Vacation rentals in Southside, FL

Best vacation rentals and Airbnb offers in Southside, FL

Landing Stylish 2BD Courtyard Gym

Apartment, Southside

Landing Stylish 2BD Courtyard Gym is a apartment in Southside. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Landing Stylish 2BD Courtyard Gym

Landing Stylish 2BD Courtyard Gym is a apartment in Southside. 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, ac, air conditioning, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $843.

From$92/night

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\"Mid-Century Studio\" Kitchenette, Wi-Fi

Apartment, Southside

\"Mid-Century Studio\" Kitchenette, Wi-Fi is a apartment in Southside, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About \"Mid-Century Studio\" Kitchenette, Wi-Fi

\"Mid-Century Studio\" Kitchenette, Wi-Fi is a apartment in Southside, with pet-friendly space, 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, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $734.

From$105/night

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Serene Bliss: Stylish 1BR Unit in Resort Complete

Apartment, Southside

Serene Bliss: Stylish 1BR Unit in Resort Complete is a apartment in Southside, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Serene Bliss: Stylish 1BR Unit in Resort Complete

Serene Bliss: Stylish 1BR Unit in Resort Complete is a apartment in Southside, 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, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $836.

From$119/night

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2-bedroom townhome in Bartram Park, full remote work set up.

Holiday Home, Southside

2-bedroom townhome in Bartram Park, full remote work set up. is a holiday home in Southside, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About 2-bedroom townhome in Bartram Park, full remote work set up.

2-bedroom townhome in Bartram Park, full remote work set up. is a holiday home in Southside, with pool 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: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $916.

From$131/night

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Vacation rentals with a pool in Southside, FL

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

Spacious 1BR Apt/Gym/Pool/Close 2 Beaches and Mayo

Apartment, Southside

Spacious 1BR Apt/Gym/Pool/Close 2 Beaches and Mayo is a apartment in Southside, with pool access, easy beach access, and room for a group. This stay gives travelers a comfortable base for…

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About Spacious 1BR Apt/Gym/Pool/Close 2 Beaches and Mayo

Spacious 1BR Apt/Gym/Pool/Close 2 Beaches and Mayo is a apartment in Southside, 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: free cancellation, gym, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,093.

From$156/night

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Lux King Bed Southside Pool Gym Near Mayo Beach

Apartment, Southside

Lux King Bed Southside Pool Gym Near Mayo Beach is a apartment in Southside, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Lux King Bed Southside Pool Gym Near Mayo Beach

Lux King Bed Southside Pool Gym Near Mayo Beach is a apartment in Southside, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,262.

From$180/night

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Spacious 1-BR, 2-King Beds, Near Mayo, Pool, Gym, Fast Wifi Workspace, Beach

Condo, Southside

Spacious 1-BR, 2-King Beds, Near Mayo, Pool, Gym, Fast Wifi Workspace, Beach is a condo in Southside, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Spacious 1-BR, 2-King Beds, Near Mayo, Pool, Gym, Fast Wifi Workspace, Beach

Spacious 1-BR, 2-King Beds, Near Mayo, Pool, Gym, Fast Wifi Workspace, Beach is a condo in Southside, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,303.

From$186/night

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Blue Bliss Luxury Stay

Apartment, Southside

Blue Bliss Luxury Stay is a apartment in Southside, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Blue Bliss Luxury Stay

Blue Bliss Luxury Stay is a apartment in Southside, with 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, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,337.

From$191/night

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Vacation rentals with parking in Southside, FL

Find vacation rentals that make arriving by car easier.

Charlotte's House

Homestay, Southside

Charlotte's House is a homestay in Southside, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Charlotte's House

Charlotte's House is a homestay in Southside, with 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 $613.

From$77/night

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Duplex Studio Center City covered parking full kitchen wash/dry self-check-in

Apartment, Southside

Duplex Studio Center City covered parking full kitchen wash/dry self-check-in is a apartment in Southside, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Duplex Studio Center City covered parking full kitchen wash/dry self-check-in

Duplex Studio Center City covered parking full kitchen wash/dry self-check-in is a apartment in Southside, with 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, hot tub, kitchen, with kitchen, and parking.

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

From$85/night

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La Casita by Amarelys and lazaro

Holiday Home, Southside

La Casita by Amarelys and lazaro is a holiday home in Southside, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About La Casita by Amarelys and lazaro

La Casita by Amarelys and lazaro is a holiday home in Southside, with 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 $683.

From$98/night

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Charming & Cozy 3 bedroom condo 15mn to Jacksonville beaches!

Condo, Southside

Charming & Cozy 3 bedroom condo 15mn to Jacksonville beaches! is a condo in Southside, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming & Cozy 3 bedroom condo 15mn to Jacksonville beaches!

