Vacation rentals in Leffis Key, FL

Best Vacation rentals and Airbnb offers in Leffis Key, FL

Updated 2B/2B with a beautiful view of the bay!

Condo, Leffis Key

Updated 2B/2B with a beautiful view of the bay! is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Updated 2B/2B with a beautiful view of the bay!

Updated 2B/2B with a beautiful view of the bay! is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,581.

From$112/night

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Bayview Condo B · Bay Views · Dock & Pool

Condo, Leffis Key

Bayview Condo B · Bay Views · Dock & Pool is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Bayview Condo B · Bay Views · Dock & Pool

Bayview Condo B · Bay Views · Dock & Pool is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,542.

From$116/night

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GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!

Condo, Leffis Key

GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!! is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!!

GORGEOUS UPSCALE LONGBOAT KEY CONDO OFFERS BAYFRONT VIEWS!! is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,578.

From$117/night

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Pelican Cove · Boat Dock · Bay & Gulf · Pool

Condo, Leffis Key

Pelican Cove · Boat Dock · Bay & Gulf · Pool is a condo in Leffis Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for…

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About Pelican Cove · Boat Dock · Bay & Gulf · Pool

Pelican Cove · Boat Dock · Bay & Gulf · Pool is a condo in Leffis Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,573.

From$122/night

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Browse Vacation Rentals with a Pool in Leffis Key, FL

Add a pool to the search when you want an easy place to cool off between outings.

Cozy Beach Studio – Silver Sands #251A by RVA

Apartment, Leffis Key

Cozy Beach Studio – Silver Sands #251A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Beach Studio – Silver Sands #251A by RVA

Cozy Beach Studio – Silver Sands #251A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,559.

From$148/night

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Beachfront Studio – Cabana #5B by RVA

Condo, Leffis Key

Beachfront Studio – Cabana #5B by RVA is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,559.

From$150/night

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Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people.

Condo, Leffis Key

Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people. is a condo in Leffis Key, with pool access, easy beach access, and room for a group.…

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About Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people.

Pelican Cove 5 - Anna Maria Island - Condo 2 Bedroom /2 Bath beach side, maximum occupancy of 5 people. is a condo in Leffis Key, with pool access, easy beach access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,284.

From$187/night

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Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people.

Condo, Leffis Key

Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people. is a condo in Leffis Key, with pool access, easy beach access, and room for a group.…

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About Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people.

Pelican Cove 9 - Anna Maria Island - Condo 2 Bedroom /2 Bath bay side, maximum occupancy of 5 people. is a condo in Leffis Key, with pool access, easy beach access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,389.

From$198/night

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Best Leffis Key, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Charming 2-bedroom house in gorgeous Longboat Key

Holiday Home, Leffis Key

Charming 2-bedroom house in gorgeous Longboat Key is a holiday home in Leffis Key, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Charming 2-bedroom house in gorgeous Longboat Key

Charming 2-bedroom house in gorgeous Longboat Key is a holiday home in Leffis Key, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,907.

From$184/night

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Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge

Condo, Leffis Key

Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge

Charming 1 Bd w/Pvt Lanai Steps to Beach/Bridge is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,896.

From$195/night

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Beach Unit w/Tropical Crtyd/Close to 2 Bridge St./

Condo, Leffis Key

Beach Unit w/Tropical Crtyd/Close to 2 Bridge St./ is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Beach Unit w/Tropical Crtyd/Close to 2 Bridge St./

Beach Unit w/Tropical Crtyd/Close to 2 Bridge St./ is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,896.

From$195/night

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Steps to Beach/Walk 2 Bridge St./Beach Supplies

Condo, Leffis Key

Steps to Beach/Walk 2 Bridge St./Beach Supplies is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Steps to Beach/Walk 2 Bridge St./Beach Supplies

Steps to Beach/Walk 2 Bridge St./Beach Supplies is a condo in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,928.

From$199/night

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Best Pet-Friendly Vacation Rentals in Leffis Key, FL

Bring your pet along with stays that welcome four-legged travelers.

Beach View - Sunset Landings Unit 2 by SeaBreeze Vacation

Condo, Leffis Key

Beach View - Sunset Landings Unit 2 by SeaBreeze Vacation is a condo in Leffis Key, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beach View - Sunset Landings Unit 2 by SeaBreeze Vacation

Beach View - Sunset Landings Unit 2 by SeaBreeze Vacation is a condo in Leffis Key, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,136.

From$189/night

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Beach View - Pelican Cove 3 by SeaBreeze Vacation

Condo, Leffis Key

Beach View - Pelican Cove 3 by SeaBreeze Vacation is a condo in Leffis Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About Beach View - Pelican Cove 3 by SeaBreeze Vacation

Beach View - Pelican Cove 3 by SeaBreeze Vacation is a condo in Leffis Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,149.

