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Luxury Vacation Rentals in Longboat Key

(67 rentals)
Anna Maria Island House
Sleeps 12, 6 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

110 11th Street South - Bradenton Beach - FL 34217 No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60...

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Featured review

"Family vacation"

The house was beautiful, lots of space to spread out with a family of 12. Location was perfect, beach on one side and bay on the other. Had everything we needed for cooking, pool, and relaxing. Pool was...

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$935
avg per night
Bradenton House
Sleeps 12, 5 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Bay House Retreat by Beach Retreats Vacation Rentals Sarasota Bayfront – Near IMG Academy & Downtown Sarasota 5 Bedrooms | 4 Bathrooms | Sleeps 12 | Heated Saltwater Pool | 2 Private Docks Welcome to Bay House Retreat, a luxurious bayfront escape offering over 4,000 sq. ft. of comfort...

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Featured review

"Beautiful Place"

Four siblings and their spouses enjoyed this spacious home for a week. Right at the water’s edge, with a great pool and spa, it was like a self-contained resort of its own. The views of sunrise and...

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$773
avg per night
Anna Maria Island Condo
Sleeps 10, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Sunset Penthouse at Bradenton Beach Club, where top-floor luxury meets picture-perfect Gulf views. Step into the family room and be greeted by sweeping panoramas of Bradenton Beach. This 4-bedroom, 2.5-bathroom penthouse is thoughtfully designed for comfort, style, and effortless coastal...

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$711
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$1,046
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 4 bathrooms
20 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Breathe Inn, your island escape where the sea breeze is plentiful and the relaxation comes naturally. This beautifully renovated 5-bedroom, 3.5-bath duplex with 2 kitchens invites you to exhale and settle into vacation mode. With two fully private units under one roof, it's the perfect...

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Featured review

"Breathe Inn"

Wonderful property and perfect for families with kids. The house was clean, well appointed with everything you could possibly need, and comfortable for everyone. The pool was always clean and well maintained....

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$760
avg per night

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Anna Maria Island House
Sleeps 12, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$810
avg per night
Bradenton House
Sleeps 19, 5 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Retreat at Palma Sola Bay your Waterfront Oasis! 150+ Feet of Direct Palma Sola Bay Waterfront Private Heated Pool & Spa (Pool Heat Included) Private Dock – Fish, Kayak, Paddleboard or Bring Your Boat Separate Guest House + Game Room Sleeps 19 Guests Comfortably Walk...

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Featured review

"Perfect"

We were a group of soccer moms (and one dad) there for a few days for a tournament. This house was everything we could have wanted! Clean, well appointed, excellent location, I can't say enough! Nights...

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$824
avg per night
Bradenton House
Sleeps 19, 8 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "The Plantation House"! Short drive to the World Class Beaches of Anna Maria Island Private Enclosed Heated Pool/Spa, Game Room, Boat Dock, & more! Walk to the Palma Sola Causeway/ Jet Ski Rentals, Kayak rentals, and Horseback Riding! Close proximity to Lakewood Ranch,...

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$804
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Paradise Found - with Pool & Hot Tub 401 42nd Street, Holmes Beach, FL 34217 VRC17-000010 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub ​​​​​​​ Pet Friendly This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation...

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Featured review

"Paradise Found"

We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard...

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$856
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Beach House – Luxury 5-Bedroom Retreat with Pool & Jacuzzi 403 42nd Street, Holmes Beach, FL 34217 VRC 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to Paradise...

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$845
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Location, Location, Location Staying near the Holmes Beach public beach means you get the best of the island without the hassle: Easy, stress-free beach access (no long walks or parking) Nearby public amenities like restrooms, showers & lifeguards Walk to restaurants, cafes & beach...

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$732
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Angel Sea by Beach Retreats Vacation Rentals VRC19-000188 4118 5th Ave, Holmes Beach, FL 34217 6 Bedrooms | 3.5 Bathrooms | Sleeps 12 | Elevator | Heated Pool & Hot Tub This home can park up to 4 vehicles Welcome to Angel Sea—a stunning 6-bedroom, 3.5-bathroom vacation home designed...

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Featured review

"Family vacation"

House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.

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$743
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Located in the heart of Holmes Beach on Anna Maria Island, this 4-bedroom, 5.5-bath coastal getaway is your dream vacation home — perfect for families, friends, or group trips. Short walk to the beach Private mini putt-putt + game room Heated pool + spa oasis Close to bars, dining, and...

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$790
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
7 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island! As you step through the front door, you enter a bright and...

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$717
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Footprints in the Sand 114 48th Street Holmes Beach FL 34217 VRC19-000156 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Pet Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome to FootPrints in the Sand, a stunning vacation...

