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

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2,089 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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from $94 / night

(13) Very Good 

12

Apartment rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Beachy and bright condo on the second floor of a small 2-story-building (20 units in total), overlooking the mangroves with view to the Palma Sola Bay. Only some steps away from the ocean and the wonderful wide and powder sanded beaches. The condo is recently refurnishe …see more

from $105 / night

$700 - $1,400 / week

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from $105 / night

29

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Make this beautiful 3-bedroom, 2.5-bath vacation rental house your new home-away-from-home in Holmes Beach! Up to 6 travelers will have the luxury of swimming in the private pool or hot tub after kayaking in Palma Sola Bay. Take the provided wagon to the Gulf Beach a me …see more

from $235 / night

$1,645 - $2,800 / week

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avg. 52 minutes

from $235 / night

(28) Excellent 

Certificate of Excellence

52

Vacation home rental

Anna Maria Island / Holmes Beach

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • 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

Certificate of Excellence

from $269 / night

$1,883 / week

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Responds fast!
avg. 54 minutes

from $269 / night

31

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience casual island luxury at this Holmes Beach getaway. Boasting plenty of room for the whole crew and even the family dog (for a small nightly fee), this getaway has it all. Stay in the heart of the island and enjoy a tropical shared pool with a 10-foot waterfall …see more

from $136 / night

$952 / week

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avg. 1 hour 19 minutes

from $136 / night

28

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Make this Mediterranean-style home with a private lagoon-shaped pool, jetted tub, and easy beach access your home away from home when you come to Anna Maria Island. Come revel in luxury and local flavor! Located in the heart of Holmes Beach, yet tucked away from the hu …see more

from $136 / night

$952 / week

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avg. 1 hour 19 minutes

from $136 / night

(2) Excellent 

21

Condo rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 14 nights min

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The number 3 island in the United States so says Trip Advisor. The best island beach sand so says Conde Nast Travelers. So who wouldn't want to stay right on the beach in an immaculate and roomy 2 bedroom, 2 bath condominium in the Tiffany Place Condominium located on …see more

from $179 / night

$1,250 / week

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from $179 / night

(2) Excellent 

15

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Come relax and enjoy your beach vacation at The Dolphin Club! 2 bedrooms and 1 bathroom, the master bedroom has a queen bed and the other has 2 twin beds. There is also a sleeper couch in the living room which can sleep 2 people. Fully air conditioned. Includes covered …see more

from $110 / night

$700 - $900 / week

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avg. 38 minutes

from $110 / night

35

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
This cozy duplex with a shared pool and easy beach access is waiting for your upcoming Anna Maria Island vacation. You'll be in close proximity to dining and shopping, and you'll have space to park two cars. This rental is located two blocks from flour soft, sugar whi …see more

from $122 / night

$854 / week

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Responds fast!
avg. 1 hour 19 minutes

from $122 / 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 $225 / night

$1,240 / week

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avg. 3 hours 12 minutes

from $225 / night

11

Vacation townhouse in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything! Salt Air West , located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island. Not in the mo …see more

from $149 / night

$999 - $2,499 / week

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from $149 / night

(22) 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 $229 / night

$1,600 - $2,500 / week

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from $229 / night

56

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
To see a video tour of this home, click here. Experience luxury living at this three-bedroom seaside home with a fireplace, tropical accents, casually sophisticated decor, and updated amenities. Spend lazy days by the heated pool or stroll out to the adjacent Gulf-fron …see more

from $286 / night

$2,002 / week

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Responds fast!
avg. 1 hour 19 minutes

from $286 / night

(5) Very Good 

24

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 - $1,350 / week

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Responds fast!
avg. 3 hours 7 minutes

from $150 / night

24

Vacation home in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the nort …see more

from $122 / night

$854 / week

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Responds fast!
avg. 1 hour 19 minutes

from $122 / 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 $145 / night

$795 - $1,350 / week

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from $145 / night

32

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 3 Bedroom/ 3 Bath, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. VRC16-000070 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 …see more

from $122 / night

$850 - $1,760 / week

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from $122 / night

17

Vacation condo in Holmes Beach

Anna Maria Island / Holmes Beach

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Child friendly
Three bedroom condo directly overlooking the Gulf of Mexico. Watch the dolphins while eating your breakfast or the beautiful Gulf sunsets over wine or while eating dinner. Master bedroom has a king size bed and en suite bathroom with shower and walk-in closet. Second …see more

from $185 / night

$1,295 / week

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from $185 / 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 - $1,350 / week

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Responds fast!
avg. 3 hours 3 minutes

from $150 / night

18

Vacation apartment 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 $165 / night

