Vacation rentals in Saddlebunch Keys, FL

Best Vacation rentals and Airbnb offers in Saddlebunch Keys, FL

Sugarloaf Key RV Resort & Cottages

Holiday Home, Saddlebunch Keys

Sugarloaf Key RV Resort & Cottages is a holiday home in Saddlebunch Keys, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Saddlebunch Keys, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,210.

From$139/night

Show›

Sugarloaf Key RV Resort & Cottages

Holiday Home, Saddlebunch Keys

Sugarloaf Key RV Resort & Cottages is a holiday home in Saddlebunch Keys, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages is a holiday home in Saddlebunch Keys, with pet-friendly space, 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, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,199.

From$171/night

Show›

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage, Saddlebunch Keys

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Saddlebunch Keys, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

Read more

About Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West! is a cottage in Saddlebunch Keys, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,394.

From$199/night

Show›

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cottage, Saddlebunch Keys

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Saddlebunch Keys, with pet-friendly space, pool access, and easy beach access. This stay gives…

Read more

About Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West! is a cottage in Saddlebunch Keys, 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, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,460.

From$209/night

Show›

Browse Vacation Rentals with a Pool in Saddlebunch Keys, FL

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

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Holiday Home, Saddlebunch Keys

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon is a holiday home in Saddlebunch Keys, with pool access and easy beach access. This stay gives travelers a…

Read more

About Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon

Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon is a holiday home in Saddlebunch Keys, 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 $1,670.

From$239/night

Show›

Enjoy Caribbean weather in the USA. Openings June 2026 forward!

Holiday Home, Saddlebunch Keys

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Saddlebunch Keys, with pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Enjoy Caribbean weather in the USA. Openings June 2026 forward!

Enjoy Caribbean weather in the USA. Openings June 2026 forward! is a holiday home in Saddlebunch Keys, 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 $1,754.

From$251/night

Show›

Seas The Day in Cudjoe Key

Holiday Home, Saddlebunch Keys

Seas The Day in Cudjoe Key is a holiday home in Saddlebunch Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Seas The Day in Cudjoe Key

Seas The Day in Cudjoe Key is a holiday home in Saddlebunch Keys, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,775.

From$254/night

Show›

Ocean Breeze Retreat w/ Dock - Keys Escape

Holiday Home, Saddlebunch Keys

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Saddlebunch Keys, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Ocean Breeze Retreat w/ Dock - Keys Escape

Ocean Breeze Retreat w/ Dock - Keys Escape is a holiday home in Saddlebunch Keys, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,800.

From$257/night

Show›

Best Saddlebunch Keys, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Key West - Stock Island

Holiday Home, Saddlebunch Keys

Key West - Stock Island is a holiday home in Saddlebunch Keys, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Key West - Stock Island

Key West - Stock Island is a holiday home in Saddlebunch Keys, 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: pool, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,083.

From$298/night

Show›

Starlight Serenity - Hideaway w Stunning Views

Holiday Home, Saddlebunch Keys

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Saddlebunch Keys, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the…

Read more

About Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views is a holiday home in Saddlebunch Keys, 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 wifi, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,521.

From$402/night

Show›

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

Condo, Saddlebunch Keys

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking is a condo in Saddlebunch Keys, with pool access, easy beach access, and parking. This stay gives travelers a…

Read more

About 3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking

3 Bedroom 2 Bath Ocean view Condo with Full Kitchen, Covered Parking is a condo in Saddlebunch Keys, with pool access, 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, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,939.

From$420/night

Show›

101- Oceanside House with Pool

Holiday Home, Saddlebunch Keys

101- Oceanside House with Pool is a holiday home in Saddlebunch Keys, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 101- Oceanside House with Pool

101- Oceanside House with Pool is a holiday home in Saddlebunch Keys, with pool access, 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, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,084.

From$441/night

Show›

Best Pet-Friendly Vacation Rentals in Saddlebunch Keys, FL

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

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Holiday Home, Saddlebunch Keys

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub! is a holiday home in Saddlebunch Keys, with pet-friendly space, easy beach access, and room for a group. This stay gives…

Read more

About INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub! is a holiday home in Saddlebunch Keys, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,882.

From$269/night

Show›

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Holiday Home, Saddlebunch Keys

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub! is a holiday home in Saddlebunch Keys, with pet-friendly space, easy beach access, and room for a group. This stay gives travelers a…

Read more

About ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub! is a holiday home in Saddlebunch Keys, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,997.

From$285/night

Show›

Coral Palm by AvantStay

Villa, Saddlebunch Keys

Coral Palm by AvantStay is a villa in Saddlebunch Keys, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Coral Palm by AvantStay

Coral Palm by AvantStay is a villa in Saddlebunch Keys, with pet-friendly space and 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, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,373.

From$339/night

Show›

Starlight Serenity - Hideaway with Stunning Views

Holiday Home, Saddlebunch Keys

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Saddlebunch Keys, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

Read more

About Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views is a holiday home in Saddlebunch Keys, 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 $2,416.

From$345/night

Show›

Best Saddlebunch Keys, FL vacation rentals with a kitchen

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

Pelican's Roost, Waterfront comfort at Venture Out

Holiday Home, Saddlebunch Keys

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Saddlebunch Keys, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

Read more

About Pelican's Roost, Waterfront comfort at Venture Out

Pelican's Roost, Waterfront comfort at Venture Out is a holiday home in Saddlebunch Keys, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,954.

From$279/night

Show›

Lower Keys paradise

Holiday Home, Saddlebunch Keys

Lower Keys paradise is a holiday home in Saddlebunch Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Lower Keys paradise

Lower Keys paradise is a holiday home in Saddlebunch Keys, 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 $2,097.

From$300/night

Show›

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Holiday Home, Saddlebunch Keys

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! is a holiday home in Saddlebunch Keys, with pool access, easy beach access, and kitchen access. This stay…

Read more

About Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds! is a holiday home in Saddlebunch Keys, 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 gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,128.

From$304/night

Show›

Paradise Palms in Cudjoe Key #635

Holiday Home, Saddlebunch Keys

Paradise Palms in Cudjoe Key #635 is a holiday home in Saddlebunch Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Paradise Palms in Cudjoe Key #635

Paradise Palms in Cudjoe Key #635 is a holiday home in Saddlebunch Keys, 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: pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,191.

From$313/night

Show›

Our Favorite Family-Friendly Vacation Rentals in Saddlebunch Keys, FL

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

A slice of paradise

Cottage, Saddlebunch Keys

A slice of paradise is a cottage in Saddlebunch Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About A slice of paradise

A slice of paradise is a cottage in Saddlebunch Keys, 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: pool, hot tub, kitchen, and with kitchen.

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

From$274/night

Show›

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cottage, Saddlebunch Keys

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! is a cottage in Saddlebunch Keys, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort! is a cottage in Saddlebunch Keys, 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 $2,088.

From$298/night

Show›

Canal front, dockage, 2 bedroom, 2 bath

Cottage, Saddlebunch Keys

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Saddlebunch Keys, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath is a cottage in Saddlebunch Keys, with pet-friendly space, pool 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, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,224.

From$318/night

Show›

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

Cottage, Saddlebunch Keys

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip · 80’ Pool is a cottage in Saddlebunch Keys, with pool access and room for a group. This stay gives travelers a…

Read more

About **TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip · 80’ Pool is a cottage in Saddlebunch Keys, with pool 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 $2,246.

From$321/night

Show›