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$753
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Just Beachy – Your Luxury Island Retreat on Anna Maria Island 128 49th Street Holmes Beach FL 34217 VRC21-000019 4 Bedrooms + nanny suite | 6 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub | This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Escape...

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Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its...

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$966
avg per night
Bradenton House
Sleeps 23, 8 bedrooms, 7.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to 75 Palms! Short drive to the World Class Beaches of Anna Maria Island Private Gated Oasis: 2 Houses, 1 Lot, 8 Bedrooms Heated Pool, Hot Tub, Outdoor Kitchen, BBQ Grill Pickleball Court, 3 Hole Putting Green, Fire Pit & More! Game Room:98 in Smart TV, Billiards, Foosball, Arcade...

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Featured review

"Senior Families Spring Break Trip"

75 Palms was amazing! We had a group of 21 people for a senior boys spring break trip, and it was perfect. The outdoor area is very big, and there’s a lot to do. The swimming pool is a great size, the...

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$824
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$712
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Island Escape by Beach Retreats Vacation Rentals 307 65th St, Holmes Beach, FL 34217 VRC18-000047 Your dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions....

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Featured review

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly...

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$858
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290 4 Bedrooms | 4.5 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Welcome...

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Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally...

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$1,092
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC16-000137 Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida. This ground level beach house offers 4 bedrooms,...

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Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing....

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$748
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach! Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...

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$1,087
avg per night
Anna Maria Island Townhome
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Oasis by the Beach by Beach Retreats Vacation Rentals 202 69th St, Holmes Beach, FL 34217 VRC17-000120 5 Bedrooms | 4 Bathrooms | Sleeps 10 | Heated Pool & Hot Tub This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors Book with confidence: No cancellation...

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Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were...

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$822
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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Featured review

"Better than i expected."

Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.

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$729
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...

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Featured review

"Family vacation"

We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...

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$741
avg per night
Sarasota House
Sleeps 8, 4 bedrooms, 4 bathrooms
4 reviews

Distance to beach: 0.1 miles to Lido

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

St. Armand's Canal-Front Pool Home steps to the beach! This gem, ranch style home estate has been completely rebuilt and remodeled in 2015 from the frame including all new finishes inside and out. With fresh, coastal Old-Florida decor, it is in one of the most desirable locations on the west...

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$1,046
avg per night
New
Sarasota House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Stunning waterfront home located on popular Lido Key. Situated directly on the picturesque canal, this home is perfect for boating enthusiasts or anyone who appreciates the beauty and serenity of waterfront living. Get ready to enjoy your days lounging by the pool, sitting around the outdoor fire pit,...

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$875
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Limefish Luxury | Premier Gulf-Front Living & Iconic Sunsets True beachfront luxury with a private heated pool. Wake up to unobstructed Gulf views, step directly onto the sand, and enjoy total privacy in this stunning 3BR/3BA coastal retreat. Perfect for romantic escapes, work-from-the-beach stays,...

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$1,755
avg per night
Sarasota House
Sleeps 12, 5 bedrooms, 5 bathrooms
8 reviews

Distance to beach: 0.1 miles to Lido

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Lovely remodeled and refurbished 5 bedroom 5.5 bath pool home on desirable St. Armand's Circle! This 3,000 s.f. home comfortably sleeps (8) in beds, and has T.V.'s in the family room and living room for when the family is not enjoying the caged pool and spa. Professionally decorated, quality...

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$800
avg per night
New
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Reef Romance special: - Concierge Collection Property - Golf cart included! - Three houses from beautiful beaches on Anna Maria - Heated pool / separate covered spa, outdoor shower - Grill (propane included) - Putt-putt golf - Professional Linen Services - Complimentary...

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$766
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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$803
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! Welcome to your home-away-from-home, a 4-bedroom, 4 full bath, and 1 half bath pet-friendly canal-front retreat designed for unforgettable stays. With beautiful water views and space for families, friends, or fishing trips, Yacht Sea the perfect...

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$886
avg per night
Sarasota Condo
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Immerse yourself in beachfront bliss at Lido Bliss: Imagine stepping off the elevator into your private sanctuary. Breathtaking panoramic views of the Gulf of Mexico greet you from your expansive balcony, setting the scene for an unforgettable stay. This meticulously kept, 4-bedroom 3.5 bath haven exudes...

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$835
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Bimini Sunrise special: - Concierge Collection Property - Golf cart included! - Anna Maria on Anna Maria Island - A short walk to Pine Avenue - Spacious heated pool / spa - Rooftop deck, elevator, private dock - Gas grill (propane included) - Professional Linen Service -...

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$1,023
avg per night
Bradenton House
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxury Beach Home • Steps to Sandbar Restaurant • Elevator • Sleeps 10 • Pets Welcome Welcome to Villa Del Sol, a luxury Anna Maria Island vacation rental located just two houses from the beach and steps from the iconic Sandbar Restaurant. With Gulf views, heated swim spa, private...

