Vacation rentals in Boot Key Harbor

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Top-rated vacation rentals in Boot Key Harbor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 119 reviews

4/3 Private Pool w Heater/Dock/Kayaks & more incl.

Our home is close to grocery stores, restaurants and dining, the beach, family-friendly activities, and public transport. You’ll love my place because of the high ceilings, the views, the location, the people, and the ambiance. Our place is good for couples, business travelers, and families (with kids). Included in the rental you'll have access to 4 bicycles for adults and 2 tandem kayaks and 2 paddle boards during your stay. We have a cooler, 2 beach umbrellas and 4 beach chairs for your use.

Jan 4 – 11

$768 per night
Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 140 reviews

Casa Mariposa: Sombrero Beach Neighborhood

Book your getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, selected as 1 0f 24 amazing AirBNB rentals in the Keys, and 1 of 23 Amazing Airbnbs in The Keys. Step out the door from your private suite to a coral path that leads to our 50' heated/cooled lap pool, waterfall and large patio. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in an other lengths of stay.

May 3 – 10

$169 per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 14 reviews

Walk to Sombrero Beach, 50’Dock, SPA, Bikes,Kayaks

Cozy FL Keys stilted beach house ideally located in Sombrero Beach w/ 50’ private dock & large SPA whirlpool & attached bar. Walk/bike to beautiful Sombrero Beach down paved path. 4 bikes, 2 paddle boards, 2 kayaks included. Renovated home with new central A/C unit, new bathrooms & kitchen. Near supermarkets, liquor stores, pharmacy, great restaurants & more. Near Dolphin Research, Aquarium Encounters, Turtle Hospital, Bahia Honda State Park Beaches & more. Key West less than 1 hour away.

Sep 8 – 15

$379 per night

Popular amenities for Boot Key Harbor vacation rentals

Other great vacation rentals in Boot Key Harbor

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 31 reviews

Marathon Beach house w/45’ dock Ocean access

Sep 9 – 16

$350 per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 29 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Oct 23 – 30

$431 per night
Superhost

Home in Marathon

4.96 out of 5 average rating, 23 reviews

Breezy Palms Sombrero Beach

Mar 13 – 20

$500 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 35 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Mar 9 – 16

$545 per night
Guest favorite

Home in Marathon

4.96 out of 5 average rating, 81 reviews

Angler’s Eden

Aug 26 – Sep 2

$608 per night
Guest favorite

Home in Marathon

4.98 out of 5 average rating, 46 reviews

Great Sombrero beach house, many amenities!

Feb 13 – 20

$528 per night
Guest favorite

Home in Marathon

4.94 out of 5 average rating, 18 reviews

Tropical Dream Vacation - 3bdrm/2bath CANAL FRONT!

Aug 19 – 26

$485 per night
Guest favorite

Home in Marathon

4.98 out of 5 average rating, 82 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Sep 28 – Oct 5

$525 per night
Guest favorite

Home in Marathon

4.91 out of 5 average rating, 54 reviews

April/May Avail $295/Blue Ocean Updated 3BR/3.5B

Dec 6 – 13

$324 per night
Guest favorite

Home in Marathon

5.0 out of 5 average rating, 7 reviews

4BR Sombrero Beach House on Canal w Dock & Pool

Sep 13 – 20

$476 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

The Gulf Cottage at Marathon Key

Jun 8 – 15

$127 per night
Superhost

Home in Marathon

4.82 out of 5 average rating, 11 reviews

Beach house w/ Private Dock in Marathon FL

Feb 14 – 21

$300 per night

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  5. Boot Key Harbor