Vacation rentals in Caladesi Island, FL

200 available vacation rental offers

airbnbBooking.comVrboExpediaSonderpricelineTripadvisorTrip.comHomestayHotels.comOrbitz

Choose the perfect vacation accommodation

Price per night

Up to $100$100 - 200From $200

Accommodation type

Vacation rentals

Rating

Excellent 9+Very good 8+Good 7+All ratings

Best Vacation rentals and Airbnb offers in Caladesi Island, FL

Sunny Side Cottages - Caladesi Island, FL

Sunny Side Cottages

Apartment, Caladesi Island

Sunny Side Cottages is a apartment in Caladesi Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

Read more

About Sunny Side Cottages

Sunny Side Cottages is a apartment in Caladesi Island, 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 $820.

From$93/night
Show
Sunny Side Cottages - Caladesi Island, FL

Sunny Side Cottages

Apartment, Caladesi Island

Sunny Side Cottages is a apartment in Caladesi Island, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

Read more

About Sunny Side Cottages

Sunny Side Cottages is a apartment in Caladesi Island, 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 $820.

From$93/night
Show
Spacious studio in Downtown Dunedin! Super Cute and Comfortable! - Caladesi Island, FL

Spacious studio in Downtown Dunedin! Super Cute and Comfortable!

Apartment, Caladesi Island

Spacious studio in Downtown Dunedin! Super Cute and Comfortable! is a apartment in Caladesi Island, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Spacious studio in Downtown Dunedin! Super Cute and Comfortable!

Spacious studio in Downtown Dunedin! Super Cute and Comfortable! is a apartment in Caladesi Island, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,098.

From$97/night
Show
Waterfront Studio at Beso del Sol | Pool, Balcony, Sunset Bar - Caladesi Island, FL

Waterfront Studio at Beso del Sol | Pool, Balcony, Sunset Bar

Apartment, Caladesi Island

Waterfront Studio at Beso del Sol · Pool, Balcony, Sunset Bar is a apartment in Caladesi Island, with pool access, easy beach access, and outdoor space. This stay gives travelers a…

Read more

About Waterfront Studio at Beso del Sol | Pool, Balcony, Sunset Bar

Waterfront Studio at Beso del Sol · Pool, Balcony, Sunset Bar is a apartment in Caladesi Island, with pool access, easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,167.

From$100/night
Show

Browse Waterfront Vacation Rentals in Caladesi Island, FL

Discover vacation rentals close to the coast, water, and beach areas around Caladesi Island, FL.

Charming 2-bedroom Close to the Beach in brilliant Palm Harbor - Caladesi Island, FL

Charming 2-bedroom Close to the Beach in brilliant Palm Harbor

Condo, Caladesi Island

Charming 2-bedroom Close to the Beach in brilliant Palm Harbor is a condo in Caladesi Island, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

Read more

About Charming 2-bedroom Close to the Beach in brilliant Palm Harbor

Charming 2-bedroom Close to the Beach in brilliant Palm Harbor is a condo in Caladesi Island, 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, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,045.

From$95/night
Show
Coastal 2BR Retreat Near Golf, Breweries & Beaches – Walk to Dining & Enjoy Local Adventures! - Caladesi Island, FL

Coastal 2BR Retreat Near Golf, Breweries & Beaches – Walk to Dining & Enjoy Local Adventures!

Condo, Caladesi Island

Coastal 2BR Retreat Near Golf, Breweries & Beaches – Walk to Dining & Enjoy Local Adventures! is a condo in Caladesi Island, with easy beach access, kitchen access, and room for a group.…

Read more

About Coastal 2BR Retreat Near Golf, Breweries & Beaches – Walk to Dining & Enjoy Local Adventures!

Coastal 2BR Retreat Near Golf, Breweries & Beaches – Walk to Dining & Enjoy Local Adventures! is a condo in Caladesi Island, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,253.

