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Anna Maria Island Beach Vacation Rentals, Beach Rentals & More - 19 Rentals Available.

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19 Vacation rentals

Filters applied: Beach

(2)

1 / 22

Anna Maria House

  • 8
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is simply amazing. There is nothing that could be improved upon. The house is gorgeous, clean, and very welcoming. The pool was the bomb as was the hot tub in the evenings! The best part of the pool is that it has all day sun which...”
- Review left on 04/22/2016

$599

Excellent (2 reviews)

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from $599 / night

1 / 21

Anna Maria House

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$500

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from $500 / night

1 / 81

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$200

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from $200 / night

(19)

1 / 27

Anna Maria House

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$175

Very Good (19 reviews)

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from $175 / night

1 / 25

Anna Maria Island Cottage

  • 1
  • 3
  • 1 night min
  • Beach/lakeside relaxation

$200

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from $200 / night

(1)

1 / 20

Bradenton Beach Cottage

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

$150

Very Good (1 reviews)

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from $150 / night

(68)

1 / 67

Bradenton Beach Cottage

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We were suppose to go to West Palm Beach and the hurricane at that time changed our plans and we decided to look around at a place I had been to before--Anna Maria Island. We found this ad on the Sugar Shack and we were lucky it was not rented the...”
- Review left on 02/22/2017

$214

Excellent (68 reviews)

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from $214 / night

(28)

1 / 97

Bradenton Beach Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$250

Very Good (28 reviews)

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from $250 / night

1 / 20

Bradenton Beach Condo

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$272

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from $272 / night

(1)

1 / 44

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was our first time renting, we usually stay at a hotel. The unit was exactly like the photos and clean as well. I had some trouble with the garbage disposal so I called the property management and they were very professional and offer to put...”
- Review left on 07/05/2016

$150

Excellent (1 reviews)

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from $150 / night

(5)

1 / 92

Anna Maria Island Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$250

Very Good (5 reviews)

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from $250 / night

(5)

1 / 93

Anna Maria Island House

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$350

Excellent (5 reviews)

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from $350 / night

(6)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$329

Excellent (6 reviews)

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from $329 / night

(2)

1 / 20

Bradenton Beach Cottage

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$135

Excellent (2 reviews)

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from $135 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$500

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from $500 / night

(1)

1 / 78

Anna Maria Island Condo

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$120

Excellent (1 reviews)

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from $120 / night

1 / 53

Holmes Beach House

  • 6
  • 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $350 / night

1 / 21

Anna Maria House

  • 5
  • 11
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$600

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from $600 / night

1 / 21

Anna Maria House

  • 5
  • 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

$700

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from $700 / night

Your search has been expanded 17.1 miles to include more rentals

(2)

1 / 11

Bradenton Apartment - 2.3 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$74

Excellent (2 reviews)

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from $74 / night

1 / 29

Cortez Townhouse - 2.8 miles away

  • 4
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$295

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from $295 / night

(4)

1 / 60

Bradenton Villa - 3.4 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We just returned from our stay in the Bayfront Villa. My husband, two teenagers and my 92-yr old Mother in law found this location to be perfect for us. My two kids thoroughly enjoyed fishing off of the dock, swimming in the pool and swimming off...”
- Review left on 06/23/2015

$213

Excellent (4 reviews)

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from $213 / night

1 / 17

Longboat Key House - 4.8 miles away

  • 6
  • 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

$600

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from $600 / night

1 / 28

Longboat Key Condo - 6.7 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $155 / night

(1)

1 / 14

Longboat Key Townhouse - 7 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

$122

Excellent (1 reviews)

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from $122 / night

(21)

1 / 32

Palmetto House - 7.5 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“Two days after we arrived, we booked for 2018! Capt Julie and Pamela have made an enchanted, whimsical oasis where you can find a mermaid sitting on a bench in the garden, a charming metal tortoise lounging by the pool and an open, flowing old...”
- Review left on 02/20/2017

$300

Excellent (21 reviews)

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from $300 / night

(1)

1 / 22

Longboat Key Condo - 7.8 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
“This was a family holiday including 2 grandchildren, who loved every minute of the holiday and did not want to leave. Lovely 3 bedrooms condo in garden grounds, which lead to the beach, family swimming pool and adult pool and spa. 8 tennis courts....”
- Review left on 01/26/2017

$100

Very Good (1 reviews)

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from $100 / night

(2)

1 / 16

Sarasota Condo - 10.7 miles away

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Child friendly
“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$79

Very Good (2 reviews)

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from $79 / night

1 / 8

Sarasota Condo - 10.7 miles away

  • 1
  • 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Ask about children

$49

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from $49 / night

1 / 8

Sarasota Condo - 10.7 miles away

  • 1
  • 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Ask about children

$45

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from $45 / night

(8)

1 / 24

Longboat Key Condo - 11 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Enjoyed a 7 night stay in this well furnished 1 bedroom condominium. The owner provided everything to make our stay very comfortable in a very well kept unit. The pool area and grounds are all well maintained We were in walking distance to the...”
- Review left on 12/29/2016

$115

Excellent (8 reviews)

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from $115 / night

(25)

1 / 24

Bradenton House - 12.9 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$120

Excellent (25 reviews)

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from $120 / night

(20)

1 / 108

St. Petersburg Condo - 13 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“We had stayed all around Florida , but Never had a view like this, water everywhere, from all the windows. When you see the pictures they are gorgeous but in real life Wow. I think this is one of the best condo's we have stayed in. The owners are...”
- Review left on 05/30/2017

$135

Excellent (20 reviews)

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from $135 / night

(5)

