Longboat Key Beaches Pet Friendly Vacation Rentals

     

Condo

Perfect FL Longboat Key Getaway, steps from the Gulf! Sleeps 4

• Sarasota
• ·
• Longboat Key
• 0.74 mi to center

10.0

Exceptional

(11 Reviews)

1 Bedroom 1 Bath 4 Guests 657 ft²

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $131/Night 7 Nights - US $917

View Deal

     

Hotel

The St. Regis Longboat Key Resort

• Sarasota
• ·
• Longboat Key
• 2.20 mi to center

8.9

Fabulous

(32 Reviews)

11 Baths 673 ft²

• 
  Private Pool
• 
  Private Beach
• 
  Oceanfront
• 
  Hot Tub

US $874/Night 7 Nights - US $6,118

View Deal

      Highly Rated

Apartment

Sea Club I Beach Resort

• Sarasota
• ·
• Longboat Key
• 1.01 mi to center

9.2

Exceptional

(354 Reviews)

1 Bedroom 1 Bath 2 Guests

• 
  Parking
• 
  Pool
• 
  Ocean View
• 
  Balcony/Terrace

US $202/Night 7 Nights - US $1,414

View Deal

     

Condo

NEW Penthouse on the Bay - 2BR Condo Steps to Heated Pools, Tennis & Beach

• Sarasota
• ·
• Longboat Key
• 1.84 mi to center

10.0

Exceptional

(2 Reviews)

2 Bedrooms 2 Baths 4 Guests 1096 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $381/Night 7 Nights - US $2,668

View Deal

     

Apartment

Seaside Escape!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 4 Guests 409.03 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $343/Night 7 Nights - US $2,403

View Deal

      Highly Rated

Resort

Zota Beach Resort

• Sarasota
• ·
• Longboat Key
• 1.77 mi to center

9.2

Exceptional

(1006 Reviews)

1 Bath

• 
  Hot Tub
• 
  Breakfast
• 
  Pool
• 
  Ocean View

US $281/Night 7 Nights - US $1,968

View Deal

     

House

Tropical Escape–Private Pool Home Near the Sand Hy Tee on Longboat Key by RVA

• Sarasota
• ·
• Longboat Key
• 2.53 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 4 Guests 1700 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $284/Night 7 Nights - US $1,988

View Deal

     

Apartment

Island Time Open Sept 29th - Oct 3rd!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 333.68 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $437/Night 7 Nights - US $3,057

View Deal

     

Apartment

Sunset and beach view from your balcony Unit 501

• Sarasota
• ·
• Longboat Key
• 1.08 mi to center

1 Bedroom 1 Bath 4 Guests 700 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $426/Night 7 Nights - US $2,980

View Deal

     

Condo

Luxury Bayfront Condo | Stunning Views, Pools & Beach Across Street

• Sarasota
• ·
• Longboat Key
• 1.85 mi to center

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 5 Guests

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $267/Night 7 Nights - US $1,868

View Deal

     

Apartment

Beach Bliss!

• Sarasota
• ·
• Longboat Key
• 0.05 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 4 Guests 322.92 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $390/Night 7 Nights - US $2,728

View Deal

     

Condo

Steps from the Water with Spectacular Bay Views

• Sarasota
• ·
• Longboat Key
• 0.98 mi to center

9.8

Exceptional

(9 Reviews)

2 Bedrooms 2 Baths 6 Guests 1500 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Ocean View

US $288/Night 7 Nights - US $2,016

View Deal

     

Apartment

Top Floor Sunset Paradise Gulf View Unit 501

• Sarasota
• ·
• Longboat Key
• 1.08 mi to center

10.0

Exceptional

(2 Reviews)

1 Bedroom 1 Bath 6 Guests 699.65 ft²

• 
  Private Beach
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $418/Night 7 Nights - US $2,926