From$106/night
Show
Heart of Dunedin - Bay Suite: walk&ride everywhere - Caladesi Island, FL

Heart of Dunedin - Bay Suite: walk&ride everywhere

Apartment, Caladesi Island

Heart of Dunedin - Bay Suite: walk&ride everywhere is a apartment in Caladesi Island, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Heart of Dunedin - Bay Suite: walk&ride everywhere

Heart of Dunedin - Bay Suite: walk&ride everywhere is a apartment in Caladesi Island, 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 $1,242.

From$141/night
Show
2-bedroom on Clearwater Beach. One block to the beach. - Caladesi Island, FL

2-bedroom on Clearwater Beach. One block to the beach.

Holiday Home, Caladesi Island

2-bedroom on Clearwater Beach. One block to the beach. is a holiday home in Caladesi Island, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable…

Read more

About 2-bedroom on Clearwater Beach. One block to the beach.

2-bedroom on Clearwater Beach. One block to the beach. is a holiday home in Caladesi Island, with pet-friendly space, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,516.

From$146/night
Show

Browse Vacation Rentals with a Pool in Caladesi Island, FL

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

Dunedin Condo on the Water - Caladesi Island, FL

Dunedin Condo on the Water

Condo, Caladesi Island

Dunedin Condo on the Water is a condo in Caladesi Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Dunedin Condo on the Water

Dunedin Condo on the Water is a condo in Caladesi Island, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,343.

From$143/night
Show
Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes - Caladesi Island, FL

Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes

Condo, Caladesi Island

Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes is a condo in Caladesi Island, with pool access and easy beach access. This stay gives travelers a comfortable…

Read more

About Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes

Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes is a condo in Caladesi Island, 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 $1,449.

From$144/night
Show
Key West Style Cottage - with pool/hot-tub - Caladesi Island, FL

Key West Style Cottage - with pool/hot-tub

Cottage, Caladesi Island

Key West Style Cottage - with pool/hot-tub is a cottage in Caladesi Island, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub is a cottage in Caladesi Island, with pool 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, pool, hot tub, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,362.

From$144/night
Show
Coastal Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! - Caladesi Island, FL

Coastal Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Holiday Home, Caladesi Island

Coastal Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, with pool access and kitchen access. This stay gives travelers a…

Read more

About Coastal Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Coastal Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,415.

From$145/night
Show

Best Caladesi Island, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access - Caladesi Island, FL

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access

Apartment, Caladesi Island

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access is a apartment in Caladesi Island, with pool access, parking, and kitchen access. This stay gives travelers a…

Read more

About Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access

Charming studio & kitchenette in wonderful Palm Harbor with AC & laundry access is a apartment in Caladesi Island, with pool 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, pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $665.

From$73/night
Show
Near Fishing: Palm Harbor Studio w/ Pool Access! - Caladesi Island, FL

Near Fishing: Palm Harbor Studio w/ Pool Access!

Apartment, Caladesi Island

Near Fishing: Palm Harbor Studio w/ Pool Access! is a apartment in Caladesi Island, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Near Fishing: Palm Harbor Studio w/ Pool Access!

Near Fishing: Palm Harbor Studio w/ Pool Access! is a apartment in Caladesi Island, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $934.

From$79/night
Show
Downtown Dunedin! 2 bedroom 2 bath - Caladesi Island, FL

Downtown Dunedin! 2 bedroom 2 bath

Apartment, Caladesi Island

Downtown Dunedin! 2 bedroom 2 bath is a apartment in Caladesi Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About Downtown Dunedin! 2 bedroom 2 bath

Downtown Dunedin! 2 bedroom 2 bath is a apartment in Caladesi Island, 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 $1,247.

From$121/night
Show
2 Bedroom Apt Overlooking Dunedin Town Square - Caladesi Island, FL

2 Bedroom Apt Overlooking Dunedin Town Square

Apartment, Caladesi Island

2 Bedroom Apt Overlooking Dunedin Town Square is a apartment in Caladesi Island, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About 2 Bedroom Apt Overlooking Dunedin Town Square

2 Bedroom Apt Overlooking Dunedin Town Square is a apartment in Caladesi Island, 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 $1,275.