From$205/night

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Bayfront - Pelican Cove 16 by SeaBreeze Vacation

Condo, Leffis Key

Bayfront - Pelican Cove 16 by SeaBreeze Vacation is a condo in Leffis Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area,…

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About Bayfront - Pelican Cove 16 by SeaBreeze Vacation

Bayfront - Pelican Cove 16 by SeaBreeze Vacation is a condo in Leffis Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,153.

From$206/night

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Sunset Soul at Pelican Cove Unit 8 by SeaBreeze Vacation

Condo, Leffis Key

Sunset Soul at Pelican Cove Unit 8 by SeaBreeze Vacation is a condo in Leffis Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sunset Soul at Pelican Cove Unit 8 by SeaBreeze Vacation

Sunset Soul at Pelican Cove Unit 8 by SeaBreeze Vacation is a condo in Leffis Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,160.

From$207/night

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Best Leffis Key, FL vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

Affordable Beach Studio – Silver Sands #257A by RVA

Apartment, Leffis Key

Affordable Beach Studio – Silver Sands #257A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Affordable Beach Studio – Silver Sands #257A by RVA

Affordable Beach Studio – Silver Sands #257A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,581.

From$150/night

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Bright Beach Studio – Silver Sands #255A by RVA

Apartment, Leffis Key

Bright Beach Studio – Silver Sands #255A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Bright Beach Studio – Silver Sands #255A by RVA

Bright Beach Studio – Silver Sands #255A by RVA is a apartment in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,595.

From$152/night

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Bayview Condo C - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Distance to the Beach: 1 block

Condo, Leffis Key

Bayview Condo C - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Distance to the Beach: 1 block is a condo in Leffis Key, with pool access, easy beach…

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About Bayview Condo C - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Distance to the Beach: 1 block

Bayview Condo C - Anna Maria Island - Condo 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. Distance to the Beach: 1 block is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,386.

From$199/night

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Bayview Condo, Unit E - Anna Maria Island - 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people.

Condo, Leffis Key

Bayview Condo, Unit E - Anna Maria Island - 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. is a condo in Leffis Key, with pool access, easy beach access, and kitchen access.…

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About Bayview Condo, Unit E - Anna Maria Island - 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people.

Bayview Condo, Unit E - Anna Maria Island - 2 Bedroom/ 2 Bath bay view, maximum occupancy of 4 people. is a condo in Leffis Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,386.

From$199/night

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Our Favorite Family-Friendly Vacation Rentals in Leffis Key, FL

Plan a trip with stays that give families more room to spread out.

Live Oak Lodge | Private heated Pool Home Near Anna Maria Island | Family-Friendly Bradenton Vacation Rental | Sleeps 10 | Dog* (See Note) Allowed

Holiday Home, Leffis Key

Live Oak Lodge · Private heated Pool Home Near Anna Maria Island · Family-Friendly Bradenton Vacation Rental · Sleeps 10 · Dog* (See Note) Allowed is a holiday home in Leffis Key, with…

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About Live Oak Lodge | Private heated Pool Home Near Anna Maria Island | Family-Friendly Bradenton Vacation Rental | Sleeps 10 | Dog* (See Note) Allowed

Live Oak Lodge · Private heated Pool Home Near Anna Maria Island · Family-Friendly Bradenton Vacation Rental · Sleeps 10 · Dog* (See Note) Allowed is a holiday home in Leffis Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,135.

From$142/night

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Conch Cottage 1 Bedroom Villa by RedAwning

Holiday Home, Leffis Key

Conch Cottage 1 Bedroom Villa by RedAwning is a holiday home in Leffis Key, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Conch Cottage 1 Bedroom Villa by RedAwning

Conch Cottage 1 Bedroom Villa by RedAwning is a holiday home in Leffis Key, with pet-friendly space and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, bbq facilities, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,587.

From$188/night

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1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach!

Cottage, Leffis Key

1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach! is a cottage in Leffis Key, with easy beach access, kitchen access, and room for a group. This stay gives travelers a…

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About 1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach!

1BR West Unit of Beach to Bay Cottage...just 100 feet from Gulf Beach! is a cottage in Leffis Key, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,960.

From$200/night

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NEW LISTING... High Tide—- Beach and Bay just steps away!

Cottage, Leffis Key

NEW LISTING... High Tide—- Beach and Bay just steps away! is a cottage in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About NEW LISTING... High Tide—- Beach and Bay just steps away!

NEW LISTING... High Tide—- Beach and Bay just steps away! is a cottage in Leffis Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,275.

From$227/night

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