Skyway Living

Pool · Kitchen or Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Summerland Key at Dock Holiday for $174 for your next trip.

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4.9

Outstanding(198 Reviews)

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

Cottage

6 guests · 2 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

Indulge in a peaceful retreat at **TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool, our elegant Cottage in Summerland Key. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Salty Slumber Relaxing 2 bedroom 2 bath Get Away in the Lower Keys

Garden · Pets allowed · Kitchen or Kitchenette

This attractive House in Summerland Key, $108 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront

4.7

Outstanding(13 Reviews)

Pelican's Roost, Waterfront comfort at Venture Out

Garden · Pool · Kitchen or Kitchenette

The best choice in Summerland Key for House, for $174 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.8

Outstanding(226 Reviews)

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

6 guests · 3 bedrooms · 2 baths

Pool · Kitchen or Kitchenette · Air conditioner

This House for $222 in Summerland Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Beachfront

Parrotfish Pointe

Pool · Kitchen or Kitchenette · Air conditioner

Are you ready to indulge in a relaxing getaway? Our House in Summerland Key has everything you need for a rejuvenating stay. Treat yourself to Parrotfish Pointe's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

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4.4

Excellent(14 Reviews)

Tree Top Paradise

Garden · Pool · Pets allowed

This inviting House in Summerland Key can fit your needs for many types of vacations, at $174 per night.

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The Mermaid Manor

Pool · Kitchen or Kitchenette · Air conditioner

This House for $174 in Summerland Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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4.9

Outstanding(196 Reviews)

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

in Cudjoe

6 guests · 2 bedrooms · 2 baths

Pool · Kitchen or Kitchenette · Air conditioner

Experience vacation in Summerland Key with our House, Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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The Blue Marlin

Garden · Pets allowed · Kitchen or Kitchenette

Experience vacation in Summerland Key with our House, The Blue Marlin. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Summerland Canal

Pool · Kitchen or Kitchenette · Air conditioner

Experience the best of Summerland Key with this House available for $78. This property is equipped with amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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Hawkins Lookout

Pets allowed · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Summerland Key? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

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4.8

Outstanding(179 Reviews)

Relax by Florida Keys Beaches, just a 7-min drive away

5 guests · 2 bedrooms · 1 bath

Pool · Pets allowed · Kitchen or Kitchenette

Looking for a memorable stay in Summerland Key? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.

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Turtle Cove Views by Last Key Realty

Pool · Pets allowed · Kitchen or Kitchenette

The best choice in Summerland Key for House, for $174 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Blackbeard`s Hideaway

in Key West

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Summerland Key at Blackbeard`s Hideaway for $174 for your next trip.

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3.9

Good(5 Reviews)

Sunny Place

Apartment

Garden · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our Apartment in Summerland Key has everything you need for a rejuvenating stay. Treat yourself to Sunny Place's exceptional amenities, such as Air conditioner, Internet / Wifi and Laundry.

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4.8

Outstanding(172 Reviews)

Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West

4 guests · 2 bedrooms · 2 baths

Pool · Pets allowed · Kitchen or Kitchenette

Enjoy the best of Summerland Key in our House, Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West . A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Paradise Found

in Key West

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Are you ready to indulge in a relaxing getaway? Our House in Summerland Key has everything you need for a rejuvenating stay. Treat yourself to Paradise Found's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.

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El Paraiso

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House for $174 in Summerland Key, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Start earning One Key rewards

4.9

Outstanding(131 Reviews)

Ocean Front - Private 56' Dock

4 guests · 2 bedrooms · 2 baths

Pool · Kitchen or Kitchenette · Air conditioner

Discover the beauty of Summerland Key with a stay at Ocean Front - Private 56' Dock , a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Love Shack

Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This House in Summerland Key, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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New to VacationRenter

Mermaid Magic by Last Key Realty

Pool · Kitchen or Kitchenette · Air conditioner

This attractive House in Summerland Key, $174 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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New to VacationRenter

Carefree on Cudjoe by Last Key Realty

Pool · Pets allowed · Kitchen or Kitchenette

Enjoy the best of Summerland Key in our House, Carefree on Cudjoe by Last Key Realty. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Start earning One Key rewards

4.7

Outstanding(140 Reviews)

Comfortable Waterfront Vacation Rental

Campground/ RV Resort

4 guests · 2 bedrooms · 1 bath

Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Summerland Key for Campground/ RV Resort, for $254 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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New to VacationRenter

Tidewater Views by Last Key Realty

Pool · Pets allowed · Kitchen or Kitchenette

This inviting House in Summerland Key can fit your needs for many types of vacations, at $174 per night.

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Beachfront

4.5

Excellent(16 Reviews)

NAUTILUS...ocean front cottage retreat ~

Villa

Garden · Pool · Kitchen or Kitchenette

Discover the beauty of Summerland Key with a stay at NAUTILUS...ocean front cottage retreat ~, a top rated Villa with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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4.7

Outstanding(13 Reviews)

OCEANIA... water front cottage retreat ~

Villa

Garden · Pool · Kitchen or Kitchenette

Looking for the perfect place to call home during your trip to Summerland Key? This Villa offers a comfort and style with top-notch amenities, including Air conditioner, Internet / Wifi and Laundry, and more.

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