Vacation rentals in Pine Key, FL

Best Vacation rentals and Airbnb offers in Pine Key, FL

Tropical Pass-A-Grille Gem w/ Direct Beach Access!

Apartment, Pine Key

Tropical Pass-A-Grille Gem w/ Direct Beach Access! is a apartment in Pine Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Tropical Pass-A-Grille Gem w/ Direct Beach Access!

Tropical Pass-A-Grille Gem w/ Direct Beach Access! is a apartment in Pine 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, beachfront, and beach front.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $973.

From$65/night

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Tropical Pass-A-Grille Gem w/ Direct Beach Access!

Apartment, Pine Key

Tropical Pass-A-Grille Gem w/ Direct Beach Access! is a apartment in Pine Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Tropical Pass-A-Grille Gem w/ Direct Beach Access!

Tropical Pass-A-Grille Gem w/ Direct Beach Access! is a apartment in Pine Key, with easy beach access and parking. 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, beachfront, beach front, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $943.

From$69/night

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Unit 3 Blocks Gulf to Beaches Historical Museum!

Apartment, Pine Key

Unit 3 Blocks Gulf to Beaches Historical Museum! is a apartment in Pine Key, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Unit 3 Blocks Gulf to Beaches Historical Museum!

Unit 3 Blocks Gulf to Beaches Historical Museum! is a apartment in Pine 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 cancellation, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,169.

From$75/night

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Unit 3 Blocks Gulf to Beaches Historical Museum!

Apartment, Pine Key

Unit 3 Blocks Gulf to Beaches Historical Museum! is a apartment in Pine Key, with easy beach access and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Unit 3 Blocks Gulf to Beaches Historical Museum!

Unit 3 Blocks Gulf to Beaches Historical Museum! is a apartment in Pine Key, with easy beach access and parking. 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, free wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,212.

From$89/night

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Browse Vacation Rentals with a Pool in Pine Key, FL

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

Five star Stunning Remodel On Bay, Close to Beach, Discount for Long-term!

Condo, Pine Key

Five star Stunning Remodel On Bay, Close to Beach, Discount for Long-term! is a condo in Pine Key, with pool access and easy beach access. This stay gives travelers a comfortable base for…

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About Five star Stunning Remodel On Bay, Close to Beach, Discount for Long-term!

Five star Stunning Remodel On Bay, Close to Beach, Discount for Long-term! is a condo in Pine 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 $1,492.

From$147/night

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Renovated 6/2023 Top Floor Balcony Water View 2B/2B, Pool, Hot Tub, Grill, WIFI

Condo, Pine Key

Renovated 6/2023 Top Floor Balcony Water View 2B/2B, Pool, Hot Tub, Grill, WIFI is a condo in Pine Key, with pool access and outdoor space. This stay gives travelers a comfortable base for…

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About Renovated 6/2023 Top Floor Balcony Water View 2B/2B, Pool, Hot Tub, Grill, WIFI

Renovated 6/2023 Top Floor Balcony Water View 2B/2B, Pool, Hot Tub, Grill, WIFI is a condo in Pine Key, with pool access and outdoor space. 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 $1,771.

From$165/night

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Waterfront Relaxing Condo-heated pool & spa- near Fort Desoto

Condo, Pine Key

Waterfront Relaxing Condo-heated pool & spa- near Fort Desoto is a condo in Pine Key, with pool access, easy beach access, and a quieter setting. This stay gives travelers a comfortable…

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About Waterfront Relaxing Condo-heated pool & spa- near Fort Desoto

Waterfront Relaxing Condo-heated pool & spa- near Fort Desoto is a condo in Pine Key, with pool access, easy beach access, and a quieter setting. 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,592.

From$166/night

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Camelot by the Sea by Liberte'

Condo, Pine Key

Camelot by the Sea by Liberte' is a condo in Pine Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Camelot by the Sea by Liberte'

Camelot by the Sea by Liberte' is a condo in Pine 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: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,593.

From$188/night

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Best Pine Key, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Bungalow Bleu

Homestay, Pine Key

Bungalow Bleu is a homestay in Pine Key, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Bungalow Bleu

Bungalow Bleu is a homestay in Pine Key, with pet-friendly space and parking. 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $272.

From$34/night

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St Pete Studio Rooms

Homestay, Pine Key

St Pete Studio Rooms is a homestay in Pine Key, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About St Pete Studio Rooms

St Pete Studio Rooms is a homestay in Pine Key, with pet-friendly space and parking. 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, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $325.

From$41/night

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Coastal Haven

Homestay, Pine Key

Coastal Haven is a homestay in Pine Key, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Coastal Haven

Coastal Haven is a homestay in Pine Key, with parking. 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, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $338.

From$42/night

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Beach Getaway in Beautiful Pass A Grille Florida

Condo, Pine Key

Beach Getaway in Beautiful Pass A Grille Florida is a condo in Pine Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Beach Getaway in Beautiful Pass A Grille Florida

Beach Getaway in Beautiful Pass A Grille Florida is a condo in Pine 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,856.

From$180/night

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Best Pet-Friendly Vacation Rentals in Pine Key, FL

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

60 seconds to Private Beach Rated #1 in Florida /Pets welcome with fee

Condo, Pine Key

60 seconds to Private Beach Rated #1 in Florida /Pets welcome with fee is a condo in Pine Key, with pet-friendly space and easy beach access. This stay gives travelers a comfortable base…

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About 60 seconds to Private Beach Rated #1 in Florida /Pets welcome with fee

60 seconds to Private Beach Rated #1 in Florida /Pets welcome with fee is a condo in Pine Key, with pet-friendly space 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: hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,774.