$885 - $1,390 / week

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Responds fast!
avg. 3 hours 7 minutes

from $165 / night

(1) Very Good 

26

Vacation villa in Holmes Beach

Anna Maria Island / Holmes Beach

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Find everything that makes a fun beach getaway on Anna Maria Island memorable when you stay at North Gulf Villa Beach vacation rental home 6311 North Beach Village. This three bedroom townhouse style vacation rental sleeps up to eight guests, and is just a short walk to …see more

from $399 / night

$2,500 - $3,500 / week

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from $399 / night

(3) Excellent 

30

Vacation condo rental

Anna Maria Island / Holmes Beach

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Location! location! Spacious and light 1395 sq.ft, 2 bed, 2 bath condo on Anna Maria Island in Holmes Beach. Located on a quiet, less traveled fork of Gulf drive. No roads to cross, you can see the beach at sunset from your lanai or roof deck. Right out #3's door and up …see more

from $165 / night

$1,150 - $1,500 / week

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Responds fast!
avg. 3 hours 57 minutes

from $165 / night

11

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Sandy Point 205 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 4 people. Distance to the Beach: 4 blocks. VRC16-000291 Sit on your balcony and listen to the gentle sway of the mangroves as you sip on your cocktail and bask in the Florida warmth! 2 bedroom, 2 bath con …see more

from $135 / night

$700 - $1,430 / week

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from $135 / 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 $136 / night

$950 / week

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from $136 / night

(3) Very Good 

13

Cottage rental in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This cottage is located "on the beach" 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street …see more

from $180 / night

$1,140 / week

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Responds fast!
avg. 1 hour 52 minutes

from $180 / 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 - $1,350 / week

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Responds fast!
avg. 3 hours 7 minutes

from $150 / night

22

Vacation villa in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Recently renovated, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. Located in a quiet neighborhood with an easy 3-minute walk to the gorgeous white sand beaches of the Gulf of Mexico. You are less than a mile from historic Pine Avenue sho …see more

from $165 / night

$1,050 - $1,600 / week

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from $165 / night

18

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 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

$1,090 - $1,695 / week

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Responds fast!
avg. 3 hours 3 minutes

from $200 / night

31

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Your ultimate Florida getaway starts right here at this ideally located 2-bedroom, 2-bathroom vacation rental condo situated right on the beach. Boasting 1,500 square feet and accommodations for up to 6, this open concept condo offers direct access to Holmes Beach and w …see more

from $185 / night

$1,295 - $1,715 / week

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Responds fast!
avg. 2 hours 3 minutes

from $185 / night

(5) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $105 / night

$700 - $1,350 / week

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from $105 / night

(2) Good 

12

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Island Beach Club 4 - Condo 2 Bedroom / 1 Bath ground level gulf front , maximum occupancy of 4 people. Community pool. VRC16-000066 Gulf Coast's Finest!~ Looking for the ultimate Gulf front luxury vacation? Well, look no further. You will love this ground level 2 b …see more

from $192 / night

$900 - $1,500 / week

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from $192 / night

(1) Excellent 

34

Vacation apartment with shared pool in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
Harbor Lane Court Harmony - Condo 2 Bedroom / 2 Bath 2 blocks from the beach, maximum occupancy of 6 people. VRC16-000031 Harbor Lane Court is a 4 unit resort, with 3 one bedroom, one bath apartments, and one two bedroom, 2 bath apartment. Just newly renovated, all uni …see more

from $144 / night

$900 - $1,600 / week

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from $144 / night

(4) Very Good 

14

Vacation apartment in Holmes Beach

Anna Maria Island / Holmes Beach

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living …see more

from $185 / night

$1,295 / week

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from $185 / night

(4) Very Good 

14

Holmes Beach Vacation home rental

Anna Maria Island / Holmes Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fu …see more

from $300 / night

$2,100 / week

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from $300 / night

(2) Excellent 

22

Holmes Beach Vacation cottage rental

Anna Maria Island / Holmes Beach

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • 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

$1,300 / week

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Responds fast!
avg. 1 hour 32 minutes

from $199 / night

(8) Excellent 

26

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 - $1,050 / week

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from $125 / night

(3) 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

$895 / week

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from $128 / 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

$1,090 - $1,695 / week

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Responds fast!
avg. 3 hours 3 minutes

from $200 / night

(14) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $150 / night

$1,050 - $1,650 / week

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Responds fast!
avg. 2 hours 45 minutes

from $150 / night

(4) Very Good 

26

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

$1,980 / week

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Responds fast!
avg. 3 hours 12 minutes

from $300 / night