning
Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has a king size bed. Its just step …see more

from $130 / night

$720 - $995 / week

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Responds fast!
avg. 1 hour 5 minutes

from $130 / night

(5) Excellent 

27

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Child friendly
This property is available for rentals 7 nights or more. 99 steps from the beach! Elegantly furnished two bedroom and two bath condo with brand new Tommy Bahama style furnishings. Sit by the heated pool after a stroll on the white, sandy beach of Holmes Beach just acr …see more

from $193 / night

$1200 - $1780 / week

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from $193 / night

(1) Excellent 

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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Responds fast!
avg. 1 hour 5 minutes

from $150 / night

(2) Very Good 

15

Vacation home rental

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Perhaps Shady Palms will become "your place on the beach." Walk into a charming, Old Florida style beach cottage with a view of the beautiful Gulf of Mexico from every room in the house. Continue through the back door, and into the yard and you are one step from the wi …see more

from $286 / night

$2000 - $2400 / week

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from $286 / night

21

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 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 $200 / night

$1090 - $1695 / week

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Responds fast!
avg. 42 minutes

from $200 / night

13

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fun and beachy lower duplex with pool on Anna Maria island. Only a block and a half from the beach. Wash the sand off fro the beach with the outdoor shower and foot wash. Play or relax by the pool. Outdoor furniture is perfect for eating or entertaining outside. Lo …see more

from $131 / night

$917 / week

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Responds fast!
avg. 13 minutes

from $131 / night

(1) Excellent 

30

Holmes Beach Vacation apartment rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Make your stay in Florida fun and easy! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up and down the coast. The condo is on the top floor (6th) of the building and is completely furnished with a dining table that seats 6 – 8, sofa and loveseat, …see more

from $295 / night

$2000 / week

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Responds fast!
avg. 2 hours 50 minutes

from $295 / night

(1) Very Good 

24

Vacation home rental

Anna Maria Island / Holmes Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
617 Dundee - Private home 3 Bedroom / 3 Bath with private pool and boatdeck, maximum occupancy of 6 people. Hop out of the bed and into the pool! Lovely 3 bedroom, 3 bath home with newly remodeled kitchen. Screened pool on a canal with dock and davits. Enjoy the scre …see more

from $358 / night

$2500 - $2750 / week

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from $358 / night

1