From$185/night

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Freshly Remodeled, Cozy 1-bedroom studio in serene St. Pete Beach with AC

Apartment, Pine Key

Freshly Remodeled, Cozy 1-bedroom studio in serene St. Pete Beach with AC is a apartment in Pine Key, with pet-friendly space, easy beach access, and room for a group. This stay gives…

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About Freshly Remodeled, Cozy 1-bedroom studio in serene St. Pete Beach with AC

Freshly Remodeled, Cozy 1-bedroom studio in serene St. Pete Beach with AC is a apartment in Pine Key, with pet-friendly space, 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: free cancellation, washer, dryer, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,919.

From$200/night

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Walk to The Best Restaurants, Beaches, and Activities. Heated Pool. Fabulous Location.

Condo, Pine Key

Walk to The Best Restaurants, Beaches, and Activities. Heated Pool. Fabulous Location. is a condo in Pine Key, with pool access, easy beach access, and kitchen access. This stay gives…

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About Walk to The Best Restaurants, Beaches, and Activities. Heated Pool. Fabulous Location.

Walk to The Best Restaurants, Beaches, and Activities. Heated Pool. Fabulous Location. is a condo in Pine 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 $1,998.

From$201/night

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La Tortuga Historic Downtown Pass A Grille St Pete Beach 4

Apartment, Pine Key

La Tortuga Historic Downtown Pass A Grille St Pete Beach 4 is a apartment in Pine Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About La Tortuga Historic Downtown Pass A Grille St Pete Beach 4

La Tortuga Historic Downtown Pass A Grille St Pete Beach 4 is a apartment in Pine 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$206/night

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Best Pine Key, FL vacation rentals with a kitchen

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

Tiny House , Big Vibes Illuminated Backyard Escape

Holiday Home, Pine Key

Tiny House , Big Vibes Illuminated Backyard Escape is a holiday home in Pine Key, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Tiny House , Big Vibes Illuminated Backyard Escape

Tiny House , Big Vibes Illuminated Backyard Escape is a holiday home in Pine 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 $996.

From$107/night

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Beachfront on Pass-A-Grille Beach with Pool! Walking Distance to Great Restaurants and Shops.

Condo, Pine Key

Beachfront on Pass-A-Grille Beach with Pool! Walking Distance to Great Restaurants and Shops. is a condo in Pine Key, with pool access, easy beach access, and kitchen access. This stay…

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About Beachfront on Pass-A-Grille Beach with Pool! Walking Distance to Great Restaurants and Shops.

Beachfront on Pass-A-Grille Beach with Pool! Walking Distance to Great Restaurants and Shops. is a condo in Pine 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 $1,990.

From$201/night

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La Tortuga Historic Downtown Pass A Grille St Pete Beach 5

Apartment, Pine Key

La Tortuga Historic Downtown Pass A Grille St Pete Beach 5 is a apartment in Pine Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About La Tortuga Historic Downtown Pass A Grille St Pete Beach 5

La Tortuga Historic Downtown Pass A Grille St Pete Beach 5 is a apartment in Pine 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$206/night

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La Tortuga Historic Downtown Pass A Grille St Pete Beach 6

Apartment, Pine Key

La Tortuga Historic Downtown Pass A Grille St Pete Beach 6 is a apartment in Pine Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable…

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About La Tortuga Historic Downtown Pass A Grille St Pete Beach 6

La Tortuga Historic Downtown Pass A Grille St Pete Beach 6 is a apartment in Pine 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$206/night

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

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

Rock Lobster 1 | Cozy Beach Cottage Steps from Treasure Island Beach & John’s Pass

Holiday Home, Pine Key

Rock Lobster 1 · Cozy Beach Cottage Steps from Treasure Island Beach & John’s Pass is a holiday home in Pine Key, with easy beach access, parking, and kitchen access. This stay gives…

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About Rock Lobster 1 | Cozy Beach Cottage Steps from Treasure Island Beach & John’s Pass

Rock Lobster 1 · Cozy Beach Cottage Steps from Treasure Island Beach & John’s Pass is a holiday home in Pine 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 ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,107.

From$92/night

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Rock Lobster 2 | Beachside Cottage in Treasure Island FL – Steps to Beach & John’s Pass

Holiday Home, Pine Key

Rock Lobster 2 · Beachside Cottage in Treasure Island FL – Steps to Beach & John’s Pass is a holiday home in Pine Key, with easy beach access, parking, and kitchen access. This stay gives…

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About Rock Lobster 2 | Beachside Cottage in Treasure Island FL – Steps to Beach & John’s Pass

Rock Lobster 2 · Beachside Cottage in Treasure Island FL – Steps to Beach & John’s Pass is a holiday home in Pine 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 $1,070.

From$92/night

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Happy Hour ACROSS THE STREET FROM THE BEACH

Cottage, Pine Key

Happy Hour ACROSS THE STREET FROM THE BEACH is a cottage in Pine Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Happy Hour ACROSS THE STREET FROM THE BEACH

Happy Hour ACROSS THE STREET FROM THE BEACH is a cottage in Pine 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,502.

From$158/night

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easy access to beach, large family retreat, huge outdoor area

Holiday Home, Pine Key

easy access to beach, large family retreat, huge outdoor area is a holiday home in Pine Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable…

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About easy access to beach, large family retreat, huge outdoor area

easy access to beach, large family retreat, huge outdoor area is a holiday home in Pine 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 $1,618.

From$161/night

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