View Deal

      Price Dropped

Condo

Pet Friendly Longboat Key Condo with View of Gulf

• Sarasota
• ·
• Longboat Key
• 0.74 mi to center

9.6

Exceptional

(91 Reviews)

1 Bedroom 1 Bath 4 Guests 600 ft²

• 
  Oceanfront
• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace

US $118/Night 7 Nights - US $827

View Deal

     

Condo

Spectacular Sarasota Bay Views from all rooms

• Sarasota
• ·
• Longboat Key
• 1.60 mi to center

4.0

Average

(1 Review)

2 Bedrooms 2 Baths 4 Guests 1400 ft²

• 
  Parking
• 
  Pool
• 
  Spa
• 
  Ocean View

US $4,779/Night 7 Nights - US $33,451

View Deal

     

Condo

2-bedroom condo in beautiful Longboat Key with fitness room, AC

• Sarasota
• ·
• Longboat Key
• 1.22 mi to center

2 Bedrooms 2 Baths 6 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Ocean View

US $279/Night 7 Nights - US $1,950

View Deal

     

Villa

Longboat Key 1st Floor 2 bed/2 bath, Bayside Recreation-Beach Across the Street

• Sarasota
• ·
• Longboat Key
• 2.15 mi to center

2 Bedrooms 2 Baths 2 Guests 900 ft²

• 
  Air Conditioner
• 
  Internet
• 
  Pet Friendly
• 
  Child Friendly

US $182/Night 7 Nights - US $1,272

View Deal

     

House

UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY

• Sarasota
• ·
• Longboat Key
• 2.52 mi to center

10.0

Exceptional

(17 Reviews)

3 Bedrooms 2 Baths 6 Guests 2075 ft²

• 
  Private Pool
• 
  Parking
• 
  Pool
• 
  Ocean View

US $361/Night 7 Nights - US $2,529

View Deal

     

House

Longboat Key home on the canal and a 5 minute walk to the beach

• Sarasota
• ·
• Longboat Key
• 2.88 mi to center

10.0

Exceptional

(7 Reviews)

4 Bedrooms 3 Baths 8 Guests

• 
  Private Pool
• 
  Oceanfront
• 
  Parking
• 
  Pool

US $818/Night 7 Nights - US $5,725

View Deal

      Price Dropped

House

Suzie's Beach House, Longboat Key

• Sarasota
• ·
• Longboat Key
• 2.96 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests

• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

US $254/Night 7 Nights - US $1,779

View Deal

      Highly Rated

House

Luxurious beachfront house on exclusive LONGBOAT KEY. Directly on the beach!

• Sarasota
• ·
• Longboat Key
• 0.72 mi to center

9.6

Exceptional

(65 Reviews)

4 Bedrooms 2 Baths 8 Guests 3000 ft²

• 
  Parking
• 
  Ocean View
• 
  Balcony/Terrace
• 
  View

US $761/Night 7 Nights - US $5,330

View Deal

     

House

Charming 3-bedroom house in delightful Longboat Key with your own tiki bar

• Sarasota
• ·
• Longboat Key
• 2.77 mi to center

9.4

Exceptional

(6 Reviews)

3 Bedrooms 3 Baths 8 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $659/Night 7 Nights - US $4,615

View Deal

     

House

Bay Haven Home on Longboat Key by RVA

• Sarasota
• ·
• Longboat Key
• 2.93 mi to center

6.0

Good

(1 Review)

3 Bedrooms 2 Baths 6 Guests 1760 ft²

• 
  Private Pool
• 
  Oceanfront
• 
  Hot Tub
• 
  Parking

US $380/Night 7 Nights - US $2,662

View Deal

     

House

February 2027 NOW available! 3 minute walk to the beautiful white quartz sand.

• Sarasota
• ·
• Longboat Key
• 2.08 mi to center

6 Bedrooms 5 Baths 10 Guests

• 
  Private Pool
• 
  Hot Tub
• 
  Parking
• 
  Pool

US $1,422/Night 7 Nights - US $9,953

View Deal