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$710
avg per night
Anna Maria Island House
Sleeps 10, 6 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxury Beach Home • Gulf Views • Heated Pool • Steps to Beach • Sleeps 10 Welcome to Sunset Paradise, a stunning Anna Maria Island vacation home located just three houses from the Gulf and steps from the beach. With breathtaking Gulf views, a private heated pool, and multiple balconies...

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$848
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
2 reviews

Distance to beach: 0.1 miles to Bayside Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms and 3 Bathrooms...

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Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...

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$838
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
77 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Bayfront Pool Retreat + Walk to Pine Ave + Golf Cart | Tripletail Welcome to Tripletail, your bayfront escape on the coveted north end of Anna Maria Island — where peaceful waterfront views, walkability to Pine Avenue, and resort-style outdoor living come together for an unforgettable stay. Perfectly...

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Featured review

"Paradise by the sea!"

Beautiful, outstanding home with unbelievable views from every window! The water is right outside your door. Plus there's a hot tub out back and a pool out front. It was a very memorable trip that I'll...

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$1,495
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

NO CANCELLATION FEES: $500 deposit due at time of booking; balance due 60 days prior to arrival Cancel 60+ days before arrival → Full refund (no fees). Cancel within 60 days of arrival → No refund. Cancellations must be made in writing and received by Beach Retreats on or before the...

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Featured review

"Excellent place to stay!"

This house was incredible! Absolutely beautiful, well stocked, an amazing pool and outdoor setup, and so conveniently located! While it's not beach-front, it's just a house or two away from the beach entrance...

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$802
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
58 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Waterfront Pool Retreat + Dock & Boat Lift + Golf Cart | Beach Bliss Welcome to Beach Bliss, your waterfront escape on Anna Maria Island — where relaxed luxury, boating adventures, and effortless island living come together for an unforgettable stay. This beautifully designed 4-bedroom,...

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$987
avg per night
Anna Maria Island House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared Dock Luxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...

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$892
avg per night
Anna Maria Island House
Sleeps 12, 5 bedrooms, 5 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Vitamin Sea by Beach Retreats Vacation Rentals 146 Crescent Dr, Anna Maria, FL 34216 Welcome to Vitamin Sea, a stunning 5-bedroom, 5-bath luxury retreat located on the coveted north end of Anna Maria Island, just a 10-minute stroll to Bean Point Beach. With a private dock, heated saltwater pool and...

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Featured review

"Paradise"

Vitamin Sea exceeded all expectations for our week's vacation for our family of 12. Location was perfect for daily visits to both sides of the island. House is stunning and fully equipped for swimming,...

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$992
avg per night
Sarasota House
Sleeps 14, 5 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Glamor Manor, your luxurious retreat in the heart of Sarasota, Florida! This exquisite vacation rental offers an unparalleled experience of comfort, style, and relaxation. Property Highlights: Pet friendly : $200 non-refundable pet fee Heated Swimming Pool: Dive into luxury with our private...

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$753
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Sandcastle – Beachside Escape with Heated Pool, Golf Cart & Island Adventure Gear 3 Bedrooms | 2.5 Bathrooms | Heated Pool | Golf Cart | Bikes | Paddle Boards | Kayaks | Steps to the Beach Welcome to Sandcastle, your perfect Anna Maria Island beach retreat. Ideally located just across...

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$815
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
63 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Steps to Beach + Heated Pool + Putting Green + Golf Cart | Waves Welcome to Waves, your beautifully remodeled coastal retreat on Anna Maria Island — where modern luxury, effortless beach access, and resort-style outdoor living create the ultimate island escape. Perfectly positioned just across...

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$1,000
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also...

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Featured review

"The perfect getaway"

The entire stay was above all expectations. It was my wife's birthday. We invited friends from out of town to celebrate with us. The place was roomy and very comfortable. The kitchen is fantastic with the...

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$1,310
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers...

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$892
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms
39 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beachfront Luxury + Pool Deck + Complimentary Golf Cart | Cloud 9 Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group...

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Featured review

"Paradise!"

This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!

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$2,199
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
70 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beachfront boho escape on Anna Maria Island NEW heated Gulfside pool + hot tub with sunset views 4BR layout with private cottage for extra space & privacy Steps to the sand + paddle boards, bikes & INCLUDED 6-passenger golf cart Serene north-end location — the island retreat guests...

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$1,435
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
76 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Private Pool Oasis + Beach Volleyball Court + INCLUDED Golf Cart | Fanta-Sea Escape to Fanta-Sea, your private tropical retreat on the coveted north end of Anna Maria Island — where backyard fun, beachside relaxation, and effortless island exploring come together. Step through your back gate...

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$1,409
avg per night
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