From$131/night
Show

Best Pet-Friendly Vacation Rentals in Caladesi Island, FL

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

Modern Loft Downtown - Caladesi Island, FL

Modern Loft Downtown

Holiday Home, Caladesi Island

Modern Loft Downtown is a holiday home in Caladesi Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Modern Loft Downtown

Modern Loft Downtown is a holiday home in Caladesi Island, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,237.

From$129/night
Show
Downtown Dunedin Hideaway / Easy Walk to Downtown! - Caladesi Island, FL

Downtown Dunedin Hideaway / Easy Walk to Downtown!

Holiday Home, Caladesi Island

Downtown Dunedin Hideaway / Easy Walk to Downtown! is a holiday home in Caladesi Island, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Downtown Dunedin Hideaway / Easy Walk to Downtown!

Downtown Dunedin Hideaway / Easy Walk to Downtown! is a holiday home in Caladesi Island, 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 $1,363.

From$132/night
Show
Stay in Downtown Dunedin • Walk Everywhere - Caladesi Island, FL

Stay in Downtown Dunedin • Walk Everywhere

Cottage, Caladesi Island

Stay in Downtown Dunedin · Walk Everywhere is a cottage in Caladesi Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Stay in Downtown Dunedin • Walk Everywhere

Stay in Downtown Dunedin · Walk Everywhere is a cottage in Caladesi Island, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,360.

From$141/night
Show
Downtown Dunedin Cottage • Walk to Restaurants - Caladesi Island, FL

Downtown Dunedin Cottage • Walk to Restaurants

Cottage, Caladesi Island

Downtown Dunedin Cottage · Walk to Restaurants is a cottage in Caladesi Island, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Downtown Dunedin Cottage • Walk to Restaurants

Downtown Dunedin Cottage · Walk to Restaurants is a cottage in Caladesi Island, 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,382.

From$144/night
Show

Best Caladesi Island, FL vacation rentals with a kitchen

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

Winter Availability! Escape the snow! 2 BR in Sunny Downtown Dunedin! ☀️ - Caladesi Island, FL

Winter Availability! Escape the snow! 2 BR in Sunny Downtown Dunedin! ☀️

Holiday Home, Caladesi Island

Winter Availability! Escape the snow! 2 BR in Sunny Downtown Dunedin! ☀️ is a holiday home in Caladesi Island, with parking, kitchen access, and room for a group. This stay gives travelers…

Read more

About Winter Availability! Escape the snow! 2 BR in Sunny Downtown Dunedin! ☀️

Winter Availability! Escape the snow! 2 BR in Sunny Downtown Dunedin! ☀️ is a holiday home in Caladesi Island, 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 $1,655.

From$154/night
Show
Farm House Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! - Caladesi Island, FL

Farm House Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Holiday Home, Caladesi Island

Farm House Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, with pool access and kitchen access. This stay gives travelers…

Read more

About Farm House Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Farm House Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, 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 $1,580.

From$155/night
Show
Waterfront Resort Condo – Clearwater Beaches & Honeymoon Island, Sunset, Bikes - Caladesi Island, FL

Waterfront Resort Condo – Clearwater Beaches & Honeymoon Island, Sunset, Bikes

Condo, Caladesi Island

Waterfront Resort Condo – Clearwater Beaches & Honeymoon Island, Sunset, Bikes is a condo in Caladesi Island, with pool access, easy beach access, and kitchen access. This stay gives…

Read more

About Waterfront Resort Condo – Clearwater Beaches & Honeymoon Island, Sunset, Bikes

Waterfront Resort Condo – Clearwater Beaches & Honeymoon Island, Sunset, Bikes is a condo in Caladesi Island, 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 $1,585.

From$158/night
Show
Rustic Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! - Caladesi Island, FL

Rustic Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Holiday Home, Caladesi Island

Rustic Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, with pool access, parking, and kitchen access. This stay gives…

Read more

About Rustic Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin!

Rustic Tiny Home on Pinellas Trail w/ Heated Pool! Walk or Bike to Downtown Dunedin! is a holiday home in Caladesi Island, with pool 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,610.

From$158/night
Show