1 / 15

Bradenton Villa - 13.1 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This villa was everything you could want and more , had everything you could need down to beach chairs provided to take on the beach , it was in a peaceful surroundings overlooking a lake at the back and very comfortable inside would recommend this...”
- Review left on 09/29/2015

$133

Very Good (5 reviews)

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from $133 / night

(11)

1 / 22

Bradenton House - 13.3 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house was lovely ~ spacious, clean, comfortable, & convenient to everything. The pool was great. Neighborhood was quiet ~ loved looking out over the lake. Great view from the living room. This was perfect for me and my family and we had...”
- Review left on 05/31/2016

$130

Very Good (11 reviews)

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from $130 / night

(6)

1 / 24

St. Pete Beach House - 13.7 miles away

  • 2
  • 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

$123

Excellent (6 reviews)

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from $123 / night

(17)

1 / 22

St. Pete Beach House - 13.7 miles away

  • 1
  • 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

$105

Excellent (17 reviews)

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from $105 / night

(22)

1 / 26

Bradenton Villa - 13.7 miles away

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had a great experience renting this home in July 2016. House was comfortable, pool area was relaxing, and the lake presented good fishing every morning and evening, from right behind the house. Plenty of convenient restaurants nearby, and Siesta...”
- Review left on 01/01/2017

$200

Excellent (22 reviews)

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from $200 / night

(1)

1 / 39

St. Petersburg Apartment - 13.9 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$129

Excellent (1 reviews)

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from $129 / night

(4)

1 / 33

St. Petersburg Apartment - 13.9 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$129

Excellent (4 reviews)

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from $129 / night

(1)

1 / 40

St. Petersburg Apartment - 13.9 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$84

Excellent (1 reviews)

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from $84 / night

(1)

1 / 43

St. Petersburg Apartment - 14 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$70

Excellent (1 reviews)

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from $70 / night

(1)

1 / 27

St. Petersburg Apartment - 14 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$122

Excellent (1 reviews)

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from $122 / night

1 / 41

St. Petersburg Apartment - 14 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

from $122 / night

(1)

1 / 39

St. Pete Beach Apartment - 14 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$122

Excellent (1 reviews)

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from $122 / night

(4)

1 / 45

St. Pete Beach House - 14.1 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We can not say enough of this absolutely wonderful home! Betty was so helpful and accommodating! We had everything we needed right there in the home! The pier was such a fun experience. Our kids loved fishing and dolphin watching! The house is...”
- Review left on 07/04/2017

$357

Excellent (4 reviews)

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from $357 / night

1 / 34

St. Petersburg Apartment - 14.2 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

from $122 / night

(1)

1 / 33

St. Petersburg Apartment - 14.2 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$122

Excellent (1 reviews)

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from $122 / night

(2)

1 / 20

Longboat Key Condo - 14.2 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The Longboat Beach Club was a beautiful vacation location! The hotel room was the best I ever had. The beach was picture perfect, the food was excellent and the weather could not have been better. I thought I was vacationing in heaven! Thank you!...”
- Review left on 10/05/2015

$300

Very Good (2 reviews)

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from $300 / night

(13)

1 / 17

St. Pete Beach Condo - 14.7 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The views from the patio are incredible! The sunsets are so beautiful and you can hang out and watch the dolphins go by. Only a short walk to the ocean. Paradise at St Pete Beach...”
- Review left on 03/16/2017

$180

Very Good (13 reviews)

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from $180 / night

(12)

1 / 23

Bradenton House - 15.5 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$215

Excellent (12 reviews)

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from $215 / night

(1)

1 / 23

Sarasota House - 15.6 miles away

  • 4
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We spent a week at this property & absolutely loved it. Even our kids (ages 21 & 25) were saying best time ever. We had planned to do a couple day trips to the Orlando area and only ended up leaving the area once (to Universal) because no one...”
- Review left on 10/16/2014

$343

Excellent (1 reviews)

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from $343 / night

(16)

1 / 12

Bradenton House - 15.9 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Superbly equipped villa in a great location. Immaculately clean with high spec kitchen which was equipped extremely well with good quality appliances. Pool area nice with fab spa overlooking lake and big outside dining area which was used all the...”
- Review left on 08/07/2016

$193

Excellent (16 reviews)

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from $193 / night

(1)

1 / 18

St. Petersburg Condo - 15.9 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My family and I stayed in this condo back in February of 2016. We had a great experience! This condo is very clean, comfortable, and nicely decorated. We all loved having breakfast and evening drinks on the patio. The pool area is also very clean....”
- Review left on 04/29/2017

$100

Excellent (1 reviews)

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from $100 / night

1 / 26

Sarasota House - 16.1 miles away

  • 6
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $586 / night

(3)

1 / 8

Bradenton Villa - 16.2 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$164

Very Good (3 reviews)

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from $164 / night

(1)

1 / 13

St. Pete Beach Condo - 16.2 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$176

Very Good (1 reviews)

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from $176 / night

(23)

1 / 46

St. Petersburg Manor house - 17.1 miles away

  • 7
  • 21
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
“We invited our extended family to spend Christmas together this year at The Petro Mansion, hoping that the house looked as good in person as it did online. The house is just as beautiful, if not more so, in person! Alex had the house beautifully...”
- Review left on 01/02/2017

$1099

Excellent (23 reviews)

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from $1099 / night

(49)

1 / 21

Treasure Island Condo - 17.1 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“First and foremost, Nick was easily the most wonderful owner we have ever dealt with. He was quick to get back with us on any email and very pleasant. The condo is perfectly located on the beach, minutes from everything and walking distance to Caddy'...”
- Review left on 04/05/2017

$142

Excellent (49 reviews)

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from $142 / night