Charming & Cozy 3 bedroom condo 15mn to Jacksonville beaches! is a condo in Southside, 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 $1,147.

From$164/night

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Pet-friendly vacation rentals in Southside, FL

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

King Bed Studio~ Near San Marco Nightlife &Dining~5 mins River

Holiday Home, Southside

King Bed Studio~ Near San Marco Nightlife &Dining~5 mins River is a holiday home in Southside, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About King Bed Studio~ Near San Marco Nightlife &Dining~5 mins River

King Bed Studio~ Near San Marco Nightlife &Dining~5 mins River is a holiday home in Southside, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $725.

From$104/night

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Mandarin Pearl Close to Everything!

Holiday Home, Southside

Mandarin Pearl Close to Everything! is a holiday home in Southside, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mandarin Pearl Close to Everything!

Mandarin Pearl Close to Everything! is a holiday home in Southside, with pet-friendly space 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $869.

From$124/night

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Stylish 2BR Townhouse - Near Hospitals, Dining & Hwy

Holiday Home, Southside

Stylish 2BR Townhouse - Near Hospitals, Dining & Hwy is a holiday home in Southside, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Stylish 2BR Townhouse - Near Hospitals, Dining & Hwy

Stylish 2BR Townhouse - Near Hospitals, Dining & Hwy is a holiday home in Southside, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,051.

From$150/night

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Enjoy this modern brand-new townhouse located in the heart of Jacksonville.

Holiday Home, Southside

Enjoy this modern brand-new townhouse located in the heart of Jacksonville. is a holiday home in Southside, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Enjoy this modern brand-new townhouse located in the heart of Jacksonville.

Enjoy this modern brand-new townhouse located in the heart of Jacksonville. is a holiday home in Southside, with 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 $1,155.

From$165/night

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Vacation rentals with a kitchen in Southside, FL

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

Charming 2-bedroom townhome with AC, WiFi in lovely Jacksonville

Holiday Home, Southside

Charming 2-bedroom townhome with AC, WiFi in lovely Jacksonville is a holiday home in Southside, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming 2-bedroom townhome with AC, WiFi in lovely Jacksonville

Charming 2-bedroom townhome with AC, WiFi in lovely Jacksonville is a holiday home in Southside, 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 $1,173.

From$168/night

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Luxe 2BR Townhome Close to Beach

Holiday Home, Southside

Luxe 2BR Townhome Close to Beach is a holiday home in Southside, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Luxe 2BR Townhome Close to Beach

Luxe 2BR Townhome Close to Beach is a holiday home in Southside, 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 $1,231.

From$176/night

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Stylish & Chic New 2BR Townhome

Holiday Home, Southside

Stylish & Chic New 2BR Townhome is a holiday home in Southside, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Stylish & Chic New 2BR Townhome

Stylish & Chic New 2BR Townhome is a holiday home in Southside, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,252.

From$179/night

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Elegant & Upscale 2BR Townhome

Holiday Home, Southside

Elegant & Upscale 2BR Townhome is a holiday home in Southside, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Elegant & Upscale 2BR Townhome

Elegant & Upscale 2BR Townhome is a holiday home in Southside, with 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 $1,356.

From$194/night

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Family-friendly vacation rentals in Southside, FL

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

EconoChic Hideaway, 2bd 2ba, Family Friendly, Washer and Dryer

Condo, Southside

EconoChic Hideaway, 2bd 2ba, Family Friendly, Washer and Dryer is a condo in Southside, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About EconoChic Hideaway, 2bd 2ba, Family Friendly, Washer and Dryer

EconoChic Hideaway, 2bd 2ba, Family Friendly, Washer and Dryer is a condo in Southside, with pet-friendly space, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,000.

From$143/night

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Family Home 5 Mi to Riverwalk & Jaguars Games!

Cottage, Southside

Family Home 5 Mi to Riverwalk & Jaguars Games! is a cottage in Southside, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Family Home 5 Mi to Riverwalk & Jaguars Games!

Family Home 5 Mi to Riverwalk & Jaguars Games! is a cottage in Southside, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,421.

From$150/night

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Spacious Jax Home Near Riverwalk & All Beaches

Cottage, Southside

Spacious Jax Home Near Riverwalk & All Beaches is a cottage in Southside, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Spacious Jax Home Near Riverwalk & All Beaches

Spacious Jax Home Near Riverwalk & All Beaches is a cottage in Southside, 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, free wifi, kitchen, with kitchen, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,579.

From$169/night

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Spacious Family Lodging on Florida's First Coast

Holiday Home, Southside

Spacious Family Lodging on Florida's First Coast is a holiday home in Southside, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Spacious Family Lodging on Florida's First Coast

Spacious Family Lodging on Florida's First Coast is a holiday home in Southside, with pool 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, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,371.

From$196/night

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