diff --git a/dev/tasks/python-wheels/osx-build.sh b/dev/tasks/python-wheels/osx-build.sh
index a0bf7b81f5e..e029932ecf6 100755
--- a/dev/tasks/python-wheels/osx-build.sh
+++ b/dev/tasks/python-wheels/osx-build.sh
@@ -75,6 +75,7 @@ function build_wheel {
           -DARROW_PROTOBUF_USE_SHARED=OFF \
           -DARROW_PYTHON=ON \
           -DARROW_RPATH_ORIGIN=ON \
+          -DARROW_S3=${ARROW_S3} \
           -DARROW_VERBOSE_THIRDPARTY_BUILD=ON \
           -DARROW_WITH_BROTLI=ON \
           -DARROW_WITH_BZ2=ON \
@@ -100,18 +101,19 @@ function build_wheel {
     unset ARROW_HOME
     unset PARQUET_HOME
 
+    export PYARROW_BUILD_TYPE='release'
+    export PYARROW_BUNDLE_ARROW_CPP=1
+    export PYARROW_INSTALL_TESTS=1
     export PYARROW_WITH_DATASET=1
     export PYARROW_WITH_FLIGHT=1
+    export PYARROW_WITH_GANDIVA=0
     export PYARROW_WITH_HDFS=1
-    export PYARROW_WITH_PLASMA=1
-    export PYARROW_WITH_PARQUET=1
-    export PYARROW_WITH_ORC=0
     export PYARROW_WITH_JEMALLOC=1
+    export PYARROW_WITH_ORC=0
+    export PYARROW_WITH_PARQUET=1
     export PYARROW_WITH_PLASMA=1
-    export PYARROW_WITH_GANDIVA=0
-    export PYARROW_BUNDLE_ARROW_CPP=1
-    export PYARROW_BUILD_TYPE='release'
-    export PYARROW_INSTALL_TESTS=1
+    export PYARROW_WITH_PLASMA=1
+    export PYARROW_WITH_S3=${ARROW_S3}
     export SETUPTOOLS_SCM_PRETEND_VERSION=$PYARROW_VERSION
     pushd python
     python setup.py build_ext bdist_wheel
@@ -158,4 +160,7 @@ import pyarrow._hdfs
 import pyarrow.dataset
 import pyarrow.flight
 "
+    if [ "$ARROW_S3" = "ON" ]; then
+        python -c "import pyarrow._s3fs"
+    fi
 }
diff --git a/dev/tasks/python-wheels/travis.osx.yml b/dev/tasks/python-wheels/travis.osx.yml
index 172333fd690..99e8591d013 100644
--- a/dev/tasks/python-wheels/travis.osx.yml
+++ b/dev/tasks/python-wheels/travis.osx.yml
@@ -34,7 +34,7 @@ addons:
       - python@3.8
       - thrift
       - wget
-    update: true
+    update: false
 
 # don't build twice
 if: tag IS blank
@@ -45,9 +45,10 @@ env:
     - TRAVIS_TAG={{ task.tag }}
     - PYARROW_VERSION={{ arrow.no_rc_version }}
     - PYARROW_BUILD_VERBOSE=1
-    - MB_PYTHON_VERSION={{ python_version }}
-    - MACOSX_DEPLOYMENT_TARGET="10.9"
     - HOMEBREW_NO_AUTO_UPDATE=1
+    - MB_PYTHON_VERSION={{ python_version }}
+    - MACOSX_DEPLOYMENT_TARGET={{ macos_deployment_target }}
+    - ARROW_S3={{ arrow_s3 }}
 
 before_install:
   - git clone https://github.com/matthew-brett/multibuild
diff --git a/dev/tasks/tasks.yml b/dev/tasks/tasks.yml
index 76ce517cdb0..e4d3d0a6078 100644
--- a/dev/tasks/tasks.yml
+++ b/dev/tasks/tasks.yml
@@ -444,38 +444,88 @@ tasks:
 
   ############################## Wheel OSX ####################################
 
-  wheel-osx-cp35m:
+  wheel-osx-mavericks-cp35m:
     ci: travis
     template: python-wheels/travis.osx.yml
     params:
       python_version: 3.5
+      macos_deployment_target: 10.9
+      arrow_s3: "OFF"
     artifacts:
       - pyarrow-{no_rc_version}-cp35-cp35m-macosx_10_9_intel.whl
 
-  wheel-osx-cp36m:
+  wheel-osx-mavericks-cp36m:
     ci: travis
     template: python-wheels/travis.osx.yml
     params:
       python_version: 3.6
+      macos_deployment_target: 10.9
+      arrow_s3: "OFF"
     artifacts:
       - pyarrow-{no_rc_version}-cp36-cp36m-macosx_10_9_intel.whl
 
-  wheel-osx-cp37m:
+  wheel-osx-mavericks-cp37m:
     ci: travis
     template: python-wheels/travis.osx.yml
     params:
       python_version: 3.7
+      macos_deployment_target: 10.9
+      arrow_s3: "OFF"
     artifacts:
       - pyarrow-{no_rc_version}-cp37-cp37m-macosx_10_9_intel.whl
 
-  wheel-osx-cp38:
+  wheel-osx-mavericks-cp38:
     ci: travis
     template: python-wheels/travis.osx.yml
     params:
       python_version: 3.8
+      macos_deployment_target: 10.9
+      arrow_s3: "OFF"
     artifacts:
       - pyarrow-{no_rc_version}-cp38-cp38-macosx_10_9_x86_64.whl
 
+  # enable S3 support from macOS 10.13 so we don't need to bundle curl, crypt and ssl
+
+  wheel-osx-high-sierra-cp35m:
+    ci: travis
+    template: python-wheels/travis.osx.yml
+    params:
+      python_version: 3.5
+      macos_deployment_target: 10.13
+      arrow_s3: "ON"
+    artifacts:
+      - pyarrow-{no_rc_version}-cp35-cp35m-macosx_10_13_intel.whl
+
+  wheel-osx-high-sierra-cp36m:
+    ci: travis
+    template: python-wheels/travis.osx.yml
+    params:
+      python_version: 3.6
+      macos_deployment_target: 10.13
+      arrow_s3: "ON"
+    artifacts:
+      - pyarrow-{no_rc_version}-cp36-cp36m-macosx_10_13_intel.whl
+
+  wheel-osx-high-sierra-cp37m:
+    ci: travis
+    template: python-wheels/travis.osx.yml
+    params:
+      python_version: 3.7
+      macos_deployment_target: 10.13
+      arrow_s3: "ON"
+    artifacts:
+      - pyarrow-{no_rc_version}-cp37-cp37m-macosx_10_13_intel.whl
+
+  wheel-osx-high-sierra-cp38:
+    ci: travis
+    template: python-wheels/travis.osx.yml
+    params:
+      python_version: 3.8
+      macos_deployment_target: 10.13
+      arrow_s3: "ON"
+    artifacts:
+      - pyarrow-{no_rc_version}-cp38-cp38-macosx_10_13_x86_64.whl
+
   ############################## Wheel Windows ################################
 
   wheel-win-cp35m: