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Longboat Key Family & Kid Friendly Rentals

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429 rentals in Longboat Key.
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Las Hermanas/Starfish #3 Beach front Longboat Key, vacation rental in Longboat Key

Las Hermanas/Starfish #3 Beach front Longboat Key

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachfront Studio #1 Longboat Key, vacation rental in Longboat Key

Beachfront Studio #1 Longboat Key

0 bedrooms
1 bathroom
Sleeps 4
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Unit #210 Sand Cay Beach Resort Pool and Garden View, vacation rental in Longboat Key

Unit #210 Sand Cay Beach Resort Pool and Garden View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Unit 4, Cozy Getaway for two, vacation rental in Longboat Key

Beachfront Unit 4, Cozy Getaway for two

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Las Hermanas/Starfish #2 Beachfront Longboat Key, vacation rental in Longboat Key

Las Hermanas/Starfish #2 Beachfront Longboat Key

1 bedroom
1 bathroom
Sleeps 4
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Unit #105 Sand Cay Beach Resort Gulf View, vacation rental in Longboat Key

Unit #105 Sand Cay Beach Resort Gulf View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Zilli Tower 503, vacation rental in Longboat Key

Zilli Tower 503

1 bedroom
1 bathroom
Sleeps 6
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Amazing beachfront View & balcony on Longboat Key, vacation rental in Longboat Key

Amazing beachfront View & balcony on Longboat Key

1 bedroom
1 bathroom
Sleeps 4
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Beautiful Beach Views that will let you see 2020 in a whole new perspective, vacation rental in Longboat Key

Beautiful Beach Views that will let you see 2020 in a whole new perspective

2 bedrooms
2 bathrooms
Sleeps 6
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ZILLI VILLA, vacation rental in Longboat Key

ZILLI VILLA

2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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DOLPHIN HOUSE  Luxury on Water - Canal - Dock - boat lift, vacation rental in Longboat Key

DOLPHIN HOUSE Luxury on Water - Canal - Dock - boat lift

3 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly on Longboat Key, vacation rental in Longboat Key

Pet Friendly on Longboat Key

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Breathtaking Beach Front Property Ground Floor Condo, vacation rental in Longboat Key

Breathtaking Beach Front Property Ground Floor Condo

2 bedrooms
2 bathrooms
Sleeps 6
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Steps from Beach or Bay, vacation rental in Longboat Key

Steps from Beach or Bay

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Outrigger 9 Gulf Front first level walk out to the beach  Oct-Nov $195 per night, vacation rental in Longboat Key

Outrigger 9 Gulf Front first level walk out to the beach Oct-Nov $195 per night

1 bedroom
1 bathroom
Sleeps 2
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Hidden Bay/Beach Paradise, vacation rental in Longboat Key

Hidden Bay/Beach Paradise

4 bedrooms
4 bathrooms
Sleeps 8
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Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*, vacation rental in Longboat Key

Upscale Beachplace Condo w/ Gulf & Bay Views *DEC 2020 OPEN*

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Unit #309 Enjoy great rates, just steps to the sandy beach!, vacation rental in Longboat Key

Unit #309 Enjoy great rates, just steps to the sandy beach!

2 bedrooms
2 bathrooms
Sleeps 6
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PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH, vacation rental in Longboat Key

PRIVATE BEACHFRONT HOUSE ON EXCLUSIVE LONGBOAT KEY - DIRECTLY ON THE BEACH

4 bedrooms
4 bathrooms
Sleeps 8
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Penthouse Condo with Awesome Views !, vacation rental in Longboat Key

Penthouse Condo with Awesome Views !

2 bedrooms
2 bathrooms
Sleeps 6
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Beachcomber unit 303, vacation rental in Longboat Key

Beachcomber unit 303

1 bedroom
1 bathroom
Sleeps 4
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Tranquil waterfront with heated pool, dock and walk to beach, vacation rental in Longboat Key

Tranquil waterfront with heated pool, dock and walk to beach

4 bedrooms
4 bathrooms
Sleeps 8
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Fine Living Relaxation and Enjoyment! Enjoy Beach and Sunsets, vacation rental in Longboat Key

Fine Living Relaxation and Enjoyment! Enjoy Beach and Sunsets

3 bedrooms
3 bathrooms
Sleeps 8
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Love the Beach? Love tennis? The pool? Great family home with many amenities!, vacation rental in Longboat Key

Love the Beach? Love tennis? The pool? Great family home with many amenities!

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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A little piece of Paradise! Exceptional Reviews!, vacation rental in Longboat Key

A little piece of Paradise! Exceptional Reviews!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor, vacation rental in Longboat Key

Private Beach Cottage On The North End Of LBK. 2 Bedrooms 1 Bath On 2nd Floor

2 bedrooms
1 bathroom
Sleeps 6
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Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK, vacation rental in Longboat Key

Ground Floor 2 Beds 1 bath beach cottage short walk to beach on North end LBK

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Longboat Vacation Home w/ gorgeous views-  Walk to Beach, vacation rental in Longboat Key

Luxurious Longboat Vacation Home w/ gorgeous views- Walk to Beach

5 bedrooms
7 bathrooms
Sleeps 10
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Pet Friendly Longboat Key Condo with View of Gulf, vacation rental in Longboat Key

Pet Friendly Longboat Key Condo with View of Gulf

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6, vacation rental in Longboat Key

Cabana Beach Club #2: 2 BR / 2 BA Resort on Longboat Key by RVA, Sleeps 6

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Longboat Key Beachfront - Beautifully Updated with Prime Location, vacation rental in Longboat Key

Longboat Key Beachfront - Beautifully Updated with Prime Location

2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly Longboat Key Condo - Steps from Beach !!, vacation rental in Longboat Key

Pet Friendly Longboat Key Condo - Steps from Beach !!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean., vacation rental in Longboat Key

Sea Grape Inn #6-Beautiful! BEACHVIEW, steps from ocean.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Condo in Longboat Key Resort: Pool, Tennis, Bikes, Beach Access!!, vacation rental in Longboat Key

Spacious Condo in Longboat Key Resort: Pool, Tennis, Bikes, Beach Access!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Can't Get Closer to the Beach Without Getting Your Feet Wet!, vacation rental in Longboat Key

Can't Get Closer to the Beach Without Getting Your Feet Wet!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Zilli Ocean Front 101, vacation rental in Longboat Key

Zilli Ocean Front 101

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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NO REGRETS! Bright elevated beautiful sunny home.  Quick walk to beach and bay., vacation rental in Longboat Key

NO REGRETS! Bright elevated beautiful sunny home. Quick walk to beach and bay.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean., vacation rental in Longboat Key

Sea Grape Inn #7-Beautiful BEACHVIEW property, steps from ocean.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 BED/2 BATH GROUND FLOOR BEACHFRONT CONDO ON THE GULF OF MEXICO, vacation rental in Longboat Key

2 BED/2 BATH GROUND FLOOR BEACHFRONT CONDO ON THE GULF OF MEXICO

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft, vacation rental in Longboat Key

Cedars East Unit #521 2BR/2.5BA Condo Longboat Key- updated- 1440 sqft

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite 2BR/2BA Condo with Beach/Gulf View, vacation rental in Longboat Key

Exquisite 2BR/2BA Condo with Beach/Gulf View

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access, vacation rental in Longboat Key

Beach Escape to Longboat Key, Waterfront Sunrises/Sunsets, Gulf Beach Access

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Beach Place 6th floor penthouse with ocean and bay views., vacation rental in Longboat Key

Beach Place 6th floor penthouse with ocean and bay views.

2 bedrooms
2 bathrooms
Sleeps 6
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Silver Sands #254: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, vacation rental in Longboat Key

Silver Sands #254: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO  ~, vacation rental in Longboat Key

~ SPECIALS FROM $99 ~ OCEAN FRONT DLX STUDIO ~

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Your Vacation Oasis Awaits on Beautiful Longboat Key!, vacation rental in Longboat Key

Your Vacation Oasis Awaits on Beautiful Longboat Key!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Beach View, Heated Pool, Tennis Courts, vacation rental in Longboat Key

Spectacular Beach View, Heated Pool, Tennis Courts

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5, vacation rental in Longboat Key

The Beach on Longboat Key #227: 1 BR / 1 BA Resort by RVA, Sleeps 5

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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WATERFRONT  PRIVATE DOCK, LONGBOAT KEY FLORIDA 1000 FEET TO THE BEACH, vacation rental in Longboat Key

WATERFRONT PRIVATE DOCK, LONGBOAT KEY FLORIDA 1000 FEET TO THE BEACH

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Silver Sands #252: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4, vacation rental in Longboat Key

Silver Sands #252: 1 BR / 1 BA Resort on Longboat Key by RVA, Sleeps 4

1 bedroom
1 bathroom
Sleeps 4
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Beachfront condos and bayside villas – your vacation rental on Longboat Key
Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.
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Beachfront condos and bayside villas – your vacation rental on Longboat Key
Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.
Longboat Key - the upscale coastal vacation destination
This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.
Cultural treasures along Sarasota Bay
Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.
Waterfront dining
Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.
Visitor reviews aid vacation rental selection
You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.